What is the best way to travel from Boston, MA to Chicago?
Looking for a trip? Compare all the available Flights and Buses for the journey to Chicago from Boston, MA. Check between different modes of transportation, look for the cheapest tickets, fastest rides and most popular stations, and see all 2 available companies to find your perfect trip!
What is the cheapest way to reach Chicago from Boston, MA?
You can get to Chicago with just $78 by taking a Flight from United Airlines, but you can find many more cheap offers: we have selected the best ones for next few days here for you.
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Greyhound US25h 55m012:30 PMBoston, MAAtlantic and Beach St1:25 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/20/2026 12:30:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/21/2026 1:25:00 PM. 50 Economy ticket for $112 per person are available. Travel duration is 25h 55m
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FlixBus33h 45m08:55 PMBoston, MAAllston5:40 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Allston, Boston, MA (USA) at 4/20/2026 8:55:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/22/2026 5:40:00 AM. 50 Economy ticket for $113 per person are available. Travel duration is 33h 45m
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FlixBus35h 20m010:00 PMBoston, MAAtlantic and Beach St8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 4/20/2026 10:00:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/22/2026 8:20:00 AM. 50 Economy ticket for $114 per person are available. Travel duration is 35h 20m
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Greyhound US25h 55m012:30 PMBoston, MASouth Station1:25 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from South Station, Boston, MA (USA) at 4/20/2026 12:30:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/21/2026 1:25:00 PM. 50 Economy ticket for $114 per person are available. Travel duration is 25h 55m
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Greyhound US28h 30m03:05 PMBoston, MAAtlantic and Beach St6:35 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/20/2026 3:05:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/21/2026 6:35:00 PM. 50 Economy ticket for $114 per person are available. Travel duration is 28h 30m
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United Airlines3h 0m07:00 AMBoston Logan AirportBoston Logan Airport9:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/20/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/20/2026 9:00:00 AM. 50 Economy ticket for $161 per person are available. Travel duration is 3h 0m
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Spirit Airlines29h 8m08:16 PMBoston Logan AirportBoston Logan Airport12:24 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Spirit Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/20/2026 8:16:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/22/2026 12:24:00 AM. 50 Economy ticket for $172 per person are available. Travel duration is 29h 8m
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Frontier Airlines7h 49m012:42 PMBoston Logan AirportBoston Logan Airport7:31 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/20/2026 12:42:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/20/2026 7:31:00 PM. 50 Economy ticket for $193 per person are available. Travel duration is 7h 49m
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Frontier Airlines21h 58m012:42 PMBoston Logan AirportBoston Logan Airport9:40 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/20/2026 12:42:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/21/2026 9:40:00 AM. 50 Economy ticket for $196 per person are available. Travel duration is 21h 58m
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Sun Country Airlines7h 43m011:17 AMBoston Logan AirportBoston Logan Airport6:00 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Sun Country Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/20/2026 11:17:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/20/2026 6:00:00 PM. 50 Economy ticket for $203 per person are available. Travel duration is 7h 43m
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Spirit Airlines26h 31m06:00 PMBoston Logan AirportBoston Logan Airport7:31 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Spirit Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/20/2026 6:00:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/21/2026 7:31:00 PM. 50 Economy ticket for $205 per person are available. Travel duration is 26h 31m
Cheapest Buses Monday
Cheapest Flights Monday
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Greyhound US29h 50m08:55 AMBoston, MAAtlantic and Beach St1:45 PMChicagoCanal & Van Buren0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/21/2026 8:55:00 AM to Canal & Van Buren, Chicago (USA) arriving at 4/22/2026 1:45:00 PM. 50 Economy ticket for $104 per person are available. Travel duration is 29h 50m
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Greyhound US22h 30m012:30 PMBoston, MAAtlantic and Beach St10:00 AMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/21/2026 12:30:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/22/2026 10:00:00 AM. 50 Economy ticket for $104 per person are available. Travel duration is 22h 30m
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FlixBus28h 40m02:30 AMBoston, MAAtlantic and Beach St6:10 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 4/21/2026 2:30:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/22/2026 6:10:00 AM. 50 Economy ticket for $104 per person are available. Travel duration is 28h 40m
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Greyhound US29h 10m01:30 AMBoston, MAAtlantic and Beach St5:40 AMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/21/2026 1:30:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/22/2026 5:40:00 AM. 50 Economy ticket for $105 per person are available. Travel duration is 29h 10m
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FlixBus33h 20m09:50 PMBoston, MAAtlantic and Beach St6:10 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 4/21/2026 9:50:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/23/2026 6:10:00 AM. 50 Economy ticket for $106 per person are available. Travel duration is 33h 20m
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Spirit Airlines14h 20m08:16 PMBoston Logan AirportBoston Logan Airport9:36 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Spirit Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/21/2026 8:16:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/22/2026 9:36:00 AM. 50 Economy ticket for $111 per person are available. Travel duration is 14h 20m
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Frontier Airlines7h 51m012:40 PMBoston Logan AirportBoston Logan Airport7:31 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/21/2026 12:40:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/21/2026 7:31:00 PM. 50 Economy ticket for $137 per person are available. Travel duration is 7h 51m
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Frontier Airlines12h 0m06:00 AMBoston Logan AirportBoston Logan Airport5:00 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/21/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/21/2026 5:00:00 PM. 50 Economy ticket for $142 per person are available. Travel duration is 12h 0m
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Frontier Airlines17h 14m06:00 AMBoston Logan AirportBoston Logan Airport10:14 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/21/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/21/2026 10:14:00 PM. 50 Economy ticket for $180 per person are available. Travel duration is 17h 14m
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United Airlines5h 13m07:30 PMBoston Logan AirportBoston Logan Airport11:43 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/21/2026 7:30:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/21/2026 11:43:00 PM. 50 Economy ticket for $195 per person are available. Travel duration is 5h 13m
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JetBlue Airways12h 26m08:15 PMBoston Logan AirportBoston Logan Airport7:41 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/21/2026 8:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/22/2026 7:41:00 AM. 50 Economy ticket for $229 per person are available. Travel duration is 12h 26m
Cheapest Buses Tuesday
Cheapest Flights Tuesday
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JetBlue Airways3h 4m07:35 PMBoston Logan AirportBoston Logan Airport9:39 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/22/2026 7:35:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/22/2026 9:39:00 PM. 50 Economy ticket for $88 per person are available. Travel duration is 3h 4m
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United Airlines2h 59m07:15 AMBoston Logan AirportBoston Logan Airport9:14 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/22/2026 7:15:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/22/2026 9:14:00 AM. 50 Economy ticket for $89 per person are available. Travel duration is 2h 59m
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Frontier Airlines7h 36m012:55 PMBoston Logan AirportBoston Logan Airport7:31 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/22/2026 12:55:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/22/2026 7:31:00 PM. 50 Economy ticket for $91 per person are available. Travel duration is 7h 36m
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Frontier Airlines12h 0m06:00 AMBoston Logan AirportBoston Logan Airport5:00 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/22/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/22/2026 5:00:00 PM. 50 Economy ticket for $97 per person are available. Travel duration is 12h 0m
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Spirit Airlines14h 20m08:16 PMBoston Logan AirportBoston Logan Airport9:36 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Spirit Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/22/2026 8:16:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/23/2026 9:36:00 AM. 50 Economy ticket for $111 per person are available. Travel duration is 14h 20m
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Frontier Airlines17h 14m06:00 AMBoston Logan AirportBoston Logan Airport10:14 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/22/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/22/2026 10:14:00 PM. 50 Economy ticket for $147 per person are available. Travel duration is 17h 14m
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FlixBus29h 40m01:30 AMBoston, MAAllston6:10 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Allston, Boston, MA (USA) at 4/22/2026 1:30:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/23/2026 6:10:00 AM. 50 Economy ticket for $111 per person are available. Travel duration is 29h 40m
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FlixBus28h 40m02:30 AMBoston, MAAtlantic and Beach St6:10 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 4/22/2026 2:30:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/23/2026 6:10:00 AM. 50 Economy ticket for $111 per person are available. Travel duration is 28h 40m
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Greyhound US29h 10m01:30 AMBoston, MAAtlantic and Beach St5:40 AMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/22/2026 1:30:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/23/2026 5:40:00 AM. 50 Economy ticket for $112 per person are available. Travel duration is 29h 10m
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Greyhound US29h 50m08:55 AMBoston, MAAtlantic and Beach St1:45 PMChicagoCanal & Van Buren0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/22/2026 8:55:00 AM to Canal & Van Buren, Chicago (USA) arriving at 4/23/2026 1:45:00 PM. 50 Economy ticket for $112 per person are available. Travel duration is 29h 50m
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Greyhound US22h 30m012:30 PMBoston, MAAtlantic and Beach St10:00 AMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/22/2026 12:30:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/23/2026 10:00:00 AM. 50 Economy ticket for $112 per person are available. Travel duration is 22h 30m
Cheapest Flights Wednesday
Cheapest Buses Wednesday
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United Airlines2h 59m06:00 AMBoston Logan AirportBoston Logan Airport7:59 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/23/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/23/2026 7:59:00 AM. 50 Economy ticket for $79 per person are available. Travel duration is 2h 59m
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JetBlue Airways3h 0m07:00 AMBoston Logan AirportBoston Logan Airport9:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/23/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/23/2026 9:00:00 AM. 50 Economy ticket for $88 per person are available. Travel duration is 3h 0m
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Frontier Airlines7h 2m012:31 PMBoston Logan AirportBoston Logan Airport6:33 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/23/2026 12:31:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/23/2026 6:33:00 PM. 50 Economy ticket for $111 per person are available. Travel duration is 7h 2m
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Spirit Airlines13h 39m011:20 AMBoston Logan AirportBoston Logan Airport11:59 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Spirit Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/23/2026 11:20:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/23/2026 11:59:00 PM. 50 Economy ticket for $122 per person are available. Travel duration is 13h 39m
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Frontier Airlines14h 31m06:00 AMBoston Logan AirportBoston Logan Airport7:31 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/23/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/23/2026 7:31:00 PM. 50 Economy ticket for $155 per person are available. Travel duration is 14h 31m
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Spirit Airlines27h 27m03:27 PMBoston Logan AirportBoston Logan Airport5:54 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Spirit Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/23/2026 3:27:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/24/2026 5:54:00 PM. 50 Economy ticket for $166 per person are available. Travel duration is 27h 27m
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Greyhound US28h 30m03:05 PMBoston, MAAtlantic and Beach St6:35 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/23/2026 3:05:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/24/2026 6:35:00 PM. 50 Economy ticket for $96 per person are available. Travel duration is 28h 30m
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Greyhound US25h 55m012:30 PMBoston, MAAtlantic and Beach St1:25 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/23/2026 12:30:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/24/2026 1:25:00 PM. 50 Economy ticket for $98 per person are available. Travel duration is 25h 55m
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Greyhound US31h 50m04:45 PMBoston, MAAtlantic and Beach St11:35 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/23/2026 4:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/24/2026 11:35:00 PM. 50 Economy ticket for $98 per person are available. Travel duration is 31h 50m
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FlixBus35h 20m010:00 PMBoston, MAAtlantic and Beach St8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 4/23/2026 10:00:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/25/2026 8:20:00 AM. 50 Economy ticket for $117 per person are available. Travel duration is 35h 20m
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FlixBus35h 0m010:00 PMBoston, MASouth Station8:00 AMChicagoUnion Station0EconomyA Bus from FlixBus goes from South Station, Boston, MA (USA) at 4/23/2026 10:00:00 PM to Union Station, Chicago (USA) arriving at 4/25/2026 8:00:00 AM. 50 Economy ticket for $117 per person are available. Travel duration is 35h 0m
Cheapest Flights Thursday
Cheapest Buses Thursday
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American Airlines3h 17m05:35 PMBoston Logan AirportBoston Logan Airport7:52 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from American Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/24/2026 5:35:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/24/2026 7:52:00 PM. 50 Economy ticket for $79 per person are available. Travel duration is 3h 17m
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American Airlines2h 50m06:55 PMBoston Logan AirportBoston Logan Airport8:45 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from American Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/24/2026 6:55:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/24/2026 8:45:00 PM. 50 Economy ticket for $79 per person are available. Travel duration is 2h 50m
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United Airlines2h 59m06:00 AMBoston Logan AirportBoston Logan Airport7:59 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/24/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/24/2026 7:59:00 AM. 50 Economy ticket for $80 per person are available. Travel duration is 2h 59m
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United Airlines3h 0m07:00 AMBoston Logan AirportBoston Logan Airport9:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/24/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/24/2026 9:00:00 AM. 50 Economy ticket for $80 per person are available. Travel duration is 3h 0m
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Spirit Airlines18h 59m05:55 AMBoston Logan AirportBoston Logan Airport11:54 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Spirit Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/24/2026 5:55:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/24/2026 11:54:00 PM. 50 Economy ticket for $124 per person are available. Travel duration is 18h 59m
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Spirit Airlines26h 1m08:16 PMBoston Logan AirportBoston Logan Airport9:17 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Spirit Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/24/2026 8:16:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/25/2026 9:17:00 PM. 50 Economy ticket for $124 per person are available. Travel duration is 26h 1m
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Greyhound US28h 30m03:05 PMBoston, MAAtlantic and Beach St6:35 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/24/2026 3:05:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/25/2026 6:35:00 PM. 50 Economy ticket for $113 per person are available. Travel duration is 28h 30m
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Greyhound US31h 5m02:15 AMBoston, MAAtlantic and Beach St8:20 AMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/24/2026 2:15:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/25/2026 8:20:00 AM. 50 Economy ticket for $115 per person are available. Travel duration is 31h 5m
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Greyhound US25h 55m012:30 PMBoston, MAAtlantic and Beach St1:25 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/24/2026 12:30:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/25/2026 1:25:00 PM. 50 Economy ticket for $115 per person are available. Travel duration is 25h 55m
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FlixBus35h 20m010:00 PMBoston, MAAtlantic and Beach St8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 4/24/2026 10:00:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/26/2026 8:20:00 AM. 50 Economy ticket for $118 per person are available. Travel duration is 35h 20m
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FlixBus33h 45m08:55 PMBoston, MAAllston5:40 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Allston, Boston, MA (USA) at 4/24/2026 8:55:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/26/2026 5:40:00 AM. 50 Economy ticket for $119 per person are available. Travel duration is 33h 45m
Cheapest Flights Friday
Cheapest Buses Friday
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United Airlines3h 0m04:28 PMBoston Logan AirportBoston Logan Airport6:28 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/25/2026 4:28:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/25/2026 6:28:00 PM. 50 Economy ticket for $78 per person are available. Travel duration is 3h 0m
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JetBlue Airways3h 4m07:35 PMBoston Logan AirportBoston Logan Airport9:39 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/25/2026 7:35:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/25/2026 9:39:00 PM. 50 Economy ticket for $78 per person are available. Travel duration is 3h 4m
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Spirit Airlines13h 39m011:20 AMBoston Logan AirportBoston Logan Airport11:59 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Spirit Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/25/2026 11:20:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/25/2026 11:59:00 PM. 50 Economy ticket for $113 per person are available. Travel duration is 13h 39m
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Frontier Airlines17h 14m06:00 AMBoston Logan AirportBoston Logan Airport10:14 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/25/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/25/2026 10:14:00 PM. 50 Economy ticket for $136 per person are available. Travel duration is 17h 14m
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Frontier Airlines13h 37m06:00 AMBoston Logan AirportBoston Logan Airport6:37 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/25/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/25/2026 6:37:00 PM. 50 Economy ticket for $141 per person are available. Travel duration is 13h 37m
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Frontier Airlines27h 9m011:06 AMBoston Logan AirportBoston Logan Airport1:15 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/25/2026 11:06:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/26/2026 1:15:00 PM. 50 Economy ticket for $142 per person are available. Travel duration is 27h 9m
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Greyhound US23h 20m03:05 PMBoston, MAAtlantic and Beach St1:25 PMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/25/2026 3:05:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/26/2026 1:25:00 PM. 50 Economy ticket for $119 per person are available. Travel duration is 23h 20m
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FlixBus30h 30m02:30 AMBoston, MAAtlantic and Beach St8:00 AMChicagoCanal & Van Buren0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 4/25/2026 2:30:00 AM to Canal & Van Buren, Chicago (USA) arriving at 4/26/2026 8:00:00 AM. 50 Economy ticket for $119 per person are available. Travel duration is 30h 30m
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Greyhound US22h 30m012:30 PMBoston, MAAtlantic and Beach St10:00 AMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/25/2026 12:30:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/26/2026 10:00:00 AM. 50 Economy ticket for $120 per person are available. Travel duration is 22h 30m
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Greyhound US25h 55m012:30 PMBoston, MAAtlantic and Beach St1:25 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/25/2026 12:30:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/26/2026 1:25:00 PM. 50 Economy ticket for $121 per person are available. Travel duration is 25h 55m
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FlixBus28h 40m02:30 AMBoston, MAAtlantic and Beach St6:10 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 4/25/2026 2:30:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/26/2026 6:10:00 AM. 50 Economy ticket for $121 per person are available. Travel duration is 28h 40m
Cheapest Flights Saturday
Cheapest Buses Saturday
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JetBlue Airways3h 0m07:00 AMBoston Logan AirportBoston Logan Airport9:00 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/26/2026 7:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/26/2026 9:00:00 AM. 50 Economy ticket for $99 per person are available. Travel duration is 3h 0m
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JetBlue Airways3h 0m07:00 AMBoston Logan AirportBoston Logan Airport9:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/26/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/26/2026 9:00:00 AM. 50 Economy ticket for $107 per person are available. Travel duration is 3h 0m
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United Airlines2h 59m06:00 AMBoston Logan AirportBoston Logan Airport7:59 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/26/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/26/2026 7:59:00 AM. 50 Economy ticket for $108 per person are available. Travel duration is 2h 59m
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JetBlue Airways2h 40m010:35 AMBoston Logan AirportBoston Logan Airport12:15 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/26/2026 10:35:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/26/2026 12:15:00 PM. 50 Economy ticket for $109 per person are available. Travel duration is 2h 40m
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Frontier Airlines11h 30m012:31 PMBoston Logan AirportBoston Logan Airport11:01 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/26/2026 12:31:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/26/2026 11:01:00 PM. 50 Economy ticket for $115 per person are available. Travel duration is 11h 30m
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Spirit Airlines20h 5m06:00 PMBoston Logan AirportBoston Logan Airport1:05 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Spirit Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/26/2026 6:00:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/27/2026 1:05:00 PM. 50 Economy ticket for $211 per person are available. Travel duration is 20h 5m
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Greyhound US28h 30m03:05 PMBoston, MAAtlantic and Beach St6:35 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/26/2026 3:05:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/27/2026 6:35:00 PM. 50 Economy ticket for $120 per person are available. Travel duration is 28h 30m
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Greyhound US28h 30m03:05 PMBoston, MASouth Station6:35 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from South Station, Boston, MA (USA) at 4/26/2026 3:05:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/27/2026 6:35:00 PM. 50 Economy ticket for $121 per person are available. Travel duration is 28h 30m
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Greyhound US29h 10m01:30 AMBoston, MAAtlantic and Beach St5:40 AMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/26/2026 1:30:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/27/2026 5:40:00 AM. 50 Economy ticket for $121 per person are available. Travel duration is 29h 10m
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FlixBus30h 50m02:30 AMBoston, MAAtlantic and Beach St8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 4/26/2026 2:30:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/27/2026 8:20:00 AM. 50 Economy ticket for $121 per person are available. Travel duration is 30h 50m
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FlixBus30h 50m02:30 AMBoston, MASouth Station8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from South Station, Boston, MA (USA) at 4/26/2026 2:30:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/27/2026 8:20:00 AM. 50 Economy ticket for $122 per person are available. Travel duration is 30h 50m
Cheapest Flights Sunday
Cheapest Buses Sunday
What are the fastest trips from Boston, MA to Chicago?
You can get to Chicago from Boston, MA in just 2h 40m with a Flight from JetBlue Airways. This is not the only option, and you can click on any of the offers below to compare it with the other modes of transportations.
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United Airlines3h 0m07:00 AMBoston Logan AirportBoston Logan Airport9:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/20/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/20/2026 9:00:00 AM. 50 Economy ticket for $161 per person are available. Travel duration is 3h 0m
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JetBlue Airways3h 0m07:00 AMBoston Logan AirportBoston Logan Airport9:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/20/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/20/2026 9:00:00 AM. 50 Economy ticket for $230 per person are available. Travel duration is 3h 0m
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Sun Country Airlines7h 43m011:17 AMBoston Logan AirportBoston Logan Airport6:00 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Sun Country Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/20/2026 11:17:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/20/2026 6:00:00 PM. 50 Economy ticket for $203 per person are available. Travel duration is 7h 43m
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Frontier Airlines7h 49m012:42 PMBoston Logan AirportBoston Logan Airport7:31 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/20/2026 12:42:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/20/2026 7:31:00 PM. 50 Economy ticket for $193 per person are available. Travel duration is 7h 49m
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Frontier Airlines21h 58m012:42 PMBoston Logan AirportBoston Logan Airport9:40 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/20/2026 12:42:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/21/2026 9:40:00 AM. 50 Economy ticket for $196 per person are available. Travel duration is 21h 58m
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Delta Air Lines23h 21m011:54 AMBoston Logan AirportBoston Logan Airport10:15 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Delta Air Lines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/20/2026 11:54:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/21/2026 10:15:00 AM. 50 Economy ticket for $423 per person are available. Travel duration is 23h 21m
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Greyhound US25h 55m012:30 PMBoston, MAAtlantic and Beach St1:25 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/20/2026 12:30:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/21/2026 1:25:00 PM. 50 Economy ticket for $112 per person are available. Travel duration is 25h 55m
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Greyhound US25h 55m012:30 PMBoston, MASouth Station1:25 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from South Station, Boston, MA (USA) at 4/20/2026 12:30:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/21/2026 1:25:00 PM. 50 Economy ticket for $114 per person are available. Travel duration is 25h 55m
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Greyhound US28h 30m03:05 PMBoston, MAAtlantic and Beach St6:35 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/20/2026 3:05:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/21/2026 6:35:00 PM. 50 Economy ticket for $114 per person are available. Travel duration is 28h 30m
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FlixBus33h 45m08:55 PMBoston, MAAllston5:40 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Allston, Boston, MA (USA) at 4/20/2026 8:55:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/22/2026 5:40:00 AM. 50 Economy ticket for $113 per person are available. Travel duration is 33h 45m
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FlixBus35h 20m010:00 PMBoston, MAAtlantic and Beach St8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 4/20/2026 10:00:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/22/2026 8:20:00 AM. 50 Economy ticket for $114 per person are available. Travel duration is 35h 20m
Fastest Flights Monday
Fastest Buses Monday
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United Airlines5h 13m07:30 PMBoston Logan AirportBoston Logan Airport11:43 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/21/2026 7:30:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/21/2026 11:43:00 PM. 50 Economy ticket for $195 per person are available. Travel duration is 5h 13m
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Frontier Airlines7h 51m012:40 PMBoston Logan AirportBoston Logan Airport7:31 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/21/2026 12:40:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/21/2026 7:31:00 PM. 50 Economy ticket for $137 per person are available. Travel duration is 7h 51m
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Frontier Airlines12h 0m06:00 AMBoston Logan AirportBoston Logan Airport5:00 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/21/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/21/2026 5:00:00 PM. 50 Economy ticket for $142 per person are available. Travel duration is 12h 0m
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JetBlue Airways12h 26m08:15 PMBoston Logan AirportBoston Logan Airport7:41 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/21/2026 8:15:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/22/2026 7:41:00 AM. 50 Economy ticket for $229 per person are available. Travel duration is 12h 26m
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Spirit Airlines14h 20m08:16 PMBoston Logan AirportBoston Logan Airport9:36 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Spirit Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/21/2026 8:16:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/22/2026 9:36:00 AM. 50 Economy ticket for $111 per person are available. Travel duration is 14h 20m
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Frontier Airlines17h 14m06:00 AMBoston Logan AirportBoston Logan Airport10:14 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/21/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/21/2026 10:14:00 PM. 50 Economy ticket for $180 per person are available. Travel duration is 17h 14m
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Greyhound US22h 30m012:30 PMBoston, MAAtlantic and Beach St10:00 AMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/21/2026 12:30:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/22/2026 10:00:00 AM. 50 Economy ticket for $104 per person are available. Travel duration is 22h 30m
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FlixBus28h 40m02:30 AMBoston, MAAtlantic and Beach St6:10 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 4/21/2026 2:30:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/22/2026 6:10:00 AM. 50 Economy ticket for $104 per person are available. Travel duration is 28h 40m
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Greyhound US29h 10m01:30 AMBoston, MAAtlantic and Beach St5:40 AMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/21/2026 1:30:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/22/2026 5:40:00 AM. 50 Economy ticket for $105 per person are available. Travel duration is 29h 10m
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Greyhound US29h 50m08:55 AMBoston, MAAtlantic and Beach St1:45 PMChicagoCanal & Van Buren0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/21/2026 8:55:00 AM to Canal & Van Buren, Chicago (USA) arriving at 4/22/2026 1:45:00 PM. 50 Economy ticket for $104 per person are available. Travel duration is 29h 50m
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FlixBus33h 20m09:50 PMBoston, MAAtlantic and Beach St6:10 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 4/21/2026 9:50:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/23/2026 6:10:00 AM. 50 Economy ticket for $106 per person are available. Travel duration is 33h 20m
Fastest Flights Tuesday
Fastest Buses Tuesday
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United Airlines2h 59m07:15 AMBoston Logan AirportBoston Logan Airport9:14 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/22/2026 7:15:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/22/2026 9:14:00 AM. 50 Economy ticket for $89 per person are available. Travel duration is 2h 59m
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JetBlue Airways3h 4m07:35 PMBoston Logan AirportBoston Logan Airport9:39 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/22/2026 7:35:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/22/2026 9:39:00 PM. 50 Economy ticket for $88 per person are available. Travel duration is 3h 4m
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Frontier Airlines7h 36m012:55 PMBoston Logan AirportBoston Logan Airport7:31 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/22/2026 12:55:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/22/2026 7:31:00 PM. 50 Economy ticket for $91 per person are available. Travel duration is 7h 36m
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Frontier Airlines12h 0m06:00 AMBoston Logan AirportBoston Logan Airport5:00 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/22/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/22/2026 5:00:00 PM. 50 Economy ticket for $97 per person are available. Travel duration is 12h 0m
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Spirit Airlines14h 20m08:16 PMBoston Logan AirportBoston Logan Airport9:36 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Spirit Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/22/2026 8:16:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/23/2026 9:36:00 AM. 50 Economy ticket for $111 per person are available. Travel duration is 14h 20m
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Frontier Airlines14h 31m06:00 AMBoston Logan AirportBoston Logan Airport7:31 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/22/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/22/2026 7:31:00 PM. 50 Economy ticket for $152 per person are available. Travel duration is 14h 31m
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Greyhound US22h 30m012:30 PMBoston, MAAtlantic and Beach St10:00 AMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/22/2026 12:30:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/23/2026 10:00:00 AM. 50 Economy ticket for $112 per person are available. Travel duration is 22h 30m
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FlixBus28h 40m02:30 AMBoston, MAAtlantic and Beach St6:10 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 4/22/2026 2:30:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/23/2026 6:10:00 AM. 50 Economy ticket for $111 per person are available. Travel duration is 28h 40m
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Greyhound US29h 10m01:30 AMBoston, MAAtlantic and Beach St5:40 AMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/22/2026 1:30:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/23/2026 5:40:00 AM. 50 Economy ticket for $112 per person are available. Travel duration is 29h 10m
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FlixBus29h 40m01:30 AMBoston, MAAllston6:10 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Allston, Boston, MA (USA) at 4/22/2026 1:30:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/23/2026 6:10:00 AM. 50 Economy ticket for $111 per person are available. Travel duration is 29h 40m
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Greyhound US29h 50m08:55 AMBoston, MAAtlantic and Beach St1:45 PMChicagoCanal & Van Buren0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/22/2026 8:55:00 AM to Canal & Van Buren, Chicago (USA) arriving at 4/23/2026 1:45:00 PM. 50 Economy ticket for $112 per person are available. Travel duration is 29h 50m
Fastest Flights Wednesday
Fastest Buses Wednesday
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United Airlines2h 59m06:00 AMBoston Logan AirportBoston Logan Airport7:59 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/23/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/23/2026 7:59:00 AM. 50 Economy ticket for $79 per person are available. Travel duration is 2h 59m
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JetBlue Airways3h 0m07:00 AMBoston Logan AirportBoston Logan Airport9:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/23/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/23/2026 9:00:00 AM. 50 Economy ticket for $88 per person are available. Travel duration is 3h 0m
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Frontier Airlines7h 2m012:31 PMBoston Logan AirportBoston Logan Airport6:33 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/23/2026 12:31:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/23/2026 6:33:00 PM. 50 Economy ticket for $111 per person are available. Travel duration is 7h 2m
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Sun Country Airlines8h 1m011:17 AMBoston Logan AirportBoston Logan Airport6:18 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Sun Country Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/23/2026 11:17:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/23/2026 6:18:00 PM. 50 Economy ticket for $242 per person are available. Travel duration is 8h 1m
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Spirit Airlines13h 39m011:20 AMBoston Logan AirportBoston Logan Airport11:59 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Spirit Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/23/2026 11:20:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/23/2026 11:59:00 PM. 50 Economy ticket for $122 per person are available. Travel duration is 13h 39m
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Frontier Airlines14h 31m06:00 AMBoston Logan AirportBoston Logan Airport7:31 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/23/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/23/2026 7:31:00 PM. 50 Economy ticket for $155 per person are available. Travel duration is 14h 31m
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Greyhound US25h 55m012:30 PMBoston, MAAtlantic and Beach St1:25 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/23/2026 12:30:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/24/2026 1:25:00 PM. 50 Economy ticket for $98 per person are available. Travel duration is 25h 55m
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Greyhound US28h 30m03:05 PMBoston, MAAtlantic and Beach St6:35 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/23/2026 3:05:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/24/2026 6:35:00 PM. 50 Economy ticket for $96 per person are available. Travel duration is 28h 30m
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Greyhound US31h 50m04:45 PMBoston, MAAtlantic and Beach St11:35 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/23/2026 4:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/24/2026 11:35:00 PM. 50 Economy ticket for $98 per person are available. Travel duration is 31h 50m
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FlixBus35h 0m010:00 PMBoston, MASouth Station8:00 AMChicagoUnion Station0EconomyA Bus from FlixBus goes from South Station, Boston, MA (USA) at 4/23/2026 10:00:00 PM to Union Station, Chicago (USA) arriving at 4/25/2026 8:00:00 AM. 50 Economy ticket for $117 per person are available. Travel duration is 35h 0m
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FlixBus35h 20m010:00 PMBoston, MAAtlantic and Beach St8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 4/23/2026 10:00:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/25/2026 8:20:00 AM. 50 Economy ticket for $117 per person are available. Travel duration is 35h 20m
Fastest Flights Thursday
Fastest Buses Thursday
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American Airlines2h 50m06:55 PMBoston Logan AirportBoston Logan Airport8:45 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from American Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/24/2026 6:55:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/24/2026 8:45:00 PM. 50 Economy ticket for $79 per person are available. Travel duration is 2h 50m
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United Airlines2h 59m06:00 AMBoston Logan AirportBoston Logan Airport7:59 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/24/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/24/2026 7:59:00 AM. 50 Economy ticket for $80 per person are available. Travel duration is 2h 59m
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United Airlines3h 0m07:00 AMBoston Logan AirportBoston Logan Airport9:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/24/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/24/2026 9:00:00 AM. 50 Economy ticket for $80 per person are available. Travel duration is 3h 0m
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American Airlines3h 17m05:35 PMBoston Logan AirportBoston Logan Airport7:52 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from American Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/24/2026 5:35:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/24/2026 7:52:00 PM. 50 Economy ticket for $79 per person are available. Travel duration is 3h 17m
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Frontier Airlines17h 26m06:00 AMBoston Logan AirportBoston Logan Airport10:26 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/24/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/24/2026 10:26:00 PM. 50 Economy ticket for $156 per person are available. Travel duration is 17h 26m
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Frontier Airlines17h 39m06:00 AMBoston Logan AirportBoston Logan Airport10:39 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/24/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/24/2026 10:39:00 PM. 50 Economy ticket for $156 per person are available. Travel duration is 17h 39m
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Greyhound US25h 55m012:30 PMBoston, MAAtlantic and Beach St1:25 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/24/2026 12:30:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/25/2026 1:25:00 PM. 50 Economy ticket for $115 per person are available. Travel duration is 25h 55m
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Greyhound US28h 30m03:05 PMBoston, MAAtlantic and Beach St6:35 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/24/2026 3:05:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/25/2026 6:35:00 PM. 50 Economy ticket for $113 per person are available. Travel duration is 28h 30m
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Greyhound US31h 5m02:15 AMBoston, MAAtlantic and Beach St8:20 AMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/24/2026 2:15:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/25/2026 8:20:00 AM. 50 Economy ticket for $115 per person are available. Travel duration is 31h 5m
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FlixBus33h 45m08:55 PMBoston, MAAllston5:40 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Allston, Boston, MA (USA) at 4/24/2026 8:55:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/26/2026 5:40:00 AM. 50 Economy ticket for $119 per person are available. Travel duration is 33h 45m
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FlixBus35h 20m010:00 PMBoston, MAAtlantic and Beach St8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 4/24/2026 10:00:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/26/2026 8:20:00 AM. 50 Economy ticket for $118 per person are available. Travel duration is 35h 20m
Fastest Flights Friday
Fastest Buses Friday
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United Airlines3h 0m04:28 PMBoston Logan AirportBoston Logan Airport6:28 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/25/2026 4:28:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/25/2026 6:28:00 PM. 50 Economy ticket for $78 per person are available. Travel duration is 3h 0m
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JetBlue Airways3h 4m07:35 PMBoston Logan AirportBoston Logan Airport9:39 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/25/2026 7:35:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/25/2026 9:39:00 PM. 50 Economy ticket for $78 per person are available. Travel duration is 3h 4m
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Frontier Airlines13h 37m06:00 AMBoston Logan AirportBoston Logan Airport6:37 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/25/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/25/2026 6:37:00 PM. 50 Economy ticket for $141 per person are available. Travel duration is 13h 37m
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Spirit Airlines13h 39m011:20 AMBoston Logan AirportBoston Logan Airport11:59 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Spirit Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/25/2026 11:20:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/25/2026 11:59:00 PM. 50 Economy ticket for $113 per person are available. Travel duration is 13h 39m
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Alaska Airlines13h 52m07:00 AMBoston Logan AirportBoston Logan Airport7:52 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Alaska Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/25/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/25/2026 7:52:00 PM. 50 Economy ticket for $344 per person are available. Travel duration is 13h 52m
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Frontier Airlines17h 14m06:00 AMBoston Logan AirportBoston Logan Airport10:14 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/25/2026 6:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/25/2026 10:14:00 PM. 50 Economy ticket for $136 per person are available. Travel duration is 17h 14m
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Greyhound US22h 30m012:30 PMBoston, MAAtlantic and Beach St10:00 AMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/25/2026 12:30:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/26/2026 10:00:00 AM. 50 Economy ticket for $120 per person are available. Travel duration is 22h 30m
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Greyhound US23h 20m03:05 PMBoston, MAAtlantic and Beach St1:25 PMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/25/2026 3:05:00 PM to Downtown Bus Station, Chicago (USA) arriving at 4/26/2026 1:25:00 PM. 50 Economy ticket for $119 per person are available. Travel duration is 23h 20m
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Greyhound US25h 55m012:30 PMBoston, MAAtlantic and Beach St1:25 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/25/2026 12:30:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/26/2026 1:25:00 PM. 50 Economy ticket for $121 per person are available. Travel duration is 25h 55m
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FlixBus28h 40m02:30 AMBoston, MAAtlantic and Beach St6:10 AMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 4/25/2026 2:30:00 AM to Downtown Bus Station, Chicago (USA) arriving at 4/26/2026 6:10:00 AM. 50 Economy ticket for $121 per person are available. Travel duration is 28h 40m
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FlixBus30h 30m02:30 AMBoston, MAAtlantic and Beach St8:00 AMChicagoCanal & Van Buren0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 4/25/2026 2:30:00 AM to Canal & Van Buren, Chicago (USA) arriving at 4/26/2026 8:00:00 AM. 50 Economy ticket for $119 per person are available. Travel duration is 30h 30m
Fastest Flights Saturday
Fastest Buses Saturday
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JetBlue Airways2h 40m010:35 AMBoston Logan AirportBoston Logan Airport12:15 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/26/2026 10:35:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/26/2026 12:15:00 PM. 50 Economy ticket for $109 per person are available. Travel duration is 2h 40m
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United Airlines2h 59m06:00 AMBoston Logan AirportBoston Logan Airport7:59 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/26/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/26/2026 7:59:00 AM. 50 Economy ticket for $108 per person are available. Travel duration is 2h 59m
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JetBlue Airways3h 0m07:00 AMBoston Logan AirportBoston Logan Airport9:00 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/26/2026 7:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/26/2026 9:00:00 AM. 50 Economy ticket for $99 per person are available. Travel duration is 3h 0m
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JetBlue Airways3h 0m07:00 AMBoston Logan AirportBoston Logan Airport9:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/26/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/26/2026 9:00:00 AM. 50 Economy ticket for $107 per person are available. Travel duration is 3h 0m
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Sun Country Airlines9h 48m09:00 AMBoston Logan AirportBoston Logan Airport5:48 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Sun Country Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/26/2026 9:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 4/26/2026 5:48:00 PM. 50 Economy ticket for $279 per person are available. Travel duration is 9h 48m
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Frontier Airlines10h 51m012:28 PMBoston Logan AirportBoston Logan Airport10:19 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 4/26/2026 12:28:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 4/26/2026 10:19:00 PM. 50 Economy ticket for $246 per person are available. Travel duration is 10h 51m
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Greyhound US28h 30m03:05 PMBoston, MAAtlantic and Beach St6:35 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/26/2026 3:05:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/27/2026 6:35:00 PM. 50 Economy ticket for $120 per person are available. Travel duration is 28h 30m
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Greyhound US28h 30m03:05 PMBoston, MASouth Station6:35 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from South Station, Boston, MA (USA) at 4/26/2026 3:05:00 PM to 95th Red Line Station, Chicago (USA) arriving at 4/27/2026 6:35:00 PM. 50 Economy ticket for $121 per person are available. Travel duration is 28h 30m
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Greyhound US29h 10m01:30 AMBoston, MAAtlantic and Beach St5:40 AMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 4/26/2026 1:30:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/27/2026 5:40:00 AM. 50 Economy ticket for $121 per person are available. Travel duration is 29h 10m
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FlixBus30h 50m02:30 AMBoston, MAAtlantic and Beach St8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 4/26/2026 2:30:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/27/2026 8:20:00 AM. 50 Economy ticket for $121 per person are available. Travel duration is 30h 50m
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FlixBus30h 50m02:30 AMBoston, MASouth Station8:20 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from South Station, Boston, MA (USA) at 4/26/2026 2:30:00 AM to 95th Red Line Station, Chicago (USA) arriving at 4/27/2026 8:20:00 AM. 50 Economy ticket for $122 per person are available. Travel duration is 30h 50m
Fastest Flights Sunday
Fastest Buses Sunday
Here you will find all operators and timetables for a
Bus from Boston, MA to Chicago
What are the most popular stations in Boston, MA and Chicago?
In Boston, MA, you will usually depart from Atlantic and Beach St, Logan Office Center Bus Stop or South Station, while in Chicago you will be arriving at California & 35th Street Bus Stop, Downtown Bus Station or 95th Red Line Station, but there are many more stops to explore in both locations.
How do I decide? Some tips and tricks from our experience
Are you having trouble deciding on how to get to Chicago from Boston, MA? With 15 connections between 2 Flight and Bus operators, it can be difficult to find the one ride that will make you happy. But we have some tips that can help you make the best informed decision. First of all, the best trip is always the one that meets all your needs, so make a list of all the things that you want from this journey and look for something that will satisfy all of them. Here we will go through some of the factors mostly commonly taken into consideration.
Look for the lowest price
Ticket price is usually the main concern: even if you can afford to pay more, why do it if there are cheaper options? Saving on the trip means that you can spend more on the vacation itself! Between Boston, MA and Chicago, you can pay as low as $78 with a Flight from United Airlines.Travel duration
Time is also an important factor. An earlier departure may allow you to see a beautiful sunset or relax before an important event. And remember, time is money, so paying more for a shorter trip may be well worth it. For longer distances, flights are without doubt the best options, but be mindful of airport times and possible delays: a high-speed train may end up cheaper and faster! Here the quicker option is definitely the Flight from JetBlue Airways: you will get to Chicago in just 2h 40m.Comfort makes all the difference
You should always take into account what your personal travelling preferences are. Is one hand luggage enough, or are you trasporting more? Would you like to have a snack during the journey? Can you relax in a busy compartment, or do you need space for yourself? Even among the same mode of transportation, different companies will offer you varying levels of comfort and amenities. The main operators connecting Boston, MA and Chicago are Frontier Airlines, Greyhound US and Spirit Airlines, but be sure to check what they have to offer!Save money with deals, and always compare
One last tip? Even if you live in Boston, MA and Chicago is your only destination, it may be wise to check the offers from and to nearby cities or, if you are flyng, nearby airports. Check the trips from Boston Logan Airport or to Cicero, IL, and look at flights from Boston Logan Airport, and landing at Chicago Midway Airport. Comparing different routes may allow you to find deals or promotions you were not aware of. Consider also signing up to CheckMyBus to see even more exclusive promotions!Which companies offer a trip from Boston, MA to Chicago?
The most popular companies between Boston, MA and Chicago, are Frontier Airlines, Greyhound US and Spirit Airlines. Be sure to check their seat class offers and the amenities that they provide.
Bus companies: Greyhound US and FlixBus
Airlines: Frontier Airlines, Spirit Airlines, JetBlue Airways and 8 more.
All you need to know when you travel from Boston, MA to Chicago
Check all information on comfort and services on all modes of transports from Boston, MA to Chicago. See which seat classes are available, and what amenities are other advantages offered by the operators on your journey.
FAQs about the trip from Boston, MA to Chicago
How can I reach Chicago from Boston, MA?
Every day, there are on average 15 connections between Flight and Bus, with which you can get to Chicago from Boston, MA.
How far is Chicago from Boston, MA?
The distance between Boston, MA and Chicago is 849.6 miles.
What is the most ecofriendly mode of transport between Boston, MA and Chicago?
Trains and buses are by far the greenest options, with trains surpassing buses on longer routes. Planes will always be the worst polluters, especially in shorter flights, were the emissions from the takeoff and landing are less offset by the distance.
On this particular route, a bus will emit, per person, a total of 37 kgs of CO2, a train 48 kgs, a car 232 kgs, and a flight 336 kgs.
What is the cheapest mode of transport from Boston, MA to Chicago?
You can get to Chicago with just $78 by taking a Flight from United Airlines.
What is the fastest way to get from Boston, MA to Chicago?
While a plane is travelling fastest boarding and transfer to airport consumes a lot of time. Usually, high speed trains are better than flights if pure train travel time is below 4 hours. For this particular route, you can get to Chicago in just 2h 40m with a Flight from JetBlue Airways.
More routes to Boston, MA and to Chicago
Looking for more options? Here you can see the most popular routes to Boston, MA and to Chicago. Simply click on a connection, and you’ll find all the details about the route!
