What is the best way to travel from Chicago to Boston, MA?
Looking for a trip? Compare all the available Flights and Buses for the journey to Boston, MA from Chicago. 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 Boston, MA from Chicago?
You can get to Boston, MA with just $81 by taking a Flight from Frontier 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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Frontier Airlines11h 57m012:27 PMChicago Midway AirportChicago Midway Airport1:24 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 6/2/2026 12:27:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/3/2026 1:24:00 AM. 50 Economy ticket for $81 per person are available. Travel duration is 11h 57m
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United Airlines2h 24m06:05 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center9:29 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/2/2026 6:05:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/2/2026 9:29:00 AM. 50 Economy ticket for $83 per person are available. Travel duration is 2h 24m
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JetBlue Airways7h 35m06:15 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center2:50 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/2/2026 6:15:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/2/2026 2:50:00 PM. 50 Economy ticket for $164 per person are available. Travel duration is 7h 35m
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Alaska Airlines14h 34m02:10 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center5:44 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Alaska Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/2/2026 2:10:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/3/2026 5:44:00 AM. 50 Economy ticket for $260 per person are available. Travel duration is 14h 34m
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Spirit Airlines8h 6m010:54 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center8:00 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Spirit Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/2/2026 10:54:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/2/2026 8:00:00 PM. 50 Economy ticket for $454 per person are available. Travel duration is 8h 6m
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Greyhound US27h 25m07:00 AMChicagoDowntown Bus Station11:25 AMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/2/2026 7:00:00 AM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/3/2026 11:25:00 AM. 50 Economy ticket for $130 per person are available. Travel duration is 27h 25m
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Greyhound US23h 25m06:00 PMChicagoDowntown Bus Station6:25 PMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/2/2026 6:00:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/3/2026 6:25:00 PM. 50 Economy ticket for $130 per person are available. Travel duration is 23h 25m
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Greyhound US33h 15m011:10 PMChicagoCanal & Van Buren9:25 AMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Canal & Van Buren, Chicago (USA) at 6/2/2026 11:10:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/4/2026 9:25:00 AM. 50 Economy ticket for $130 per person are available. Travel duration is 33h 15m
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FlixBus23h 30m012:25 PMChicagoDowntown Bus Station12:55 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/2/2026 12:25:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/3/2026 12:55:00 PM. 50 Economy ticket for $130 per person are available. Travel duration is 23h 30m
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FlixBus23h 30m012:25 PMChicagoDowntown Bus Station12:55 PMBoston, MASouth Station0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/2/2026 12:25:00 PM to South Station, Boston, MA (USA) arriving at 6/3/2026 12:55:00 PM. 50 Economy ticket for $131 per person are available. Travel duration is 23h 30m
Cheapest Flights Tuesday
Cheapest Buses Tuesday
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JetBlue Airways2h 30m08:50 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center12:20 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/3/2026 8:50:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/3/2026 12:20:00 PM. 50 Economy ticket for $81 per person are available. Travel duration is 2h 30m
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United Airlines2h 24m06:05 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center9:29 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/3/2026 6:05:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/3/2026 9:29:00 AM. 50 Economy ticket for $83 per person are available. Travel duration is 2h 24m
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United Airlines2h 35m03:55 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center7:30 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/3/2026 3:55:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/3/2026 7:30:00 PM. 50 Economy ticket for $83 per person are available. Travel duration is 2h 35m
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Frontier Airlines12h 20m012:04 PMChicago Midway AirportChicago Midway Airport1:24 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 6/3/2026 12:04:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/4/2026 1:24:00 AM. 50 Economy ticket for $95 per person are available. Travel duration is 12h 20m
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Frontier Airlines24h 49m06:00 AMChicago Midway AirportChicago Midway Airport7:49 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 6/3/2026 6:00:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/4/2026 7:49:00 AM. 50 Economy ticket for $107 per person are available. Travel duration is 24h 49m
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Greyhound US23h 25m06:00 PMChicagoDowntown Bus Station6:25 PMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/3/2026 6:00:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/4/2026 6:25:00 PM. 50 Economy ticket for $106 per person are available. Travel duration is 23h 25m
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FlixBus25h 35m07:15 PMChicagoDowntown Bus Station9:50 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/3/2026 7:15:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/4/2026 9:50:00 PM. 50 Economy ticket for $107 per person are available. Travel duration is 25h 35m
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Greyhound US27h 25m07:00 AMChicagoDowntown Bus Station11:25 AMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/3/2026 7:00:00 AM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/4/2026 11:25:00 AM. 50 Economy ticket for $109 per person are available. Travel duration is 27h 25m
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Greyhound US23h 25m06:00 PMChicagoDowntown Bus Station6:25 PMBoston, MASouth Station0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/3/2026 6:00:00 PM to South Station, Boston, MA (USA) arriving at 6/4/2026 6:25:00 PM. 50 Economy ticket for $110 per person are available. Travel duration is 23h 25m
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FlixBus25h 35m07:15 PMChicagoDowntown Bus Station9:50 PMBoston, MASouth Station0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/3/2026 7:15:00 PM to South Station, Boston, MA (USA) arriving at 6/4/2026 9:50:00 PM. 50 Economy ticket for $111 per person are available. Travel duration is 25h 35m
Cheapest Flights Wednesday
Cheapest Buses Wednesday
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Greyhound US23h 25m06:00 PMChicagoDowntown Bus Station6:25 PMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/4/2026 6:00:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/5/2026 6:25:00 PM. 50 Economy ticket for $88 per person are available. Travel duration is 23h 25m
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FlixBus25h 35m07:15 PMChicagoDowntown Bus Station9:50 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/4/2026 7:15:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/5/2026 9:50:00 PM. 50 Economy ticket for $89 per person are available. Travel duration is 25h 35m
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FlixBus22h 35m012:25 PMChicagoDowntown Bus Station12:00 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/4/2026 12:25:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/5/2026 12:00:00 PM. 50 Economy ticket for $90 per person are available. Travel duration is 22h 35m
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Greyhound US27h 25m07:00 AMChicagoDowntown Bus Station11:25 AMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/4/2026 7:00:00 AM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/5/2026 11:25:00 AM. 50 Economy ticket for $93 per person are available. Travel duration is 27h 25m
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FlixBus23h 55m011:05 AMChicago95th Red Line Station12:00 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 6/4/2026 11:05:00 AM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/5/2026 12:00:00 PM. 50 Economy ticket for $95 per person are available. Travel duration is 23h 55m
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United Airlines2h 24m06:05 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center9:29 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/4/2026 6:05:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/4/2026 9:29:00 AM. 50 Economy ticket for $89 per person are available. Travel duration is 2h 24m
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JetBlue Airways2h 29m08:30 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center11:59 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/4/2026 8:30:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/4/2026 11:59:00 PM. 50 Economy ticket for $96 per person are available. Travel duration is 2h 29m
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Frontier Airlines17h 29m06:55 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center1:24 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/4/2026 6:55:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/5/2026 1:24:00 AM. 50 Economy ticket for $110 per person are available. Travel duration is 17h 29m
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Sun Country Airlines14h 8m06:25 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center9:33 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Sun Country Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/4/2026 6:25:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/5/2026 9:33:00 AM. 50 Economy ticket for $240 per person are available. Travel duration is 14h 8m
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Alaska Airlines14h 34m02:10 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center5:44 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Alaska Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/4/2026 2:10:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/5/2026 5:44:00 AM. 50 Economy ticket for $363 per person are available. Travel duration is 14h 34m
Cheapest Buses Thursday
Cheapest Flights Thursday
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JetBlue Airways2h 29m08:30 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center11:59 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/5/2026 8:30:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/5/2026 11:59:00 PM. 50 Economy ticket for $86 per person are available. Travel duration is 2h 29m
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United Airlines2h 36m06:20 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center9:56 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/5/2026 6:20:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/5/2026 9:56:00 PM. 50 Economy ticket for $88 per person are available. Travel duration is 2h 36m
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Frontier Airlines12h 20m012:04 PMChicago Midway AirportChicago Midway Airport1:24 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 6/5/2026 12:04:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/6/2026 1:24:00 AM. 50 Economy ticket for $120 per person are available. Travel duration is 12h 20m
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Allegiant Air11h 41m09:23 PMChicago Midway AirportChicago Midway Airport10:04 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Allegiant Air goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 6/5/2026 9:23:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/6/2026 10:04:00 AM. 50 Economy ticket for $133 per person are available. Travel duration is 11h 41m
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Sun Country Airlines15h 13m06:25 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center10:38 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Sun Country Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/5/2026 6:25:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/6/2026 10:38:00 AM. 50 Economy ticket for $248 per person are available. Travel duration is 15h 13m
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Greyhound US23h 25m06:00 PMChicagoDowntown Bus Station6:25 PMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/5/2026 6:00:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/6/2026 6:25:00 PM. 50 Economy ticket for $126 per person are available. Travel duration is 23h 25m
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Greyhound US28h 40m06:00 PMChicagoDowntown Bus Station11:40 PMBoston, MAAllston0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/5/2026 6:00:00 PM to Allston, Boston, MA (USA) arriving at 6/6/2026 11:40:00 PM. 50 Economy ticket for $126 per person are available. Travel duration is 28h 40m
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FlixBus22h 35m012:25 PMChicagoDowntown Bus Station12:00 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/5/2026 12:25:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/6/2026 12:00:00 PM. 50 Economy ticket for $126 per person are available. Travel duration is 22h 35m
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Greyhound US27h 25m07:00 AMChicagoDowntown Bus Station11:25 AMBoston, MASouth Station0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/5/2026 7:00:00 AM to South Station, Boston, MA (USA) arriving at 6/6/2026 11:25:00 AM. 50 Economy ticket for $127 per person are available. Travel duration is 27h 25m
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FlixBus22h 35m012:25 PMChicagoDowntown Bus Station12:00 PMBoston, MASouth Station0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/5/2026 12:25:00 PM to South Station, Boston, MA (USA) arriving at 6/6/2026 12:00:00 PM. 50 Economy ticket for $127 per person are available. Travel duration is 22h 35m
Cheapest Flights Friday
Cheapest Buses Friday
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United Airlines2h 34m01:55 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center5:29 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/6/2026 1:55:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/6/2026 5:29:00 PM. 50 Economy ticket for $97 per person are available. Travel duration is 2h 34m
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United Airlines2h 35m03:55 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center7:30 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/6/2026 3:55:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/6/2026 7:30:00 PM. 50 Economy ticket for $97 per person are available. Travel duration is 2h 35m
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Frontier Airlines12h 25m011:59 AMChicago Midway AirportChicago Midway Airport1:24 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 6/6/2026 11:59:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/7/2026 1:24:00 AM. 50 Economy ticket for $113 per person are available. Travel duration is 12h 25m
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Frontier Airlines10h 55m01:29 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center1:24 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/6/2026 1:29:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/7/2026 1:24:00 AM. 50 Economy ticket for $113 per person are available. Travel duration is 10h 55m
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JetBlue Airways2h 29m01:55 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center5:24 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/6/2026 1:55:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/6/2026 5:24:00 PM. 50 Economy ticket for $131 per person are available. Travel duration is 2h 29m
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Greyhound US27h 25m07:00 AMChicagoDowntown Bus Station11:25 AMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/6/2026 7:00:00 AM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/7/2026 11:25:00 AM. 50 Economy ticket for $127 per person are available. Travel duration is 27h 25m
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Greyhound US27h 25m07:00 AMChicagoDowntown Bus Station11:25 AMBoston, MASouth Station0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/6/2026 7:00:00 AM to South Station, Boston, MA (USA) arriving at 6/7/2026 11:25:00 AM. 50 Economy ticket for $128 per person are available. Travel duration is 27h 25m
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FlixBus33h 25m07:15 PMChicagoDowntown Bus Station5:40 AMBoston, MAAllston0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/6/2026 7:15:00 PM to Allston, Boston, MA (USA) arriving at 6/8/2026 5:40:00 AM. 50 Economy ticket for $142 per person are available. Travel duration is 33h 25m
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Greyhound US33h 15m011:10 PMChicagoUnion Station9:25 AMBoston, MASouth Station0EconomyA Bus from Greyhound US goes from Union Station, Chicago (USA) at 6/6/2026 11:10:00 PM to South Station, Boston, MA (USA) arriving at 6/8/2026 9:25:00 AM. 50 Economy ticket for $151 per person are available. Travel duration is 33h 15m
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FlixBus25h 35m07:15 PMChicagoDowntown Bus Station9:50 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/6/2026 7:15:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/7/2026 9:50:00 PM. 50 Economy ticket for $153 per person are available. Travel duration is 25h 35m
Cheapest Flights Saturday
Cheapest Buses Saturday
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Greyhound US23h 25m06:00 PMChicagoDowntown Bus Station6:25 PMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/7/2026 6:00:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/8/2026 6:25:00 PM. 50 Economy ticket for $110 per person are available. Travel duration is 23h 25m
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Greyhound US23h 25m06:00 PMChicagoDowntown Bus Station6:25 PMBoston, MASouth Station0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/7/2026 6:00:00 PM to South Station, Boston, MA (USA) arriving at 6/8/2026 6:25:00 PM. 50 Economy ticket for $111 per person are available. Travel duration is 23h 25m
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FlixBus23h 55m011:05 AMChicago95th Red Line Station12:00 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 6/7/2026 11:05:00 AM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/8/2026 12:00:00 PM. 50 Economy ticket for $111 per person are available. Travel duration is 23h 55m
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Greyhound US27h 25m07:00 AMChicagoDowntown Bus Station11:25 AMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/7/2026 7:00:00 AM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/8/2026 11:25:00 AM. 50 Economy ticket for $112 per person are available. Travel duration is 27h 25m
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FlixBus22h 35m012:25 PMChicagoDowntown Bus Station12:00 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/7/2026 12:25:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/8/2026 12:00:00 PM. 50 Economy ticket for $112 per person are available. Travel duration is 22h 35m
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United Airlines2h 24m06:05 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center9:29 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/7/2026 6:05:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/7/2026 9:29:00 AM. 50 Economy ticket for $119 per person are available. Travel duration is 2h 24m
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Frontier Airlines24h 49m06:00 AMChicago Midway AirportChicago Midway Airport7:49 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 6/7/2026 6:00:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/8/2026 7:49:00 AM. 50 Economy ticket for $229 per person are available. Travel duration is 24h 49m
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Sun Country Airlines15h 17m06:39 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center10:56 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Sun Country Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/7/2026 6:39:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/8/2026 10:56:00 AM. 50 Economy ticket for $288 per person are available. Travel duration is 15h 17m
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JetBlue Airways2h 30m08:49 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center12:19 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/7/2026 8:49:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/7/2026 12:19:00 PM. 50 Economy ticket for $315 per person are available. Travel duration is 2h 30m
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Alaska Airlines19h 44m09:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center5:44 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Alaska Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/7/2026 9:00:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/8/2026 5:44:00 AM. 50 Economy ticket for $344 per person are available. Travel duration is 19h 44m
Cheapest Buses Sunday
Cheapest Flights Sunday
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United Airlines2h 33m09:41 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center1:14 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/8/2026 9:41:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/9/2026 1:14:00 AM. 50 Economy ticket for $97 per person are available. Travel duration is 2h 33m
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JetBlue Airways2h 29m08:30 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center11:59 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/8/2026 8:30:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/8/2026 11:59:00 PM. 50 Economy ticket for $111 per person are available. Travel duration is 2h 29m
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Frontier Airlines18h 48m012:04 PMChicago Midway AirportChicago Midway Airport7:52 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 6/8/2026 12:04:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/9/2026 7:52:00 AM. 50 Economy ticket for $159 per person are available. Travel duration is 18h 48m
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Sun Country Airlines14h 29m07:09 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center10:38 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Sun Country Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/8/2026 7:09:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/9/2026 10:38:00 AM. 50 Economy ticket for $295 per person are available. Travel duration is 14h 29m
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Alaska Airlines14h 34m02:10 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center5:44 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Alaska Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/8/2026 2:10:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/9/2026 5:44:00 AM. 50 Economy ticket for $343 per person are available. Travel duration is 14h 34m
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Greyhound US27h 25m07:00 AMChicagoDowntown Bus Station11:25 AMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/8/2026 7:00:00 AM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/9/2026 11:25:00 AM. 50 Economy ticket for $102 per person are available. Travel duration is 27h 25m
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Greyhound US23h 25m06:00 PMChicagoDowntown Bus Station6:25 PMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/8/2026 6:00:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/9/2026 6:25:00 PM. 50 Economy ticket for $102 per person are available. Travel duration is 23h 25m
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Greyhound US27h 25m07:00 AMChicagoDowntown Bus Station11:25 AMBoston, MASouth Station0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/8/2026 7:00:00 AM to South Station, Boston, MA (USA) arriving at 6/9/2026 11:25:00 AM. 50 Economy ticket for $104 per person are available. Travel duration is 27h 25m
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FlixBus25h 35m07:15 PMChicagoDowntown Bus Station9:50 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/8/2026 7:15:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/9/2026 9:50:00 PM. 50 Economy ticket for $104 per person are available. Travel duration is 25h 35m
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FlixBus25h 35m07:15 PMChicagoDowntown Bus Station9:50 PMBoston, MASouth Station0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/8/2026 7:15:00 PM to South Station, Boston, MA (USA) arriving at 6/9/2026 9:50:00 PM. 50 Economy ticket for $105 per person are available. Travel duration is 25h 35m
Cheapest Flights Monday
Cheapest Buses Monday
What are the fastest trips from Chicago to Boston, MA?
You can get to Boston, MA from Chicago in just 2h 24m with a Flight from United Airlines. 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 Airlines2h 24m06:05 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center9:29 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/2/2026 6:05:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/2/2026 9:29:00 AM. 50 Economy ticket for $83 per person are available. Travel duration is 2h 24m
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JetBlue Airways7h 35m06:15 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center2:50 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/2/2026 6:15:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/2/2026 2:50:00 PM. 50 Economy ticket for $164 per person are available. Travel duration is 7h 35m
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Spirit Airlines8h 6m010:54 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center8:00 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Spirit Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/2/2026 10:54:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/2/2026 8:00:00 PM. 50 Economy ticket for $454 per person are available. Travel duration is 8h 6m
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Frontier Airlines11h 57m012:27 PMChicago Midway AirportChicago Midway Airport1:24 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 6/2/2026 12:27:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/3/2026 1:24:00 AM. 50 Economy ticket for $81 per person are available. Travel duration is 11h 57m
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Alaska Airlines14h 34m02:10 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center5:44 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Alaska Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/2/2026 2:10:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/3/2026 5:44:00 AM. 50 Economy ticket for $260 per person are available. Travel duration is 14h 34m
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Greyhound US23h 25m06:00 PMChicagoDowntown Bus Station6:25 PMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/2/2026 6:00:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/3/2026 6:25:00 PM. 50 Economy ticket for $130 per person are available. Travel duration is 23h 25m
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FlixBus23h 30m012:25 PMChicagoDowntown Bus Station12:55 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/2/2026 12:25:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/3/2026 12:55:00 PM. 50 Economy ticket for $130 per person are available. Travel duration is 23h 30m
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FlixBus23h 30m012:25 PMChicagoDowntown Bus Station12:55 PMBoston, MASouth Station0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/2/2026 12:25:00 PM to South Station, Boston, MA (USA) arriving at 6/3/2026 12:55:00 PM. 50 Economy ticket for $131 per person are available. Travel duration is 23h 30m
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Greyhound US27h 25m07:00 AMChicagoDowntown Bus Station11:25 AMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/2/2026 7:00:00 AM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/3/2026 11:25:00 AM. 50 Economy ticket for $130 per person are available. Travel duration is 27h 25m
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Greyhound US33h 15m011:10 PMChicagoCanal & Van Buren9:25 AMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Canal & Van Buren, Chicago (USA) at 6/2/2026 11:10:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/4/2026 9:25:00 AM. 50 Economy ticket for $130 per person are available. Travel duration is 33h 15m
Fastest Flights Tuesday
Fastest Buses Tuesday
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United Airlines2h 24m06:05 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center9:29 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/3/2026 6:05:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/3/2026 9:29:00 AM. 50 Economy ticket for $83 per person are available. Travel duration is 2h 24m
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JetBlue Airways2h 30m08:50 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center12:20 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/3/2026 8:50:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/3/2026 12:20:00 PM. 50 Economy ticket for $81 per person are available. Travel duration is 2h 30m
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United Airlines2h 35m03:55 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center7:30 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/3/2026 3:55:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/3/2026 7:30:00 PM. 50 Economy ticket for $83 per person are available. Travel duration is 2h 35m
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Frontier Airlines12h 20m012:04 PMChicago Midway AirportChicago Midway Airport1:24 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 6/3/2026 12:04:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/4/2026 1:24:00 AM. 50 Economy ticket for $95 per person are available. Travel duration is 12h 20m
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Frontier Airlines24h 49m06:00 AMChicago Midway AirportChicago Midway Airport7:49 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 6/3/2026 6:00:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/4/2026 7:49:00 AM. 50 Economy ticket for $107 per person are available. Travel duration is 24h 49m
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Greyhound US23h 25m06:00 PMChicagoDowntown Bus Station6:25 PMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/3/2026 6:00:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/4/2026 6:25:00 PM. 50 Economy ticket for $106 per person are available. Travel duration is 23h 25m
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Greyhound US23h 25m06:00 PMChicagoDowntown Bus Station6:25 PMBoston, MASouth Station0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/3/2026 6:00:00 PM to South Station, Boston, MA (USA) arriving at 6/4/2026 6:25:00 PM. 50 Economy ticket for $110 per person are available. Travel duration is 23h 25m
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FlixBus25h 35m07:15 PMChicagoDowntown Bus Station9:50 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/3/2026 7:15:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/4/2026 9:50:00 PM. 50 Economy ticket for $107 per person are available. Travel duration is 25h 35m
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FlixBus25h 35m07:15 PMChicagoDowntown Bus Station9:50 PMBoston, MASouth Station0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/3/2026 7:15:00 PM to South Station, Boston, MA (USA) arriving at 6/4/2026 9:50:00 PM. 50 Economy ticket for $111 per person are available. Travel duration is 25h 35m
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Greyhound US27h 25m07:00 AMChicagoDowntown Bus Station11:25 AMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/3/2026 7:00:00 AM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/4/2026 11:25:00 AM. 50 Economy ticket for $109 per person are available. Travel duration is 27h 25m
Fastest Flights Wednesday
Fastest Buses Wednesday
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United Airlines2h 24m06:05 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center9:29 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/4/2026 6:05:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/4/2026 9:29:00 AM. 50 Economy ticket for $89 per person are available. Travel duration is 2h 24m
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JetBlue Airways2h 29m08:30 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center11:59 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/4/2026 8:30:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/4/2026 11:59:00 PM. 50 Economy ticket for $96 per person are available. Travel duration is 2h 29m
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Sun Country Airlines14h 8m06:25 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center9:33 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Sun Country Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/4/2026 6:25:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/5/2026 9:33:00 AM. 50 Economy ticket for $240 per person are available. Travel duration is 14h 8m
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Alaska Airlines14h 34m02:10 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center5:44 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Alaska Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/4/2026 2:10:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/5/2026 5:44:00 AM. 50 Economy ticket for $363 per person are available. Travel duration is 14h 34m
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Frontier Airlines17h 29m06:55 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center1:24 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/4/2026 6:55:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/5/2026 1:24:00 AM. 50 Economy ticket for $110 per person are available. Travel duration is 17h 29m
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FlixBus22h 35m012:25 PMChicagoDowntown Bus Station12:00 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/4/2026 12:25:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/5/2026 12:00:00 PM. 50 Economy ticket for $90 per person are available. Travel duration is 22h 35m
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Greyhound US23h 25m06:00 PMChicagoDowntown Bus Station6:25 PMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/4/2026 6:00:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/5/2026 6:25:00 PM. 50 Economy ticket for $88 per person are available. Travel duration is 23h 25m
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FlixBus23h 55m011:05 AMChicago95th Red Line Station12:00 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 6/4/2026 11:05:00 AM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/5/2026 12:00:00 PM. 50 Economy ticket for $95 per person are available. Travel duration is 23h 55m
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FlixBus25h 35m07:15 PMChicagoDowntown Bus Station9:50 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/4/2026 7:15:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/5/2026 9:50:00 PM. 50 Economy ticket for $89 per person are available. Travel duration is 25h 35m
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Greyhound US27h 25m07:00 AMChicagoDowntown Bus Station11:25 AMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/4/2026 7:00:00 AM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/5/2026 11:25:00 AM. 50 Economy ticket for $93 per person are available. Travel duration is 27h 25m
Fastest Flights Thursday
Fastest Buses Thursday
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JetBlue Airways2h 29m08:30 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center11:59 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/5/2026 8:30:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/5/2026 11:59:00 PM. 50 Economy ticket for $86 per person are available. Travel duration is 2h 29m
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United Airlines2h 36m06:20 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center9:56 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/5/2026 6:20:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/5/2026 9:56:00 PM. 50 Economy ticket for $88 per person are available. Travel duration is 2h 36m
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Allegiant Air11h 41m09:23 PMChicago Midway AirportChicago Midway Airport10:04 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Allegiant Air goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 6/5/2026 9:23:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/6/2026 10:04:00 AM. 50 Economy ticket for $133 per person are available. Travel duration is 11h 41m
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Frontier Airlines12h 20m012:04 PMChicago Midway AirportChicago Midway Airport1:24 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 6/5/2026 12:04:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/6/2026 1:24:00 AM. 50 Economy ticket for $120 per person are available. Travel duration is 12h 20m
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Sun Country Airlines15h 13m06:25 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center10:38 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Sun Country Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/5/2026 6:25:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/6/2026 10:38:00 AM. 50 Economy ticket for $248 per person are available. Travel duration is 15h 13m
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FlixBus22h 35m012:25 PMChicagoDowntown Bus Station12:00 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/5/2026 12:25:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/6/2026 12:00:00 PM. 50 Economy ticket for $126 per person are available. Travel duration is 22h 35m
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FlixBus22h 35m012:25 PMChicagoDowntown Bus Station12:00 PMBoston, MASouth Station0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/5/2026 12:25:00 PM to South Station, Boston, MA (USA) arriving at 6/6/2026 12:00:00 PM. 50 Economy ticket for $127 per person are available. Travel duration is 22h 35m
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Greyhound US23h 25m06:00 PMChicagoDowntown Bus Station6:25 PMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/5/2026 6:00:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/6/2026 6:25:00 PM. 50 Economy ticket for $126 per person are available. Travel duration is 23h 25m
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Greyhound US27h 25m07:00 AMChicagoDowntown Bus Station11:25 AMBoston, MASouth Station0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/5/2026 7:00:00 AM to South Station, Boston, MA (USA) arriving at 6/6/2026 11:25:00 AM. 50 Economy ticket for $127 per person are available. Travel duration is 27h 25m
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Greyhound US28h 40m06:00 PMChicagoDowntown Bus Station11:40 PMBoston, MAAllston0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/5/2026 6:00:00 PM to Allston, Boston, MA (USA) arriving at 6/6/2026 11:40:00 PM. 50 Economy ticket for $126 per person are available. Travel duration is 28h 40m
Fastest Flights Friday
Fastest Buses Friday
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JetBlue Airways2h 29m01:55 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center5:24 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/6/2026 1:55:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/6/2026 5:24:00 PM. 50 Economy ticket for $131 per person are available. Travel duration is 2h 29m
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United Airlines2h 34m01:55 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center5:29 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/6/2026 1:55:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/6/2026 5:29:00 PM. 50 Economy ticket for $97 per person are available. Travel duration is 2h 34m
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United Airlines2h 35m03:55 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center7:30 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/6/2026 3:55:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/6/2026 7:30:00 PM. 50 Economy ticket for $97 per person are available. Travel duration is 2h 35m
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Frontier Airlines10h 55m01:29 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center1:24 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/6/2026 1:29:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/7/2026 1:24:00 AM. 50 Economy ticket for $113 per person are available. Travel duration is 10h 55m
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Frontier Airlines12h 25m011:59 AMChicago Midway AirportChicago Midway Airport1:24 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 6/6/2026 11:59:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/7/2026 1:24:00 AM. 50 Economy ticket for $113 per person are available. Travel duration is 12h 25m
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FlixBus25h 35m07:15 PMChicagoDowntown Bus Station9:50 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/6/2026 7:15:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/7/2026 9:50:00 PM. 50 Economy ticket for $153 per person are available. Travel duration is 25h 35m
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Greyhound US27h 25m07:00 AMChicagoDowntown Bus Station11:25 AMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/6/2026 7:00:00 AM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/7/2026 11:25:00 AM. 50 Economy ticket for $127 per person are available. Travel duration is 27h 25m
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Greyhound US27h 25m07:00 AMChicagoDowntown Bus Station11:25 AMBoston, MASouth Station0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/6/2026 7:00:00 AM to South Station, Boston, MA (USA) arriving at 6/7/2026 11:25:00 AM. 50 Economy ticket for $128 per person are available. Travel duration is 27h 25m
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Greyhound US33h 15m011:10 PMChicagoUnion Station9:25 AMBoston, MASouth Station0EconomyA Bus from Greyhound US goes from Union Station, Chicago (USA) at 6/6/2026 11:10:00 PM to South Station, Boston, MA (USA) arriving at 6/8/2026 9:25:00 AM. 50 Economy ticket for $151 per person are available. Travel duration is 33h 15m
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FlixBus33h 25m07:15 PMChicagoDowntown Bus Station5:40 AMBoston, MAAllston0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/6/2026 7:15:00 PM to Allston, Boston, MA (USA) arriving at 6/8/2026 5:40:00 AM. 50 Economy ticket for $142 per person are available. Travel duration is 33h 25m
Fastest Flights Saturday
Fastest Buses Saturday
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United Airlines2h 24m06:05 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center9:29 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/7/2026 6:05:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/7/2026 9:29:00 AM. 50 Economy ticket for $119 per person are available. Travel duration is 2h 24m
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JetBlue Airways2h 30m08:49 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center12:19 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/7/2026 8:49:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/7/2026 12:19:00 PM. 50 Economy ticket for $315 per person are available. Travel duration is 2h 30m
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Sun Country Airlines15h 17m06:39 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center10:56 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Sun Country Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/7/2026 6:39:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/8/2026 10:56:00 AM. 50 Economy ticket for $288 per person are available. Travel duration is 15h 17m
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Alaska Airlines19h 44m09:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center5:44 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Alaska Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/7/2026 9:00:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/8/2026 5:44:00 AM. 50 Economy ticket for $344 per person are available. Travel duration is 19h 44m
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Frontier Airlines24h 49m06:00 AMChicago Midway AirportChicago Midway Airport7:49 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 6/7/2026 6:00:00 AM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/8/2026 7:49:00 AM. 50 Economy ticket for $229 per person are available. Travel duration is 24h 49m
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FlixBus22h 35m012:25 PMChicagoDowntown Bus Station12:00 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/7/2026 12:25:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/8/2026 12:00:00 PM. 50 Economy ticket for $112 per person are available. Travel duration is 22h 35m
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Greyhound US23h 25m06:00 PMChicagoDowntown Bus Station6:25 PMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/7/2026 6:00:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/8/2026 6:25:00 PM. 50 Economy ticket for $110 per person are available. Travel duration is 23h 25m
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Greyhound US23h 25m06:00 PMChicagoDowntown Bus Station6:25 PMBoston, MASouth Station0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/7/2026 6:00:00 PM to South Station, Boston, MA (USA) arriving at 6/8/2026 6:25:00 PM. 50 Economy ticket for $111 per person are available. Travel duration is 23h 25m
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FlixBus23h 55m011:05 AMChicago95th Red Line Station12:00 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 6/7/2026 11:05:00 AM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/8/2026 12:00:00 PM. 50 Economy ticket for $111 per person are available. Travel duration is 23h 55m
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Greyhound US27h 25m07:00 AMChicagoDowntown Bus Station11:25 AMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/7/2026 7:00:00 AM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/8/2026 11:25:00 AM. 50 Economy ticket for $112 per person are available. Travel duration is 27h 25m
Fastest Flights Sunday
Fastest Buses Sunday
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JetBlue Airways2h 29m08:30 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center11:59 PMBoston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/8/2026 8:30:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/8/2026 11:59:00 PM. 50 Economy ticket for $111 per person are available. Travel duration is 2h 29m
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United Airlines2h 33m09:41 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center1:14 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/8/2026 9:41:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/9/2026 1:14:00 AM. 50 Economy ticket for $97 per person are available. Travel duration is 2h 33m
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Sun Country Airlines14h 29m07:09 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center10:38 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Sun Country Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/8/2026 7:09:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/9/2026 10:38:00 AM. 50 Economy ticket for $295 per person are available. Travel duration is 14h 29m
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Alaska Airlines14h 34m02:10 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center5:44 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Alaska Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 6/8/2026 2:10:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/9/2026 5:44:00 AM. 50 Economy ticket for $343 per person are available. Travel duration is 14h 34m
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Frontier Airlines18h 48m012:04 PMChicago Midway AirportChicago Midway Airport7:52 AMBoston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 6/8/2026 12:04:00 PM to Boston Logan Airport, Boston Logan Airport (USA) arriving at 6/9/2026 7:52:00 AM. 50 Economy ticket for $159 per person are available. Travel duration is 18h 48m
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Greyhound US23h 25m06:00 PMChicagoDowntown Bus Station6:25 PMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/8/2026 6:00:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/9/2026 6:25:00 PM. 50 Economy ticket for $102 per person are available. Travel duration is 23h 25m
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FlixBus25h 35m07:15 PMChicagoDowntown Bus Station9:50 PMBoston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/8/2026 7:15:00 PM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/9/2026 9:50:00 PM. 50 Economy ticket for $104 per person are available. Travel duration is 25h 35m
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FlixBus25h 35m07:15 PMChicagoDowntown Bus Station9:50 PMBoston, MASouth Station0EconomyA Bus from FlixBus goes from Downtown Bus Station, Chicago (USA) at 6/8/2026 7:15:00 PM to South Station, Boston, MA (USA) arriving at 6/9/2026 9:50:00 PM. 50 Economy ticket for $105 per person are available. Travel duration is 25h 35m
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Greyhound US27h 25m07:00 AMChicagoDowntown Bus Station11:25 AMBoston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/8/2026 7:00:00 AM to Atlantic and Beach St, Boston, MA (USA) arriving at 6/9/2026 11:25:00 AM. 50 Economy ticket for $102 per person are available. Travel duration is 27h 25m
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Greyhound US27h 25m07:00 AMChicagoDowntown Bus Station11:25 AMBoston, MASouth Station0EconomyA Bus from Greyhound US goes from Downtown Bus Station, Chicago (USA) at 6/8/2026 7:00:00 AM to South Station, Boston, MA (USA) arriving at 6/9/2026 11:25:00 AM. 50 Economy ticket for $104 per person are available. Travel duration is 27h 25m
Fastest Flights Monday
Fastest Buses Monday
Here you will find all operators and timetables for a
Bus from Chicago to Boston, MA
What are the most popular stations in Chicago and Boston, MA?
In Chicago, you will usually depart from California & 35th Street Bus Stop, Downtown Bus Station or 95th Red Line Station, while in Boston, MA you will be arriving at Atlantic and Beach St, Logan Office Center Bus Stop or South 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 Boston, MA from Chicago? With 10 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 Chicago and Boston, MA, you can pay as low as $81 with a Flight from Frontier 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 United Airlines: you will get to Boston, MA in just 2h 24m.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 Chicago and Boston, MA are Greyhound US, FlixBus and Frontier 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 Chicago and Boston, MA 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 Cicero, IL or to Boston Logan Airport, and look at flights from Chicago Midway Airport, and landing at Boston Logan 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 Chicago to Boston, MA?
The most popular companies between Chicago and Boston, MA, are Greyhound US, FlixBus and Frontier Airlines. Be sure to check their seat class offers and the amenities that they provide.
Bus companies: Greyhound US and FlixBus
Airlines: Frontier Airlines, United Airlines, JetBlue Airways and 4 more.
All you need to know when you travel from Chicago to Boston, MA
Check all information on comfort and services on all modes of transports from Chicago to Boston, MA. See which seat classes are available, and what amenities are other advantages offered by the operators on your journey.
FAQs about the trip from Chicago to Boston, MA
How can I reach Boston, MA from Chicago?
Every day, there are on average 10 connections between Flight and Bus, with which you can get to Boston, MA from Chicago.
How far is Boston, MA from Chicago?
The distance between Chicago and Boston, MA is 849.6 miles.
What is the most ecofriendly mode of transport between Chicago and Boston, MA?
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 Chicago to Boston, MA?
You can get to Boston, MA with just $81 by taking a Flight from Frontier Airlines.
What is the fastest way to get from Chicago to Boston, MA?
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 Boston, MA in just 2h 24m with a Flight from United Airlines.
More routes to Chicago and to Boston, MA
Looking for more options? Here you can see the most popular routes to Chicago and to Boston, MA. Simply click on a connection, and you’ll find all the details about the route!
