What is the best way to travel from San Diego to Chicago?
Looking for a trip? Compare all the available Flights and Buses for the journey to Chicago from San Diego. 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 San Diego?
You can get to Chicago with just $103 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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United Airlines4h 21m02:07 PMSan Diego AirportSan Diego Airport8:28 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/17/2026 2:07:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/17/2026 8:28:00 PM. 50 Economy ticket for $115 per person are available. Travel duration is 4h 21m
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Alaska Airlines4h 25m07:00 AMSan Diego AirportSan Diego Airport1:25 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/17/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/17/2026 1:25:00 PM. 50 Economy ticket for $115 per person are available. Travel duration is 4h 25m
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Frontier Airlines32h 23m02:01 PMSan Diego AirportSan Diego Airport12:24 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/17/2026 2:01:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/19/2026 12:24:00 AM. 50 Economy ticket for $153 per person are available. Travel duration is 32h 23m
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Viva Aerobus23h 23m09:37 AMTijuana AirportTijuana Airport11:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Viva Aerobus goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/17/2026 9:37:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/18/2026 11:00:00 AM. 50 Economy ticket for $163 per person are available. Travel duration is 23h 23m
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Volaris11h 25m04:27 PMTijuana AirportTijuana Airport5:52 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Volaris goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/17/2026 4:27:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/18/2026 5:52:00 AM. 50 Economy ticket for $182 per person are available. Travel duration is 11h 25m
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Frontier Airlines20h 16m02:01 PMSan Diego AirportSan Diego Airport12:17 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/17/2026 2:01:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/18/2026 12:17:00 PM. 50 Economy ticket for $273 per person are available. Travel duration is 20h 16m
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FlixBus51h 15m01:10 PMSan DiegoSeaport Village6:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Seaport Village, San Diego (USA) at 10/17/2026 1:10:00 PM to 95th Red Line Station, Chicago (USA) arriving at 10/19/2026 6:25:00 PM. 50 Economy ticket for $182 per person are available. Travel duration is 51h 15m
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FlixBus50h 50m01:35 PMSan DiegoLa Jolla Village6:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from La Jolla Village, San Diego (USA) at 10/17/2026 1:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 10/19/2026 6:25:00 PM. 50 Economy ticket for $182 per person are available. Travel duration is 50h 50m
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Greyhound US52h 40m011:45 AMSan DiegoOld Town Transit Center6:25 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Old Town Transit Center, San Diego (USA) at 10/17/2026 11:45:00 AM to 95th Red Line Station, Chicago (USA) arriving at 10/19/2026 6:25:00 PM. 50 Economy ticket for $182 per person are available. Travel duration is 52h 40m
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FlixBus55h 0m09:25 AMSan DiegoOld Town Transit Center6:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Old Town Transit Center, San Diego (USA) at 10/17/2026 9:25:00 AM to 95th Red Line Station, Chicago (USA) arriving at 10/19/2026 6:25:00 PM. 50 Economy ticket for $183 per person are available. Travel duration is 55h 0m
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Greyhound US55h 25m07:45 PMSan DiegoOld Town Transit Center5:10 AMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Old Town Transit Center, San Diego (USA) at 10/17/2026 7:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 10/20/2026 5:10:00 AM. 50 Economy ticket for $183 per person are available. Travel duration is 55h 25m
Cheapest Flights Saturday
Cheapest Buses Saturday
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FlixBus71h 40m09:25 AMSan DiegoOld Town Transit Center11:05 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Old Town Transit Center, San Diego (USA) at 10/18/2026 9:25:00 AM to 95th Red Line Station, Chicago (USA) arriving at 10/21/2026 11:05:00 AM. 50 Economy ticket for $159 per person are available. Travel duration is 71h 40m
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FlixBus64h 50m01:10 PMSan DiegoSeaport Village8:00 AMChicagoCanal & Van Buren0EconomyA Bus from FlixBus goes from Seaport Village, San Diego (USA) at 10/18/2026 1:10:00 PM to Canal & Van Buren, Chicago (USA) arriving at 10/21/2026 8:00:00 AM. 50 Economy ticket for $162 per person are available. Travel duration is 64h 50m
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Greyhound US54h 35m07:45 PMSan DiegoOld Town Transit Center4:20 AMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Old Town Transit Center, San Diego (USA) at 10/18/2026 7:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 10/21/2026 4:20:00 AM. 50 Economy ticket for $163 per person are available. Travel duration is 54h 35m
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Greyhound US58h 15m07:45 PMSan DiegoOld Town Transit Center8:00 AMChicagoCanal & Van Buren0EconomyA Bus from Greyhound US goes from Old Town Transit Center, San Diego (USA) at 10/18/2026 7:45:00 PM to Canal & Van Buren, Chicago (USA) arriving at 10/21/2026 8:00:00 AM. 50 Economy ticket for $168 per person are available. Travel duration is 58h 15m
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Alaska Airlines4h 25m07:00 AMSan Diego AirportSan Diego Airport1:25 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/18/2026 7:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/18/2026 1:25:00 PM. 50 Economy ticket for $169 per person are available. Travel duration is 4h 25m
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Alaska Airlines3h 50m010:40 PMSan Diego AirportSan Diego Airport4:30 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/18/2026 10:40:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/19/2026 4:30:00 AM. 50 Economy ticket for $169 per person are available. Travel duration is 3h 50m
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American Airlines4h 9m010:40 PMSan Diego AirportSan Diego Airport4:49 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from American Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/18/2026 10:40:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/19/2026 4:49:00 AM. 50 Economy ticket for $169 per person are available. Travel duration is 4h 9m
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Alaska Airlines20h 36m02:01 PMSan Diego AirportSan Diego Airport12:37 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/18/2026 2:01:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/19/2026 12:37:00 PM. 50 Economy ticket for $213 per person are available. Travel duration is 20h 36m
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United Airlines9h 15m01:40 PMMcClellan-Palomar AirportMcClellan-Palomar Airport12:55 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from McClellan-Palomar Airport, McClellan-Palomar Airport (USA) at 10/18/2026 1:40:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/19/2026 12:55:00 AM. 50 Economy ticket for $374 per person are available. Travel duration is 9h 15m
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United Airlines7h 16m07:25 AMMcClellan-Palomar AirportMcClellan-Palomar Airport4:41 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from McClellan-Palomar Airport, McClellan-Palomar Airport (USA) at 10/18/2026 7:25:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/18/2026 4:41:00 PM. 50 Economy ticket for $485 per person are available. Travel duration is 7h 16m
Cheapest Buses Sunday
Cheapest Flights Sunday
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Alaska Airlines4h 13m05:46 PMSan Diego AirportSan Diego Airport11:59 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/19/2026 5:46:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/19/2026 11:59:00 PM. 50 Economy ticket for $136 per person are available. Travel duration is 4h 13m
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United Airlines4h 4m04:55 PMSan Diego AirportSan Diego Airport10:59 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/19/2026 4:55:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/19/2026 10:59:00 PM. 50 Economy ticket for $138 per person are available. Travel duration is 4h 4m
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Frontier Airlines40h 1m08:34 PMSan Diego AirportSan Diego Airport2:35 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/19/2026 8:34:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/21/2026 2:35:00 PM. 50 Economy ticket for $147 per person are available. Travel duration is 40h 1m
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Frontier Airlines16h 1m08:34 PMSan Diego AirportSan Diego Airport2:35 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/19/2026 8:34:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/20/2026 2:35:00 PM. 50 Economy ticket for $148 per person are available. Travel duration is 16h 1m
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Frontier Airlines15h 59m06:25 AMSan Diego AirportSan Diego Airport12:24 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/19/2026 6:25:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/20/2026 12:24:00 AM. 50 Economy ticket for $156 per person are available. Travel duration is 15h 59m
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Viva Aerobus23h 23m09:37 AMTijuana AirportTijuana Airport11:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Viva Aerobus goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/19/2026 9:37:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/20/2026 11:00:00 AM. 50 Economy ticket for $164 per person are available. Travel duration is 23h 23m
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FlixBus64h 20m010:05 PMSan DiegoOld Town Transit Center4:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Old Town Transit Center, San Diego (USA) at 10/19/2026 10:05:00 PM to Downtown Bus Station, Chicago (USA) arriving at 10/22/2026 4:25:00 PM. 50 Economy ticket for $163 per person are available. Travel duration is 64h 20m
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FlixBus64h 40m09:45 PMSan DiegoSeaport Village4:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Seaport Village, San Diego (USA) at 10/19/2026 9:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 10/22/2026 4:25:00 PM. 50 Economy ticket for $163 per person are available. Travel duration is 64h 40m
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FlixBus79h 55m010:05 PMSan DiegoOld Town Transit Center8:00 AMChicagoCanal & Van Buren0EconomyA Bus from FlixBus goes from Old Town Transit Center, San Diego (USA) at 10/19/2026 10:05:00 PM to Canal & Van Buren, Chicago (USA) arriving at 10/23/2026 8:00:00 AM. 50 Economy ticket for $164 per person are available. Travel duration is 79h 55m
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Greyhound US54h 35m07:45 PMSan DiegoOld Town Transit Center4:20 AMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Old Town Transit Center, San Diego (USA) at 10/19/2026 7:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 10/22/2026 4:20:00 AM. 50 Economy ticket for $165 per person are available. Travel duration is 54h 35m
Cheapest Flights Monday
Cheapest Buses Monday
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Greyhound US51h 55m010:30 AMTijuana AirportTijuana Airport4:25 PMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/20/2026 10:30:00 AM to Downtown Bus Station, Chicago (USA) arriving at 10/22/2026 4:25:00 PM. 50 Economy ticket for $176 per person are available. Travel duration is 51h 55m
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Greyhound US50h 40m011:45 AMSan DiegoOld Town Transit Center4:25 PMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Old Town Transit Center, San Diego (USA) at 10/20/2026 11:45:00 AM to Downtown Bus Station, Chicago (USA) arriving at 10/22/2026 4:25:00 PM. 50 Economy ticket for $184 per person are available. Travel duration is 50h 40m
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FlixBus49h 15m01:10 PMSan DiegoSeaport Village4:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Seaport Village, San Diego (USA) at 10/20/2026 1:10:00 PM to Downtown Bus Station, Chicago (USA) arriving at 10/22/2026 4:25:00 PM. 50 Economy ticket for $184 per person are available. Travel duration is 49h 15m
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FlixBus53h 0m09:25 AMSan DiegoOld Town Transit Center4:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Old Town Transit Center, San Diego (USA) at 10/20/2026 9:25:00 AM to Downtown Bus Station, Chicago (USA) arriving at 10/22/2026 4:25:00 PM. 50 Economy ticket for $185 per person are available. Travel duration is 53h 0m
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FlixBus64h 50m01:10 PMSan DiegoSeaport Village8:00 AMChicagoCanal & Van Buren0EconomyA Bus from FlixBus goes from Seaport Village, San Diego (USA) at 10/20/2026 1:10:00 PM to Canal & Van Buren, Chicago (USA) arriving at 10/23/2026 8:00:00 AM. 50 Economy ticket for $185 per person are available. Travel duration is 64h 50m
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Frontier Airlines19h 42m04:53 PMSan Diego AirportSan Diego Airport2:35 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/20/2026 4:53:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/21/2026 2:35:00 PM. 50 Economy ticket for $201 per person are available. Travel duration is 19h 42m
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Alaska Airlines18h 45m05:50 PMSan Diego AirportSan Diego Airport2:35 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/20/2026 5:50:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/21/2026 2:35:00 PM. 50 Economy ticket for $238 per person are available. Travel duration is 18h 45m
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Aeroméxico19h 26m01:07 AMTijuana AirportTijuana Airport10:33 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Aeroméxico goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/20/2026 1:07:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/20/2026 10:33:00 PM. 50 Economy ticket for $274 per person are available. Travel duration is 19h 26m
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Volaris11h 4m01:00 AMTijuana AirportTijuana Airport2:04 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Volaris goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/20/2026 1:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/20/2026 2:04:00 PM. 50 Economy ticket for $279 per person are available. Travel duration is 11h 4m
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Viva Aerobus39h 10m07:07 PMTijuana AirportTijuana Airport12:17 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Viva Aerobus goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/20/2026 7:07:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/22/2026 12:17:00 PM. 50 Economy ticket for $316 per person are available. Travel duration is 39h 10m
Cheapest Buses Tuesday
Cheapest Flights Tuesday
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Frontier Airlines13h 20m03:14 PMSan Diego AirportSan Diego Airport6:34 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/21/2026 3:14:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/22/2026 6:34:00 AM. 50 Economy ticket for $103 per person are available. Travel duration is 13h 20m
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United Airlines4h 21m06:40 AMSan Diego AirportSan Diego Airport1:01 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/21/2026 6:40:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/21/2026 1:01:00 PM. 50 Economy ticket for $127 per person are available. Travel duration is 4h 21m
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Alaska Airlines4h 25m07:00 AMSan Diego AirportSan Diego Airport1:25 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/21/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/21/2026 1:25:00 PM. 50 Economy ticket for $127 per person are available. Travel duration is 4h 25m
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Viva Aerobus15h 59m06:00 AMTijuana AirportTijuana Airport11:59 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Viva Aerobus goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/21/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/21/2026 11:59:00 PM. 50 Economy ticket for $169 per person are available. Travel duration is 15h 59m
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Volaris8h 30m05:45 PMTijuana AirportTijuana Airport4:15 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Volaris goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/21/2026 5:45:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/22/2026 4:15:00 AM. 50 Economy ticket for $174 per person are available. Travel duration is 8h 30m
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FlixBus51h 15m01:10 PMSan DiegoSeaport Village6:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Seaport Village, San Diego (USA) at 10/21/2026 1:10:00 PM to 95th Red Line Station, Chicago (USA) arriving at 10/23/2026 6:25:00 PM. 50 Economy ticket for $123 per person are available. Travel duration is 51h 15m
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Greyhound US55h 35m07:45 PMSan DiegoOld Town Transit Center5:20 AMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Old Town Transit Center, San Diego (USA) at 10/21/2026 7:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 10/24/2026 5:20:00 AM. 50 Economy ticket for $125 per person are available. Travel duration is 55h 35m
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FlixBus55h 0m09:25 AMSan DiegoOld Town Transit Center6:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Old Town Transit Center, San Diego (USA) at 10/21/2026 9:25:00 AM to 95th Red Line Station, Chicago (USA) arriving at 10/23/2026 6:25:00 PM. 50 Economy ticket for $125 per person are available. Travel duration is 55h 0m
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Greyhound US54h 35m09:50 AMSan DiegoOld Town Transit Center6:25 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Old Town Transit Center, San Diego (USA) at 10/21/2026 9:50:00 AM to 95th Red Line Station, Chicago (USA) arriving at 10/23/2026 6:25:00 PM. 50 Economy ticket for $139 per person are available. Travel duration is 54h 35m
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FlixBus49h 15m01:10 PMSan DiegoSeaport Village4:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Seaport Village, San Diego (USA) at 10/21/2026 1:10:00 PM to Downtown Bus Station, Chicago (USA) arriving at 10/23/2026 4:25:00 PM. 50 Economy ticket for $142 per person are available. Travel duration is 49h 15m
Cheapest Flights Wednesday
Cheapest Buses Wednesday
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Frontier Airlines8h 58m02:01 PMSan Diego AirportSan Diego Airport12:59 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/22/2026 2:01:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/23/2026 12:59:00 AM. 50 Economy ticket for $116 per person are available. Travel duration is 8h 58m
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Alaska Airlines4h 13m05:46 PMSan Diego AirportSan Diego Airport11:59 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/22/2026 5:46:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/22/2026 11:59:00 PM. 50 Economy ticket for $137 per person are available. Travel duration is 4h 13m
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United Airlines4h 21m02:07 PMSan Diego AirportSan Diego Airport8:28 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/22/2026 2:07:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/22/2026 8:28:00 PM. 50 Economy ticket for $137 per person are available. Travel duration is 4h 21m
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Viva Aerobus23h 23m09:37 AMTijuana AirportTijuana Airport11:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Viva Aerobus goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/22/2026 9:37:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/23/2026 11:00:00 AM. 50 Economy ticket for $168 per person are available. Travel duration is 23h 23m
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Volaris9h 9m05:45 PMTijuana AirportTijuana Airport4:54 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Volaris goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/22/2026 5:45:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/23/2026 4:54:00 AM. 50 Economy ticket for $200 per person are available. Travel duration is 9h 9m
Cheapest Flights Thursday
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Frontier Airlines8h 58m02:01 PMSan Diego AirportSan Diego Airport12:59 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/23/2026 2:01:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/24/2026 12:59:00 AM. 50 Economy ticket for $142 per person are available. Travel duration is 8h 58m
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Alaska Airlines4h 18m012:35 PMSan Diego AirportSan Diego Airport6:53 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/23/2026 12:35:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/23/2026 6:53:00 PM. 50 Economy ticket for $146 per person are available. Travel duration is 4h 18m
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Alaska Airlines4h 13m05:46 PMSan Diego AirportSan Diego Airport11:59 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/23/2026 5:46:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/23/2026 11:59:00 PM. 50 Economy ticket for $146 per person are available. Travel duration is 4h 13m
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United Airlines4h 21m02:07 PMSan Diego AirportSan Diego Airport8:28 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/23/2026 2:07:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/23/2026 8:28:00 PM. 50 Economy ticket for $148 per person are available. Travel duration is 4h 21m
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United Airlines4h 4m04:55 PMSan Diego AirportSan Diego Airport10:59 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/23/2026 4:55:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/23/2026 10:59:00 PM. 50 Economy ticket for $148 per person are available. Travel duration is 4h 4m
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Greyhound US50h 40m011:45 AMSan DiegoOld Town Transit Center4:25 PMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Old Town Transit Center, San Diego (USA) at 10/23/2026 11:45:00 AM to Downtown Bus Station, Chicago (USA) arriving at 10/25/2026 4:25:00 PM. 50 Economy ticket for $189 per person are available. Travel duration is 50h 40m
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FlixBus49h 15m01:10 PMSan DiegoSeaport Village4:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Seaport Village, San Diego (USA) at 10/23/2026 1:10:00 PM to Downtown Bus Station, Chicago (USA) arriving at 10/25/2026 4:25:00 PM. 50 Economy ticket for $189 per person are available. Travel duration is 49h 15m
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FlixBus53h 0m09:25 AMSan DiegoOld Town Transit Center4:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Old Town Transit Center, San Diego (USA) at 10/23/2026 9:25:00 AM to Downtown Bus Station, Chicago (USA) arriving at 10/25/2026 4:25:00 PM. 50 Economy ticket for $190 per person are available. Travel duration is 53h 0m
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FlixBus63h 50m010:35 PMSan DiegoOld Town Transit Center4:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Old Town Transit Center, San Diego (USA) at 10/23/2026 10:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 10/26/2026 4:25:00 PM. 50 Economy ticket for $190 per person are available. Travel duration is 63h 50m
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Greyhound US51h 55m010:30 AMTijuana AirportTijuana Airport4:25 PMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/23/2026 10:30:00 AM to Downtown Bus Station, Chicago (USA) arriving at 10/25/2026 4:25:00 PM. 50 Economy ticket for $191 per person are available. Travel duration is 51h 55m
Cheapest Flights Friday
Cheapest Buses Friday
What are the fastest trips from San Diego to Chicago?
You can get to Chicago from San Diego in just 3h 50m with a Flight from Alaska 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 Airlines4h 21m02:07 PMSan Diego AirportSan Diego Airport8:28 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/17/2026 2:07:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/17/2026 8:28:00 PM. 50 Economy ticket for $115 per person are available. Travel duration is 4h 21m
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Alaska Airlines4h 25m07:00 AMSan Diego AirportSan Diego Airport1:25 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/17/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/17/2026 1:25:00 PM. 50 Economy ticket for $115 per person are available. Travel duration is 4h 25m
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Volaris11h 25m04:27 PMTijuana AirportTijuana Airport5:52 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Volaris goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/17/2026 4:27:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/18/2026 5:52:00 AM. 50 Economy ticket for $182 per person are available. Travel duration is 11h 25m
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Frontier Airlines15h 18m06:25 AMSan Diego AirportSan Diego Airport11:43 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/17/2026 6:25:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/17/2026 11:43:00 PM. 50 Economy ticket for $279 per person are available. Travel duration is 15h 18m
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JetBlue Airways18h 15m09:30 PMSan Diego AirportSan Diego Airport5:45 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from JetBlue Airways goes from San Diego Airport, San Diego Airport (USA) at 10/17/2026 9:30:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/18/2026 5:45:00 PM. 50 Economy ticket for $760 per person are available. Travel duration is 18h 15m
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Westjet Airlines19h 42m01:18 PMSan Diego AirportSan Diego Airport11:00 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/17/2026 1:18:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/18/2026 11:00:00 AM. 50 Economy ticket for $1,112 per person are available. Travel duration is 19h 42m
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FlixBus50h 50m01:35 PMSan DiegoLa Jolla Village6:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from La Jolla Village, San Diego (USA) at 10/17/2026 1:35:00 PM to 95th Red Line Station, Chicago (USA) arriving at 10/19/2026 6:25:00 PM. 50 Economy ticket for $182 per person are available. Travel duration is 50h 50m
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FlixBus51h 15m01:10 PMSan DiegoSeaport Village6:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Seaport Village, San Diego (USA) at 10/17/2026 1:10:00 PM to 95th Red Line Station, Chicago (USA) arriving at 10/19/2026 6:25:00 PM. 50 Economy ticket for $182 per person are available. Travel duration is 51h 15m
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Greyhound US52h 40m011:45 AMSan DiegoOld Town Transit Center6:25 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Old Town Transit Center, San Diego (USA) at 10/17/2026 11:45:00 AM to 95th Red Line Station, Chicago (USA) arriving at 10/19/2026 6:25:00 PM. 50 Economy ticket for $182 per person are available. Travel duration is 52h 40m
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FlixBus55h 0m09:25 AMSan DiegoOld Town Transit Center6:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Old Town Transit Center, San Diego (USA) at 10/17/2026 9:25:00 AM to 95th Red Line Station, Chicago (USA) arriving at 10/19/2026 6:25:00 PM. 50 Economy ticket for $183 per person are available. Travel duration is 55h 0m
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Greyhound US55h 25m07:45 PMSan DiegoOld Town Transit Center5:10 AMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Old Town Transit Center, San Diego (USA) at 10/17/2026 7:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 10/20/2026 5:10:00 AM. 50 Economy ticket for $183 per person are available. Travel duration is 55h 25m
Fastest Flights Saturday
Fastest Buses Saturday
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Alaska Airlines3h 50m010:40 PMSan Diego AirportSan Diego Airport4:30 AMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/18/2026 10:40:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/19/2026 4:30:00 AM. 50 Economy ticket for $169 per person are available. Travel duration is 3h 50m
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American Airlines4h 9m010:40 PMSan Diego AirportSan Diego Airport4:49 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from American Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/18/2026 10:40:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/19/2026 4:49:00 AM. 50 Economy ticket for $169 per person are available. Travel duration is 4h 9m
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Alaska Airlines4h 25m07:00 AMSan Diego AirportSan Diego Airport1:25 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/18/2026 7:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/18/2026 1:25:00 PM. 50 Economy ticket for $169 per person are available. Travel duration is 4h 25m
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United Airlines7h 16m07:25 AMMcClellan-Palomar AirportMcClellan-Palomar Airport4:41 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from McClellan-Palomar Airport, McClellan-Palomar Airport (USA) at 10/18/2026 7:25:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/18/2026 4:41:00 PM. 50 Economy ticket for $485 per person are available. Travel duration is 7h 16m
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United Airlines8h 55m01:04 PMMcClellan-Palomar AirportMcClellan-Palomar Airport11:59 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from McClellan-Palomar Airport, McClellan-Palomar Airport (USA) at 10/18/2026 1:04:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/18/2026 11:59:00 PM. 50 Economy ticket for $485 per person are available. Travel duration is 8h 55m
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United Airlines9h 15m01:40 PMMcClellan-Palomar AirportMcClellan-Palomar Airport12:55 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from McClellan-Palomar Airport, McClellan-Palomar Airport (USA) at 10/18/2026 1:40:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/19/2026 12:55:00 AM. 50 Economy ticket for $374 per person are available. Travel duration is 9h 15m
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Greyhound US54h 35m07:45 PMSan DiegoOld Town Transit Center4:20 AMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Old Town Transit Center, San Diego (USA) at 10/18/2026 7:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 10/21/2026 4:20:00 AM. 50 Economy ticket for $163 per person are available. Travel duration is 54h 35m
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Greyhound US58h 15m07:45 PMSan DiegoOld Town Transit Center8:00 AMChicagoCanal & Van Buren0EconomyA Bus from Greyhound US goes from Old Town Transit Center, San Diego (USA) at 10/18/2026 7:45:00 PM to Canal & Van Buren, Chicago (USA) arriving at 10/21/2026 8:00:00 AM. 50 Economy ticket for $168 per person are available. Travel duration is 58h 15m
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FlixBus64h 50m01:10 PMSan DiegoSeaport Village8:00 AMChicagoCanal & Van Buren0EconomyA Bus from FlixBus goes from Seaport Village, San Diego (USA) at 10/18/2026 1:10:00 PM to Canal & Van Buren, Chicago (USA) arriving at 10/21/2026 8:00:00 AM. 50 Economy ticket for $162 per person are available. Travel duration is 64h 50m
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FlixBus71h 40m09:25 AMSan DiegoOld Town Transit Center11:05 AMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Old Town Transit Center, San Diego (USA) at 10/18/2026 9:25:00 AM to 95th Red Line Station, Chicago (USA) arriving at 10/21/2026 11:05:00 AM. 50 Economy ticket for $159 per person are available. Travel duration is 71h 40m
Fastest Flights Sunday
Fastest Buses Sunday
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United Airlines4h 4m04:55 PMSan Diego AirportSan Diego Airport10:59 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/19/2026 4:55:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/19/2026 10:59:00 PM. 50 Economy ticket for $138 per person are available. Travel duration is 4h 4m
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Alaska Airlines4h 13m05:46 PMSan Diego AirportSan Diego Airport11:59 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/19/2026 5:46:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/19/2026 11:59:00 PM. 50 Economy ticket for $136 per person are available. Travel duration is 4h 13m
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Westjet Airlines14h 35m010:00 PMSan Diego AirportSan Diego Airport2:35 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Westjet Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/19/2026 10:00:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/20/2026 2:35:00 PM. 50 Economy ticket for $761 per person are available. Travel duration is 14h 35m
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Frontier Airlines15h 59m06:25 AMSan Diego AirportSan Diego Airport12:24 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/19/2026 6:25:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/20/2026 12:24:00 AM. 50 Economy ticket for $156 per person are available. Travel duration is 15h 59m
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Frontier Airlines16h 1m08:34 PMSan Diego AirportSan Diego Airport2:35 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/19/2026 8:34:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/20/2026 2:35:00 PM. 50 Economy ticket for $148 per person are available. Travel duration is 16h 1m
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Viva Aerobus23h 23m09:37 AMTijuana AirportTijuana Airport11:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Viva Aerobus goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/19/2026 9:37:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/20/2026 11:00:00 AM. 50 Economy ticket for $164 per person are available. Travel duration is 23h 23m
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Greyhound US54h 35m07:45 PMSan DiegoOld Town Transit Center4:20 AMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Old Town Transit Center, San Diego (USA) at 10/19/2026 7:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 10/22/2026 4:20:00 AM. 50 Economy ticket for $165 per person are available. Travel duration is 54h 35m
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FlixBus64h 20m010:05 PMSan DiegoOld Town Transit Center4:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Old Town Transit Center, San Diego (USA) at 10/19/2026 10:05:00 PM to Downtown Bus Station, Chicago (USA) arriving at 10/22/2026 4:25:00 PM. 50 Economy ticket for $163 per person are available. Travel duration is 64h 20m
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FlixBus64h 40m09:45 PMSan DiegoSeaport Village4:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Seaport Village, San Diego (USA) at 10/19/2026 9:45:00 PM to Downtown Bus Station, Chicago (USA) arriving at 10/22/2026 4:25:00 PM. 50 Economy ticket for $163 per person are available. Travel duration is 64h 40m
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FlixBus79h 55m010:05 PMSan DiegoOld Town Transit Center8:00 AMChicagoCanal & Van Buren0EconomyA Bus from FlixBus goes from Old Town Transit Center, San Diego (USA) at 10/19/2026 10:05:00 PM to Canal & Van Buren, Chicago (USA) arriving at 10/23/2026 8:00:00 AM. 50 Economy ticket for $164 per person are available. Travel duration is 79h 55m
Fastest Flights Monday
Fastest Buses Monday
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Volaris11h 4m01:00 AMTijuana AirportTijuana Airport2:04 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Volaris goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/20/2026 1:00:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/20/2026 2:04:00 PM. 50 Economy ticket for $279 per person are available. Travel duration is 11h 4m
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Alaska Airlines18h 45m05:50 PMSan Diego AirportSan Diego Airport2:35 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/20/2026 5:50:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/21/2026 2:35:00 PM. 50 Economy ticket for $238 per person are available. Travel duration is 18h 45m
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Aeroméxico19h 26m01:07 AMTijuana AirportTijuana Airport10:33 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Aeroméxico goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/20/2026 1:07:00 AM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/20/2026 10:33:00 PM. 50 Economy ticket for $274 per person are available. Travel duration is 19h 26m
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Frontier Airlines19h 42m04:53 PMSan Diego AirportSan Diego Airport2:35 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/20/2026 4:53:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/21/2026 2:35:00 PM. 50 Economy ticket for $201 per person are available. Travel duration is 19h 42m
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Viva Aerobus39h 10m07:07 PMTijuana AirportTijuana Airport12:17 PMChicago Midway AirportChicago Midway Airport0EconomyA Flight from Viva Aerobus goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/20/2026 7:07:00 PM to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 10/22/2026 12:17:00 PM. 50 Economy ticket for $316 per person are available. Travel duration is 39h 10m
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FlixBus49h 15m01:10 PMSan DiegoSeaport Village4:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Seaport Village, San Diego (USA) at 10/20/2026 1:10:00 PM to Downtown Bus Station, Chicago (USA) arriving at 10/22/2026 4:25:00 PM. 50 Economy ticket for $184 per person are available. Travel duration is 49h 15m
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Greyhound US50h 40m011:45 AMSan DiegoOld Town Transit Center4:25 PMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Old Town Transit Center, San Diego (USA) at 10/20/2026 11:45:00 AM to Downtown Bus Station, Chicago (USA) arriving at 10/22/2026 4:25:00 PM. 50 Economy ticket for $184 per person are available. Travel duration is 50h 40m
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Greyhound US51h 55m010:30 AMTijuana AirportTijuana Airport4:25 PMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/20/2026 10:30:00 AM to Downtown Bus Station, Chicago (USA) arriving at 10/22/2026 4:25:00 PM. 50 Economy ticket for $176 per person are available. Travel duration is 51h 55m
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FlixBus53h 0m09:25 AMSan DiegoOld Town Transit Center4:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Old Town Transit Center, San Diego (USA) at 10/20/2026 9:25:00 AM to Downtown Bus Station, Chicago (USA) arriving at 10/22/2026 4:25:00 PM. 50 Economy ticket for $185 per person are available. Travel duration is 53h 0m
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FlixBus64h 50m01:10 PMSan DiegoSeaport Village8:00 AMChicagoCanal & Van Buren0EconomyA Bus from FlixBus goes from Seaport Village, San Diego (USA) at 10/20/2026 1:10:00 PM to Canal & Van Buren, Chicago (USA) arriving at 10/23/2026 8:00:00 AM. 50 Economy ticket for $185 per person are available. Travel duration is 64h 50m
Fastest Flights Tuesday
Fastest Buses Tuesday
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United Airlines4h 21m06:40 AMSan Diego AirportSan Diego Airport1:01 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/21/2026 6:40:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/21/2026 1:01:00 PM. 50 Economy ticket for $127 per person are available. Travel duration is 4h 21m
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Alaska Airlines4h 25m07:00 AMSan Diego AirportSan Diego Airport1:25 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/21/2026 7:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/21/2026 1:25:00 PM. 50 Economy ticket for $127 per person are available. Travel duration is 4h 25m
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Volaris8h 30m05:45 PMTijuana AirportTijuana Airport4:15 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Volaris goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/21/2026 5:45:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/22/2026 4:15:00 AM. 50 Economy ticket for $174 per person are available. Travel duration is 8h 30m
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Frontier Airlines13h 20m03:14 PMSan Diego AirportSan Diego Airport6:34 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/21/2026 3:14:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/22/2026 6:34:00 AM. 50 Economy ticket for $103 per person are available. Travel duration is 13h 20m
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Viva Aerobus15h 59m06:00 AMTijuana AirportTijuana Airport11:59 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Viva Aerobus goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/21/2026 6:00:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/21/2026 11:59:00 PM. 50 Economy ticket for $169 per person are available. Travel duration is 15h 59m
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FlixBus49h 15m01:10 PMSan DiegoSeaport Village4:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Seaport Village, San Diego (USA) at 10/21/2026 1:10:00 PM to Downtown Bus Station, Chicago (USA) arriving at 10/23/2026 4:25:00 PM. 50 Economy ticket for $142 per person are available. Travel duration is 49h 15m
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FlixBus51h 15m01:10 PMSan DiegoSeaport Village6:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Seaport Village, San Diego (USA) at 10/21/2026 1:10:00 PM to 95th Red Line Station, Chicago (USA) arriving at 10/23/2026 6:25:00 PM. 50 Economy ticket for $123 per person are available. Travel duration is 51h 15m
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Greyhound US54h 35m09:50 AMSan DiegoOld Town Transit Center6:25 PMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Old Town Transit Center, San Diego (USA) at 10/21/2026 9:50:00 AM to 95th Red Line Station, Chicago (USA) arriving at 10/23/2026 6:25:00 PM. 50 Economy ticket for $139 per person are available. Travel duration is 54h 35m
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FlixBus55h 0m09:25 AMSan DiegoOld Town Transit Center6:25 PMChicago95th Red Line Station0EconomyA Bus from FlixBus goes from Old Town Transit Center, San Diego (USA) at 10/21/2026 9:25:00 AM to 95th Red Line Station, Chicago (USA) arriving at 10/23/2026 6:25:00 PM. 50 Economy ticket for $125 per person are available. Travel duration is 55h 0m
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Greyhound US55h 35m07:45 PMSan DiegoOld Town Transit Center5:20 AMChicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Old Town Transit Center, San Diego (USA) at 10/21/2026 7:45:00 PM to 95th Red Line Station, Chicago (USA) arriving at 10/24/2026 5:20:00 AM. 50 Economy ticket for $125 per person are available. Travel duration is 55h 35m
Fastest Flights Wednesday
Fastest Buses Wednesday
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Alaska Airlines4h 13m05:46 PMSan Diego AirportSan Diego Airport11:59 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/22/2026 5:46:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/22/2026 11:59:00 PM. 50 Economy ticket for $137 per person are available. Travel duration is 4h 13m
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United Airlines4h 21m02:07 PMSan Diego AirportSan Diego Airport8:28 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/22/2026 2:07:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/22/2026 8:28:00 PM. 50 Economy ticket for $137 per person are available. Travel duration is 4h 21m
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Frontier Airlines8h 58m02:01 PMSan Diego AirportSan Diego Airport12:59 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/22/2026 2:01:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/23/2026 12:59:00 AM. 50 Economy ticket for $116 per person are available. Travel duration is 8h 58m
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Volaris9h 9m05:45 PMTijuana AirportTijuana Airport4:54 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Volaris goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/22/2026 5:45:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/23/2026 4:54:00 AM. 50 Economy ticket for $200 per person are available. Travel duration is 9h 9m
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Viva Aerobus23h 23m09:37 AMTijuana AirportTijuana Airport11:00 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Viva Aerobus goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/22/2026 9:37:00 AM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/23/2026 11:00:00 AM. 50 Economy ticket for $168 per person are available. Travel duration is 23h 23m
Fastest Flights Thursday
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United Airlines4h 4m04:55 PMSan Diego AirportSan Diego Airport10:59 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/23/2026 4:55:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/23/2026 10:59:00 PM. 50 Economy ticket for $148 per person are available. Travel duration is 4h 4m
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Alaska Airlines4h 13m05:46 PMSan Diego AirportSan Diego Airport11:59 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/23/2026 5:46:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/23/2026 11:59:00 PM. 50 Economy ticket for $146 per person are available. Travel duration is 4h 13m
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Alaska Airlines4h 18m012:35 PMSan Diego AirportSan Diego Airport6:53 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Alaska Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/23/2026 12:35:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/23/2026 6:53:00 PM. 50 Economy ticket for $146 per person are available. Travel duration is 4h 18m
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United Airlines4h 21m02:07 PMSan Diego AirportSan Diego Airport8:28 PMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/23/2026 2:07:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/23/2026 8:28:00 PM. 50 Economy ticket for $148 per person are available. Travel duration is 4h 21m
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Frontier Airlines8h 58m02:01 PMSan Diego AirportSan Diego Airport12:59 AMChicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from San Diego Airport, San Diego Airport (USA) at 10/23/2026 2:01:00 PM to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 10/24/2026 12:59:00 AM. 50 Economy ticket for $142 per person are available. Travel duration is 8h 58m
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FlixBus49h 15m01:10 PMSan DiegoSeaport Village4:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Seaport Village, San Diego (USA) at 10/23/2026 1:10:00 PM to Downtown Bus Station, Chicago (USA) arriving at 10/25/2026 4:25:00 PM. 50 Economy ticket for $189 per person are available. Travel duration is 49h 15m
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Greyhound US50h 40m011:45 AMSan DiegoOld Town Transit Center4:25 PMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Old Town Transit Center, San Diego (USA) at 10/23/2026 11:45:00 AM to Downtown Bus Station, Chicago (USA) arriving at 10/25/2026 4:25:00 PM. 50 Economy ticket for $189 per person are available. Travel duration is 50h 40m
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Greyhound US51h 55m010:30 AMTijuana AirportTijuana Airport4:25 PMChicagoDowntown Bus Station0EconomyA Bus from Greyhound US goes from Tijuana Airport, Tijuana Airport (Mexico) at 10/23/2026 10:30:00 AM to Downtown Bus Station, Chicago (USA) arriving at 10/25/2026 4:25:00 PM. 50 Economy ticket for $191 per person are available. Travel duration is 51h 55m
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FlixBus53h 0m09:25 AMSan DiegoOld Town Transit Center4:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Old Town Transit Center, San Diego (USA) at 10/23/2026 9:25:00 AM to Downtown Bus Station, Chicago (USA) arriving at 10/25/2026 4:25:00 PM. 50 Economy ticket for $190 per person are available. Travel duration is 53h 0m
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FlixBus63h 50m010:35 PMSan DiegoOld Town Transit Center4:25 PMChicagoDowntown Bus Station0EconomyA Bus from FlixBus goes from Old Town Transit Center, San Diego (USA) at 10/23/2026 10:35:00 PM to Downtown Bus Station, Chicago (USA) arriving at 10/26/2026 4:25:00 PM. 50 Economy ticket for $190 per person are available. Travel duration is 63h 50m
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Here you will find all operators and timetables for a
Bus from San Diego to Chicago
What are the most popular stations in San Diego and Chicago?
In San Diego, you will usually depart from San Ysidro Transit Center, Old Town Transit Center or Santa Fe Depot, 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 San Diego? With 11 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 San Diego and Chicago, you can pay as low as $103 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 Alaska Airlines: you will get to Chicago in just 3h 50m.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 San Diego and Chicago are FlixBus, Greyhound US and Alaska 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 San Diego 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 San Diego Airport or to Cicero, IL, and look at flights from Tijuana 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 San Diego to Chicago?
The most popular companies between San Diego and Chicago, are FlixBus, Greyhound US and Alaska Airlines. Be sure to check their seat class offers and the amenities that they provide.
Bus companies: FlixBus and Greyhound US
Airlines: Alaska Airlines, Frontier Airlines, United Airlines and 6 more.
All you need to know when you travel from San Diego to Chicago
Check all information on comfort and services on all modes of transports from San Diego 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 San Diego to Chicago
How can I reach Chicago from San Diego?
Every day, there are on average 11 connections between Flight and Bus, with which you can get to Chicago from San Diego.
How far is Chicago from San Diego?
The distance between San Diego and Chicago is 1,730.9 miles.
What is the most ecofriendly mode of transport between San Diego 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 75 kgs of CO2, a train 97 kgs, a car 474 kgs, and a flight 685 kgs.
What is the cheapest mode of transport from San Diego to Chicago?
You can get to Chicago with just $103 by taking a Flight from Frontier Airlines.
What is the fastest way to get from San Diego 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 3h 50m with a Flight from Alaska Airlines.
More routes to San Diego and to Chicago
Looking for more options? Here you can see the most popular routes to San Diego and to Chicago. Simply click on a connection, and you’ll find all the details about the route!
- Trips to San Diego
- Bakersfield, CA to San Diego
- Cedar City, UT to San Diego
- Chicago to San Diego
- Dallas to San Diego
- Denver to San Diego
- El Paso, TX to San Diego
- Las Vegas to San Diego
- Los Angeles to San Diego
- Mexico City to San Diego
- New York to San Diego
- Pasco, WA to San Diego
- Phoenix, AZ to San Diego
- Salt Lake City, UT to San Diego
- San Francisco to San Diego
- Seattle, WA to San Diego
- Tucson, AZ to San Diego
- Trips to Chicago
- Aguascalientes to Chicago
- Atlanta, GA to Chicago
- Cincinnati to Chicago
- Cleveland to Chicago
- Columbus, OH to Chicago
- Dallas to Chicago
- Durango, DG to Chicago
- El Paso, TX to Chicago
- Guadalajara, JC to Chicago
- Houston to Chicago
- Las Vegas to Chicago
- Los Angeles to Chicago
- McAllen, TX to Chicago
- Memphis to Chicago
- Mexico City to Chicago
- Nashville to Chicago
- New York to Chicago
- Phoenix, AZ to Chicago
- Pittsburgh to Chicago
- San Antonio, TX to Chicago
- San Luis Potosí to Chicago
- Toronto, ON to Chicago
