What is the best way to travel from Boston, MA to Chicago?
Looking for a trip? Check and compare all the available Flights and Buses to Chicago from Boston, MA. Look at different modes of transportation, search for the cheapest tickets, fastest rides and most popular stations, and see all 2 available companies to find your perfect trip!
What is the cheapest way to reach Chicago from Boston, MA?
You can reach Chicago with just £74 by taking a Flight from JetBlue Airways, but there are many more cheap offers: we have selected the best ones for you for the next few days here.
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FlixBus37h 30m021:50Boston, MAAtlantic and Beach St10:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 01/11/2026 21:50:00 to 95th Red Line Station, Chicago (USA) arriving at 03/11/2026 10:20:00. 50 Economy ticket for £144 per person are available. Travel duration is 37h 30m
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FlixBus37h 30m021:50Boston, MASouth Station10:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from South Station, Boston, MA (USA) at 01/11/2026 21:50:00 to 95th Red Line Station, Chicago (USA) arriving at 03/11/2026 10:20:00. 50 Economy ticket for £146 per person are available. Travel duration is 37h 30m
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FlixBus33h 20m021:50Boston, MAAtlantic and Beach St06:10ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 01/11/2026 21:50:00 to Downtown Coach Station, Chicago (USA) arriving at 03/11/2026 06:10:00. 50 Economy ticket for £154 per person are available. Travel duration is 33h 20m
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Greyhound US31h 45m016:45Boston, MASouth Station23:30Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from South Station, Boston, MA (USA) at 01/11/2026 16:45:00 to 95th Red Line Station, Chicago (USA) arriving at 02/11/2026 23:30:00. 50 Economy ticket for £175 per person are available. Travel duration is 31h 45m
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Greyhound US31h 45m016:45Boston, MAAtlantic and Beach St23:30Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 01/11/2026 16:45:00 to 95th Red Line Station, Chicago (USA) arriving at 02/11/2026 23:30:00. 50 Economy ticket for £177 per person are available. Travel duration is 31h 45m
Cheapest Buses Sunday
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JetBlue Airways3h 12m017:05Boston Logan AirportBoston Logan Airport19:17Chicago Midway AirportChicago Midway Airport0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 02/11/2026 17:05:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 02/11/2026 19:17:00. 50 Economy ticket for £74 per person are available. Travel duration is 3h 12m
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JetBlue Airways2h 45m018:30Boston Logan AirportBoston Logan Airport20:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 02/11/2026 18:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 02/11/2026 20:15:00. 50 Economy ticket for £125 per person are available. Travel duration is 2h 45m
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JetBlue Airways3h 1m009:59Boston Logan AirportBoston Logan Airport12:00Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 02/11/2026 09:59:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 02/11/2026 12:00:00. 50 Economy ticket for £126 per person are available. Travel duration is 3h 1m
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JetBlue Airways3h 12m017:05Boston Logan AirportBoston Logan Airport19:17Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 02/11/2026 17:05:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 02/11/2026 19:17:00. 50 Economy ticket for £126 per person are available. Travel duration is 3h 12m
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United Airlines3h 0m006:00Boston Logan AirportBoston Logan Airport08:00Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 02/11/2026 06:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 02/11/2026 08:00:00. 50 Economy ticket for £127 per person are available. Travel duration is 3h 0m
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United Airlines3h 3m007:31Boston Logan AirportBoston Logan Airport09:34Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 02/11/2026 07:31:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 02/11/2026 09:34:00. 50 Economy ticket for £127 per person are available. Travel duration is 3h 3m
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Greyhound US22h 30m012:30Boston, MAAtlantic and Beach St10:00ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 02/11/2026 12:30:00 to Downtown Coach Station, Chicago (USA) arriving at 03/11/2026 10:00:00. 50 Economy ticket for £100 per person are available. Travel duration is 22h 30m
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Greyhound US28h 20m016:45Boston, MAAtlantic and Beach St20:05ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 02/11/2026 16:45:00 to Downtown Coach Station, Chicago (USA) arriving at 03/11/2026 20:05:00. 50 Economy ticket for £100 per person are available. Travel duration is 28h 20m
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Greyhound US25h 10m006:00Boston, MAAtlantic and Beach St06:10ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 02/11/2026 06:00:00 to Downtown Coach Station, Chicago (USA) arriving at 03/11/2026 06:10:00. 50 Economy ticket for £103 per person are available. Travel duration is 25h 10m
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FlixBus27h 50m017:15Boston, MAAtlantic and Beach St20:05ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 02/11/2026 17:15:00 to Downtown Coach Station, Chicago (USA) arriving at 03/11/2026 20:05:00. 50 Economy ticket for £108 per person are available. Travel duration is 27h 50m
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FlixBus27h 50m017:15Boston, MASouth Station20:05ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from South Station, Boston, MA (USA) at 02/11/2026 17:15:00 to Downtown Coach Station, Chicago (USA) arriving at 03/11/2026 20:05:00. 50 Economy ticket for £111 per person are available. Travel duration is 27h 50m
Cheapest Flights Monday
Cheapest Buses Monday
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JetBlue Airways3h 1m009:59Boston Logan AirportBoston Logan Airport12:00Chicago Midway AirportChicago Midway Airport0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 03/11/2026 09:59:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 03/11/2026 12:00:00. 50 Economy ticket for £74 per person are available. Travel duration is 3h 1m
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JetBlue Airways2h 45m017:55Boston Logan AirportBoston Logan Airport19:40Chicago Midway AirportChicago Midway Airport0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 03/11/2026 17:55:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 03/11/2026 19:40:00. 50 Economy ticket for £75 per person are available. Travel duration is 2h 45m
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Frontier Airlines6h 32m012:15Boston Logan AirportBoston Logan Airport17:47Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 03/11/2026 12:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 03/11/2026 17:47:00. 50 Economy ticket for £99 per person are available. Travel duration is 6h 32m
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Frontier Airlines12h 32m012:15Boston Logan AirportBoston Logan Airport23:47Chicago Midway AirportChicago Midway Airport0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 03/11/2026 12:15:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 03/11/2026 23:47:00. 50 Economy ticket for £104 per person are available. Travel duration is 12h 32m
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JetBlue Airways3h 1m009:59Boston Logan AirportBoston Logan Airport12:00Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 03/11/2026 09:59:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 03/11/2026 12:00:00. 50 Economy ticket for £125 per person are available. Travel duration is 3h 1m
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United Airlines3h 0m006:00Boston Logan AirportBoston Logan Airport08:00Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 03/11/2026 06:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 03/11/2026 08:00:00. 50 Economy ticket for £127 per person are available. Travel duration is 3h 0m
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FlixBus35h 10m021:50Boston, MAAtlantic and Beach St08:00ChicagoCanal & Van Buren0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 03/11/2026 21:50:00 to Canal & Van Buren, Chicago (USA) arriving at 05/11/2026 08:00:00. 50 Economy ticket for £76 per person are available. Travel duration is 35h 10m
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Greyhound US22h 30m012:30Boston, MAAtlantic and Beach St10:00ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 03/11/2026 12:30:00 to Downtown Coach Station, Chicago (USA) arriving at 04/11/2026 10:00:00. 50 Economy ticket for £76 per person are available. Travel duration is 22h 30m
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Greyhound US28h 20m016:45Boston, MAAtlantic and Beach St20:05ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 03/11/2026 16:45:00 to Downtown Coach Station, Chicago (USA) arriving at 04/11/2026 20:05:00. 50 Economy ticket for £77 per person are available. Travel duration is 28h 20m
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FlixBus33h 20m021:50Boston, MAAtlantic and Beach St06:10ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 03/11/2026 21:50:00 to Downtown Coach Station, Chicago (USA) arriving at 05/11/2026 06:10:00. 50 Economy ticket for £79 per person are available. Travel duration is 33h 20m
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Greyhound US25h 50m012:30Boston, MASouth Station13:20Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from South Station, Boston, MA (USA) at 03/11/2026 12:30:00 to 95th Red Line Station, Chicago (USA) arriving at 04/11/2026 13:20:00. 50 Economy ticket for £81 per person are available. Travel duration is 25h 50m
Cheapest Flights Tuesday
Cheapest Buses Tuesday
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Greyhound US25h 55m012:30Boston, MAAtlantic and Beach St13:25Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 04/11/2026 12:30:00 to 95th Red Line Station, Chicago (USA) arriving at 05/11/2026 13:25:00. 50 Economy ticket for £77 per person are available. Travel duration is 25h 55m
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Greyhound US29h 10m001:30Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 04/11/2026 01:30:00 to 95th Red Line Station, Chicago (USA) arriving at 05/11/2026 05:40:00. 50 Economy ticket for £78 per person are available. Travel duration is 29h 10m
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Greyhound US28h 20m015:05Boston, MAAtlantic and Beach St18:25Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 04/11/2026 15:05:00 to 95th Red Line Station, Chicago (USA) arriving at 05/11/2026 18:25:00. 50 Economy ticket for £78 per person are available. Travel duration is 28h 20m
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FlixBus32h 50m002:30Boston, MAAtlantic and Beach St10:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 04/11/2026 02:30:00 to 95th Red Line Station, Chicago (USA) arriving at 05/11/2026 10:20:00. 50 Economy ticket for £80 per person are available. Travel duration is 32h 50m
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FlixBus37h 30m021:50Boston, MAAtlantic and Beach St10:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 04/11/2026 21:50:00 to 95th Red Line Station, Chicago (USA) arriving at 06/11/2026 10:20:00. 50 Economy ticket for £80 per person are available. Travel duration is 37h 30m
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Frontier Airlines6h 51m012:39Boston Logan AirportBoston Logan Airport18:30Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 04/11/2026 12:39:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 04/11/2026 18:30:00. 50 Economy ticket for £93 per person are available. Travel duration is 6h 51m
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United Airlines3h 0m006:00Boston Logan AirportBoston Logan Airport08:00Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 04/11/2026 06:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 04/11/2026 08:00:00. 50 Economy ticket for £119 per person are available. Travel duration is 3h 0m
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United Airlines3h 3m007:31Boston Logan AirportBoston Logan Airport09:34Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 04/11/2026 07:31:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 04/11/2026 09:34:00. 50 Economy ticket for £119 per person are available. Travel duration is 3h 3m
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JetBlue Airways3h 1m009:59Boston Logan AirportBoston Logan Airport12:00Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 04/11/2026 09:59:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 04/11/2026 12:00:00. 50 Economy ticket for £120 per person are available. Travel duration is 3h 1m
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Frontier Airlines21h 21m012:39Boston Logan AirportBoston Logan Airport09:00Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 04/11/2026 12:39:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 05/11/2026 09:00:00. 50 Economy ticket for £167 per person are available. Travel duration is 21h 21m
Cheapest Buses Wednesday
Cheapest Flights Wednesday
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Greyhound US25h 50m012:30Boston, MAAtlantic and Beach St13:20Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 05/11/2026 12:30:00 to 95th Red Line Station, Chicago (USA) arriving at 06/11/2026 13:20:00. 50 Economy ticket for £94 per person are available. Travel duration is 25h 50m
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Greyhound US22h 30m012:30Boston, MAAtlantic and Beach St10:00ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 05/11/2026 12:30:00 to Downtown Coach Station, Chicago (USA) arriving at 06/11/2026 10:00:00. 50 Economy ticket for £94 per person are available. Travel duration is 22h 30m
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FlixBus22h 40m015:45Boston, MAAtlantic and Beach St13:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 05/11/2026 15:45:00 to Downtown Coach Station, Chicago (USA) arriving at 06/11/2026 13:25:00. 50 Economy ticket for £95 per person are available. Travel duration is 22h 40m
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Greyhound US25h 50m012:30Boston, MASouth Station13:20Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from South Station, Boston, MA (USA) at 05/11/2026 12:30:00 to 95th Red Line Station, Chicago (USA) arriving at 06/11/2026 13:20:00. 50 Economy ticket for £97 per person are available. Travel duration is 25h 50m
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FlixBus27h 40m015:45Boston, MAAtlantic and Beach St18:25Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 05/11/2026 15:45:00 to 95th Red Line Station, Chicago (USA) arriving at 06/11/2026 18:25:00. 50 Economy ticket for £98 per person are available. Travel duration is 27h 40m
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United Airlines3h 0m006:00Boston Logan AirportBoston Logan Airport08:00Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 05/11/2026 06:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 05/11/2026 08:00:00. 50 Economy ticket for £120 per person are available. Travel duration is 3h 0m
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JetBlue Airways3h 12m017:05Boston Logan AirportBoston Logan Airport19:17Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 05/11/2026 17:05:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 05/11/2026 19:17:00. 50 Economy ticket for £121 per person are available. Travel duration is 3h 12m
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Frontier Airlines7h 6m012:39Boston Logan AirportBoston Logan Airport18:45Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 05/11/2026 12:39:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 05/11/2026 18:45:00. 50 Economy ticket for £155 per person are available. Travel duration is 7h 6m
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Sun Country Airlines7h 0m012:05Boston Logan AirportBoston Logan Airport18:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Sun Country Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 05/11/2026 12:05:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 05/11/2026 18:05:00. 50 Economy ticket for £167 per person are available. Travel duration is 7h 0m
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Allegiant Air12h 23m012:34Boston Logan AirportBoston Logan Airport23:57Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Allegiant Air goes from Boston Logan Airport, Boston Logan Airport (USA) at 05/11/2026 12:34:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 05/11/2026 23:57:00. 50 Economy ticket for £207 per person are available. Travel duration is 12h 23m
Cheapest Buses Thursday
Cheapest Flights Thursday
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Greyhound US25h 50m012:30Boston, MAAtlantic and Beach St13:20Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 06/11/2026 12:30:00 to 95th Red Line Station, Chicago (USA) arriving at 07/11/2026 13:20:00. 50 Economy ticket for £92 per person are available. Travel duration is 25h 50m
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FlixBus27h 40m015:45Boston, MAAtlantic and Beach St18:25Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 06/11/2026 15:45:00 to 95th Red Line Station, Chicago (USA) arriving at 07/11/2026 18:25:00. 50 Economy ticket for £92 per person are available. Travel duration is 27h 40m
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Greyhound US31h 45m016:45Boston, MAAtlantic and Beach St23:30Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 06/11/2026 16:45:00 to 95th Red Line Station, Chicago (USA) arriving at 07/11/2026 23:30:00. 50 Economy ticket for £94 per person are available. Travel duration is 31h 45m
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Greyhound US22h 30m012:30Boston, MAAtlantic and Beach St10:00ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 06/11/2026 12:30:00 to Downtown Coach Station, Chicago (USA) arriving at 07/11/2026 10:00:00. 50 Economy ticket for £94 per person are available. Travel duration is 22h 30m
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FlixBus22h 40m015:45Boston, MAAtlantic and Beach St13:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 06/11/2026 15:45:00 to Downtown Coach Station, Chicago (USA) arriving at 07/11/2026 13:25:00. 50 Economy ticket for £94 per person are available. Travel duration is 22h 40m
Cheapest Buses Friday
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Greyhound US29h 10m001:30Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 07/11/2026 01:30:00 to 95th Red Line Station, Chicago (USA) arriving at 08/11/2026 05:40:00. 50 Economy ticket for £104 per person are available. Travel duration is 29h 10m
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FlixBus27h 40m015:45Boston, MAAtlantic and Beach St18:25Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 07/11/2026 15:45:00 to 95th Red Line Station, Chicago (USA) arriving at 08/11/2026 18:25:00. 50 Economy ticket for £104 per person are available. Travel duration is 27h 40m
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Greyhound US25h 50m012:30Boston, MAAtlantic and Beach St13:20Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 07/11/2026 12:30:00 to 95th Red Line Station, Chicago (USA) arriving at 08/11/2026 13:20:00. 50 Economy ticket for £105 per person are available. Travel duration is 25h 50m
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Greyhound US22h 30m012:30Boston, MAAtlantic and Beach St10:00ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 07/11/2026 12:30:00 to Downtown Coach Station, Chicago (USA) arriving at 08/11/2026 10:00:00. 50 Economy ticket for £108 per person are available. Travel duration is 22h 30m
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FlixBus22h 40m015:45Boston, MAAtlantic and Beach St13:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 07/11/2026 15:45:00 to Downtown Coach Station, Chicago (USA) arriving at 08/11/2026 13:25:00. 50 Economy ticket for £108 per person are available. Travel duration is 22h 40m
Cheapest Buses Saturday
What are the fastest trips from Boston, MA to Chicago?
You can get to Chicago from Boston, MA in just 2h 45m with a Flight from JetBlue Airways. But this is just one option, click on any of the offers below to compare it with the other available modes of transportations.
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Greyhound US31h 45m016:45Boston, MASouth Station23:30Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from South Station, Boston, MA (USA) at 01/11/2026 16:45:00 to 95th Red Line Station, Chicago (USA) arriving at 02/11/2026 23:30:00. 50 Economy ticket for £175 per person are available. Travel duration is 31h 45m
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Greyhound US31h 45m016:45Boston, MAAtlantic and Beach St23:30Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 01/11/2026 16:45:00 to 95th Red Line Station, Chicago (USA) arriving at 02/11/2026 23:30:00. 50 Economy ticket for £177 per person are available. Travel duration is 31h 45m
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FlixBus33h 20m021:50Boston, MAAtlantic and Beach St06:10ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 01/11/2026 21:50:00 to Downtown Coach Station, Chicago (USA) arriving at 03/11/2026 06:10:00. 50 Economy ticket for £154 per person are available. Travel duration is 33h 20m
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FlixBus37h 30m021:50Boston, MAAtlantic and Beach St10:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 01/11/2026 21:50:00 to 95th Red Line Station, Chicago (USA) arriving at 03/11/2026 10:20:00. 50 Economy ticket for £144 per person are available. Travel duration is 37h 30m
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FlixBus37h 30m021:50Boston, MASouth Station10:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from South Station, Boston, MA (USA) at 01/11/2026 21:50:00 to 95th Red Line Station, Chicago (USA) arriving at 03/11/2026 10:20:00. 50 Economy ticket for £146 per person are available. Travel duration is 37h 30m
Fastest Buses Sunday
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JetBlue Airways2h 45m018:30Boston Logan AirportBoston Logan Airport20:15Chicago Midway AirportChicago Midway Airport0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 02/11/2026 18:30:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 02/11/2026 20:15:00. 50 Economy ticket for £125 per person are available. Travel duration is 2h 45m
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United Airlines3h 0m006:00Boston Logan AirportBoston Logan Airport08:00Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 02/11/2026 06:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 02/11/2026 08:00:00. 50 Economy ticket for £127 per person are available. Travel duration is 3h 0m
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JetBlue Airways3h 1m009:59Boston Logan AirportBoston Logan Airport12:00Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 02/11/2026 09:59:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 02/11/2026 12:00:00. 50 Economy ticket for £126 per person are available. Travel duration is 3h 1m
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United Airlines3h 3m007:31Boston Logan AirportBoston Logan Airport09:34Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 02/11/2026 07:31:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 02/11/2026 09:34:00. 50 Economy ticket for £127 per person are available. Travel duration is 3h 3m
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JetBlue Airways3h 12m017:05Boston Logan AirportBoston Logan Airport19:17Chicago Midway AirportChicago Midway Airport0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 02/11/2026 17:05:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 02/11/2026 19:17:00. 50 Economy ticket for £74 per person are available. Travel duration is 3h 12m
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JetBlue Airways3h 12m017:05Boston Logan AirportBoston Logan Airport19:17Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 02/11/2026 17:05:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 02/11/2026 19:17:00. 50 Economy ticket for £126 per person are available. Travel duration is 3h 12m
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Greyhound US22h 30m012:30Boston, MAAtlantic and Beach St10:00ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 02/11/2026 12:30:00 to Downtown Coach Station, Chicago (USA) arriving at 03/11/2026 10:00:00. 50 Economy ticket for £100 per person are available. Travel duration is 22h 30m
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Greyhound US25h 10m006:00Boston, MAAtlantic and Beach St06:10ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 02/11/2026 06:00:00 to Downtown Coach Station, Chicago (USA) arriving at 03/11/2026 06:10:00. 50 Economy ticket for £103 per person are available. Travel duration is 25h 10m
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FlixBus27h 50m017:15Boston, MAAtlantic and Beach St20:05ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 02/11/2026 17:15:00 to Downtown Coach Station, Chicago (USA) arriving at 03/11/2026 20:05:00. 50 Economy ticket for £108 per person are available. Travel duration is 27h 50m
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FlixBus27h 50m017:15Boston, MASouth Station20:05ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from South Station, Boston, MA (USA) at 02/11/2026 17:15:00 to Downtown Coach Station, Chicago (USA) arriving at 03/11/2026 20:05:00. 50 Economy ticket for £111 per person are available. Travel duration is 27h 50m
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Greyhound US28h 20m016:45Boston, MAAtlantic and Beach St20:05ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 02/11/2026 16:45:00 to Downtown Coach Station, Chicago (USA) arriving at 03/11/2026 20:05:00. 50 Economy ticket for £100 per person are available. Travel duration is 28h 20m
Fastest Flights Monday
Fastest Buses Monday
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JetBlue Airways2h 45m017:55Boston Logan AirportBoston Logan Airport19:40Chicago Midway AirportChicago Midway Airport0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 03/11/2026 17:55:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 03/11/2026 19:40:00. 50 Economy ticket for £75 per person are available. Travel duration is 2h 45m
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United Airlines3h 0m006:00Boston Logan AirportBoston Logan Airport08:00Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 03/11/2026 06:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 03/11/2026 08:00:00. 50 Economy ticket for £127 per person are available. Travel duration is 3h 0m
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JetBlue Airways3h 1m009:59Boston Logan AirportBoston Logan Airport12:00Chicago Midway AirportChicago Midway Airport0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 03/11/2026 09:59:00 to Chicago Midway Airport, Chicago Midway Airport (USA) arriving at 03/11/2026 12:00:00. 50 Economy ticket for £74 per person are available. Travel duration is 3h 1m
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JetBlue Airways3h 1m009:59Boston Logan AirportBoston Logan Airport12:00Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 03/11/2026 09:59:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 03/11/2026 12:00:00. 50 Economy ticket for £125 per person are available. Travel duration is 3h 1m
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United Airlines3h 3m007:31Boston Logan AirportBoston Logan Airport09:34Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 03/11/2026 07:31:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 03/11/2026 09:34:00. 50 Economy ticket for £127 per person are available. Travel duration is 3h 3m
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United Airlines3h 3m009:12Boston Logan AirportBoston Logan Airport11:15Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 03/11/2026 09:12:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 03/11/2026 11:15:00. 50 Economy ticket for £127 per person are available. Travel duration is 3h 3m
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Greyhound US22h 30m012:30Boston, MAAtlantic and Beach St10:00ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 03/11/2026 12:30:00 to Downtown Coach Station, Chicago (USA) arriving at 04/11/2026 10:00:00. 50 Economy ticket for £76 per person are available. Travel duration is 22h 30m
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Greyhound US25h 50m012:30Boston, MASouth Station13:20Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from South Station, Boston, MA (USA) at 03/11/2026 12:30:00 to 95th Red Line Station, Chicago (USA) arriving at 04/11/2026 13:20:00. 50 Economy ticket for £81 per person are available. Travel duration is 25h 50m
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Greyhound US28h 20m016:45Boston, MAAtlantic and Beach St20:05ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 03/11/2026 16:45:00 to Downtown Coach Station, Chicago (USA) arriving at 04/11/2026 20:05:00. 50 Economy ticket for £77 per person are available. Travel duration is 28h 20m
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FlixBus33h 20m021:50Boston, MAAtlantic and Beach St06:10ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 03/11/2026 21:50:00 to Downtown Coach Station, Chicago (USA) arriving at 05/11/2026 06:10:00. 50 Economy ticket for £79 per person are available. Travel duration is 33h 20m
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FlixBus35h 10m021:50Boston, MAAtlantic and Beach St08:00ChicagoCanal & Van Buren0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 03/11/2026 21:50:00 to Canal & Van Buren, Chicago (USA) arriving at 05/11/2026 08:00:00. 50 Economy ticket for £76 per person are available. Travel duration is 35h 10m
Fastest Flights Tuesday
Fastest Buses Tuesday
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United Airlines3h 0m006:00Boston Logan AirportBoston Logan Airport08:00Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 04/11/2026 06:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 04/11/2026 08:00:00. 50 Economy ticket for £119 per person are available. Travel duration is 3h 0m
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JetBlue Airways3h 1m009:59Boston Logan AirportBoston Logan Airport12:00Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 04/11/2026 09:59:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 04/11/2026 12:00:00. 50 Economy ticket for £120 per person are available. Travel duration is 3h 1m
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United Airlines3h 3m007:31Boston Logan AirportBoston Logan Airport09:34Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 04/11/2026 07:31:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 04/11/2026 09:34:00. 50 Economy ticket for £119 per person are available. Travel duration is 3h 3m
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Frontier Airlines6h 51m012:39Boston Logan AirportBoston Logan Airport18:30Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 04/11/2026 12:39:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 04/11/2026 18:30:00. 50 Economy ticket for £93 per person are available. Travel duration is 6h 51m
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Frontier Airlines21h 21m012:39Boston Logan AirportBoston Logan Airport09:00Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 04/11/2026 12:39:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 05/11/2026 09:00:00. 50 Economy ticket for £167 per person are available. Travel duration is 21h 21m
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Greyhound US25h 55m012:30Boston, MAAtlantic and Beach St13:25Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 04/11/2026 12:30:00 to 95th Red Line Station, Chicago (USA) arriving at 05/11/2026 13:25:00. 50 Economy ticket for £77 per person are available. Travel duration is 25h 55m
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Greyhound US28h 20m015:05Boston, MAAtlantic and Beach St18:25Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 04/11/2026 15:05:00 to 95th Red Line Station, Chicago (USA) arriving at 05/11/2026 18:25:00. 50 Economy ticket for £78 per person are available. Travel duration is 28h 20m
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Greyhound US29h 10m001:30Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 04/11/2026 01:30:00 to 95th Red Line Station, Chicago (USA) arriving at 05/11/2026 05:40:00. 50 Economy ticket for £78 per person are available. Travel duration is 29h 10m
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FlixBus32h 50m002:30Boston, MAAtlantic and Beach St10:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 04/11/2026 02:30:00 to 95th Red Line Station, Chicago (USA) arriving at 05/11/2026 10:20:00. 50 Economy ticket for £80 per person are available. Travel duration is 32h 50m
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FlixBus37h 30m021:50Boston, MAAtlantic and Beach St10:20Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 04/11/2026 21:50:00 to 95th Red Line Station, Chicago (USA) arriving at 06/11/2026 10:20:00. 50 Economy ticket for £80 per person are available. Travel duration is 37h 30m
Fastest Flights Wednesday
Fastest Buses Wednesday
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United Airlines3h 0m006:00Boston Logan AirportBoston Logan Airport08:00Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from United Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 05/11/2026 06:00:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 05/11/2026 08:00:00. 50 Economy ticket for £120 per person are available. Travel duration is 3h 0m
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JetBlue Airways3h 12m017:05Boston Logan AirportBoston Logan Airport19:17Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from JetBlue Airways goes from Boston Logan Airport, Boston Logan Airport (USA) at 05/11/2026 17:05:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 05/11/2026 19:17:00. 50 Economy ticket for £121 per person are available. Travel duration is 3h 12m
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Sun Country Airlines7h 0m012:05Boston Logan AirportBoston Logan Airport18:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Sun Country Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 05/11/2026 12:05:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 05/11/2026 18:05:00. 50 Economy ticket for £167 per person are available. Travel duration is 7h 0m
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Frontier Airlines7h 6m012:39Boston Logan AirportBoston Logan Airport18:45Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Frontier Airlines goes from Boston Logan Airport, Boston Logan Airport (USA) at 05/11/2026 12:39:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 05/11/2026 18:45:00. 50 Economy ticket for £155 per person are available. Travel duration is 7h 6m
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Allegiant Air12h 23m012:34Boston Logan AirportBoston Logan Airport23:57Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center0EconomyA Flight from Allegiant Air goes from Boston Logan Airport, Boston Logan Airport (USA) at 05/11/2026 12:34:00 to Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) arriving at 05/11/2026 23:57:00. 50 Economy ticket for £207 per person are available. Travel duration is 12h 23m
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Greyhound US22h 30m012:30Boston, MAAtlantic and Beach St10:00ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 05/11/2026 12:30:00 to Downtown Coach Station, Chicago (USA) arriving at 06/11/2026 10:00:00. 50 Economy ticket for £94 per person are available. Travel duration is 22h 30m
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FlixBus22h 40m015:45Boston, MAAtlantic and Beach St13:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 05/11/2026 15:45:00 to Downtown Coach Station, Chicago (USA) arriving at 06/11/2026 13:25:00. 50 Economy ticket for £95 per person are available. Travel duration is 22h 40m
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Greyhound US25h 50m012:30Boston, MAAtlantic and Beach St13:20Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 05/11/2026 12:30:00 to 95th Red Line Station, Chicago (USA) arriving at 06/11/2026 13:20:00. 50 Economy ticket for £94 per person are available. Travel duration is 25h 50m
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Greyhound US25h 50m012:30Boston, MASouth Station13:20Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from South Station, Boston, MA (USA) at 05/11/2026 12:30:00 to 95th Red Line Station, Chicago (USA) arriving at 06/11/2026 13:20:00. 50 Economy ticket for £97 per person are available. Travel duration is 25h 50m
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FlixBus27h 40m015:45Boston, MAAtlantic and Beach St18:25Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 05/11/2026 15:45:00 to 95th Red Line Station, Chicago (USA) arriving at 06/11/2026 18:25:00. 50 Economy ticket for £98 per person are available. Travel duration is 27h 40m
Fastest Flights Thursday
Fastest Buses Thursday
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Greyhound US22h 30m012:30Boston, MAAtlantic and Beach St10:00ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 06/11/2026 12:30:00 to Downtown Coach Station, Chicago (USA) arriving at 07/11/2026 10:00:00. 50 Economy ticket for £94 per person are available. Travel duration is 22h 30m
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FlixBus22h 40m015:45Boston, MAAtlantic and Beach St13:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 06/11/2026 15:45:00 to Downtown Coach Station, Chicago (USA) arriving at 07/11/2026 13:25:00. 50 Economy ticket for £94 per person are available. Travel duration is 22h 40m
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Greyhound US25h 50m012:30Boston, MAAtlantic and Beach St13:20Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 06/11/2026 12:30:00 to 95th Red Line Station, Chicago (USA) arriving at 07/11/2026 13:20:00. 50 Economy ticket for £92 per person are available. Travel duration is 25h 50m
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FlixBus27h 40m015:45Boston, MAAtlantic and Beach St18:25Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 06/11/2026 15:45:00 to 95th Red Line Station, Chicago (USA) arriving at 07/11/2026 18:25:00. 50 Economy ticket for £92 per person are available. Travel duration is 27h 40m
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Greyhound US31h 45m016:45Boston, MAAtlantic and Beach St23:30Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 06/11/2026 16:45:00 to 95th Red Line Station, Chicago (USA) arriving at 07/11/2026 23:30:00. 50 Economy ticket for £94 per person are available. Travel duration is 31h 45m
Fastest Buses Friday
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Greyhound US22h 30m012:30Boston, MAAtlantic and Beach St10:00ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 07/11/2026 12:30:00 to Downtown Coach Station, Chicago (USA) arriving at 08/11/2026 10:00:00. 50 Economy ticket for £108 per person are available. Travel duration is 22h 30m
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FlixBus22h 40m015:45Boston, MAAtlantic and Beach St13:25ChicagoDowntown Coach Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 07/11/2026 15:45:00 to Downtown Coach Station, Chicago (USA) arriving at 08/11/2026 13:25:00. 50 Economy ticket for £108 per person are available. Travel duration is 22h 40m
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Greyhound US25h 50m012:30Boston, MAAtlantic and Beach St13:20Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 07/11/2026 12:30:00 to 95th Red Line Station, Chicago (USA) arriving at 08/11/2026 13:20:00. 50 Economy ticket for £105 per person are available. Travel duration is 25h 50m
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FlixBus27h 40m015:45Boston, MAAtlantic and Beach St18:25Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 07/11/2026 15:45:00 to 95th Red Line Station, Chicago (USA) arriving at 08/11/2026 18:25:00. 50 Economy ticket for £104 per person are available. Travel duration is 27h 40m
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Greyhound US29h 10m001:30Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 07/11/2026 01:30:00 to 95th Red Line Station, Chicago (USA) arriving at 08/11/2026 05:40:00. 50 Economy ticket for £104 per person are available. Travel duration is 29h 10m
Fastest Buses Saturday
Here you will find all operators and timetables for a
Bus from Boston, MA to Chicago
What are the most popular stations in Boston, MA and Chicago?
In Boston, MA, you will usually depart from Atlantic and Beach St, South Station or Prudential Center T Transit Station, while in Chicago you will be arriving at California & 35th Street Coach Stop, Downtown Coach Station or 95th Red Line Station, but there are many more stops to explore in both locations.
How do I decide? Some tips and tricks from our experience
Are you having trouble deciding on how to get to Chicago from Boston, MA? With 9 connections between 2 Flight and Bus operators, it can be difficult to find the one ride that will make you happy. But we have some tips that can help you make the best informed decision. First of all, the best trip is always the one that meets all your needs, so make a list of all the things that you want from this journey and look for something that will satisfy all of them. Here we will go through some of the factors mostly commonly taken into consideration.
Look for the lowest price
Ticket price is usually the main concern: even if you can afford to pay more, why do it if there are cheaper options? Saving on the trip means that you can spend more on the vacation itself! Between Boston, MA and Chicago, you can pay as low as £74 with a Flight from JetBlue Airways.Travel duration
Time is also an important factor. An earlier departure may allow you to see a beautiful sunset or relax before an important event. And remember, time is money, so paying more for a shorter trip may be well worth it. For longer distances, flights are without doubt the best options, but be mindful of airport times and possible delays: a high-speed train may end up cheaper and faster! Here the quicker option is definitely the Flight from JetBlue Airways: you will get to Chicago in just 2h 45m.Comfort makes all the difference
You should always take into account what your personal travelling preferences are. Is one hand luggage enough, or are you trasporting more? Would you like to have a snack during the journey? Can you relax in a busy compartment, or do you need space for yourself? Even among the same mode of transportation, different companies will offer you varying levels of comfort and amenities. The main operators connecting Boston, MA and Chicago are Greyhound US, FlixBus and JetBlue Airways, but be sure to check what they have to offer!Save money with deals, and always compare
One last tip? Even if you live in Boston, MA and Chicago is your only destination, it may be wise to check the offers from and to nearby cities or, if you are flyng, nearby airports. Check the trips from Boston Logan Airport or to Cicero, IL, and look at flights from Boston Logan Airport, and landing at Chicago Midway Airport. Comparing different routes may allow you to find deals or promotions you were not aware of. Consider also signing up to CheckMyBus to see even more exclusive promotions!Which companies offer a trip from Boston, MA to Chicago?
The most popular companies between Boston, MA and Chicago, are Greyhound US, FlixBus and JetBlue Airways. Be sure to check their seat class offers and the amenities that they provide.
Bus companies: Greyhound US and FlixBus
Airlines: JetBlue Airways, United Airlines, Frontier Airlines and 2 more.
All you need to know when you travel from Boston, MA to Chicago
Check all information on comfort and services on all modes of transports from Boston, MA to Chicago. See which seat classes are available, and what amenities are other advantages offered by the operators on your journey.
FAQs about the trip from Boston, MA to Chicago
How can I reach Chicago from Boston, MA?
Every day, there are on average 9 connections between Flight and Bus, with which you can get to Chicago from Boston, MA.
How far is Chicago from Boston, MA?
The distance between Boston, MA and Chicago is 1,366.8 km.
What is the most ecofriendly mode of transport between Boston, MA and Chicago?
Trains and buses are by far the greenest options, with trains surpassing buses on longer routes. Planes will always be the worst polluters, especially in shorter flights, were the emissions from the takeoff and landing are less offset by the distance.
On this particular route, a bus will emit, per person, a total of 37 kgs of CO2, a train 48 kgs, a car 232 kgs, and a flight 336 kgs.
What is the cheapest mode of transport from Boston, MA to Chicago?
You can get to Chicago with just £74 by taking a Flight from JetBlue Airways.
What is the fastest way to get from Boston, MA to Chicago?
While a plane is travelling fastest boarding and transfer to airport consumes a lot of time. Usually, high speed trains are better than flights if pure train travel time is below 4 hours. For this particular route, you can get to Chicago in just 2h 45m with a Flight from JetBlue Airways.
More routes to Boston, MA and to Chicago
Looking for more options? Here you can see the most popular routes to Boston, MA and to Chicago. Simply click on a connection, and you’ll find all the details about the route!
- Trips to Boston, MA
- Arlington, VA to Boston, MA
- Atlanta, GA to Boston, MA
- Fort Lauderdale, FL to Boston, MA
- Greensboro, NC to Boston, MA
- Jacksonville, FL to Boston, MA
- Miami Airport to Boston, MA
- Montreal to Boston, MA
- New York to Boston, MA
- Newark to Boston, MA
- Orlando, FL to Boston, MA
- Ottawa, ON to Boston, MA
- Pittsburgh to Boston, MA
- Toronto, ON to Boston, MA
- Washington, DC to Boston, MA
- Trips to Chicago
- Aguascalientes to Chicago
- Atlanta, GA to Chicago
- Cincinnati to Chicago
- Ciudad Juárez to Chicago
- Cleveland to Chicago
- Columbus, OH to Chicago
- Dallas to Chicago
- El Paso, TX to Chicago
- Guadalajara, JC to Chicago
- Houston to Chicago
- Las Vegas to Chicago
- Memphis to Chicago
- Morelia to Chicago
- Nashville to Chicago
- New York to Chicago
- Newark to Chicago
- Orlando, FL to Chicago
- Phoenix, AZ to Chicago
- Pittsburgh to Chicago
- San Antonio, TX to Chicago
- Toronto, ON to Chicago
- West Palm Beach, FL to Chicago
