What is the best way to travel from Chicago to Boston, MA?
Looking for a trip? Check and compare all the available Buses and Flights to Boston, MA from Chicago. 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 Boston, MA from Chicago?
You can reach Boston, MA with just £59 by taking a Bus from Greyhound US, 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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United Airlines2h 35m015:55Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center19:30Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 03/06/2026 15:55:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 03/06/2026 19:30:00. 50 Economy ticket for £61 per person are available. Travel duration is 2h 35m
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United Airlines2h 36m019:45Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center23:21Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 03/06/2026 19:45:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 03/06/2026 23:21:00. 50 Economy ticket for £61 per person are available. Travel duration is 2h 36m
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Frontier Airlines12h 20m012:04Chicago Midway AirportChicago Midway Airport01:24Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 03/06/2026 12:04:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 04/06/2026 01:24:00. 50 Economy ticket for £70 per person are available. Travel duration is 12h 20m
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Frontier Airlines18h 45m012:04Chicago Midway AirportChicago Midway Airport07:49Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 03/06/2026 12:04:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 04/06/2026 07:49:00. 50 Economy ticket for £80 per person are available. Travel duration is 18h 45m
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JetBlue Airways7h 32m015:27Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center23:59Boston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 03/06/2026 15:27:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 03/06/2026 23:59:00. 50 Economy ticket for £122 per person are available. Travel duration is 7h 32m
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FlixBus25h 35m019:15ChicagoDowntown Coach Station21:50Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 03/06/2026 19:15:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 04/06/2026 21:50:00. 50 Economy ticket for £114 per person are available. Travel duration is 25h 35m
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Greyhound US33h 10m022:50ChicagoDowntown Coach Station09:00Boston, MAAllston0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 03/06/2026 22:50:00 to Allston, Boston, MA (USA) arriving at 05/06/2026 09:00:00. 50 Economy ticket for £118 per person are available. Travel duration is 33h 10m
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Greyhound US33h 15m023:10ChicagoUnion Station09:25Boston, MASouth Station0EconomyA Bus from Greyhound US goes from Union Station, Chicago (USA) at 03/06/2026 23:10:00 to South Station, Boston, MA (USA) arriving at 05/06/2026 09:25:00. 50 Economy ticket for £118 per person are available. Travel duration is 33h 15m
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Greyhound US32h 50m023:10ChicagoUnion Station09:00Boston, MAAllston0EconomyA Bus from Greyhound US goes from Union Station, Chicago (USA) at 03/06/2026 23:10:00 to Allston, Boston, MA (USA) arriving at 05/06/2026 09:00:00. 50 Economy ticket for £118 per person are available. Travel duration is 32h 50m
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FlixBus25h 10m019:40Chicago95th Red Line Station21:50Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 03/06/2026 19:40:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 04/06/2026 21:50:00. 50 Economy ticket for £126 per person are available. Travel duration is 25h 10m
Cheapest Flights Wednesday
Cheapest Buses Wednesday
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Greyhound US23h 25m018:00ChicagoDowntown Coach Station18:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 04/06/2026 18:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 05/06/2026 18:25:00. 50 Economy ticket for £66 per person are available. Travel duration is 23h 25m
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FlixBus25h 35m019:15ChicagoDowntown Coach Station21:50Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 04/06/2026 19:15:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 05/06/2026 21:50:00. 50 Economy ticket for £66 per person are available. Travel duration is 25h 35m
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FlixBus22h 35m012:25ChicagoDowntown Coach Station12:00Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 04/06/2026 12:25:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 05/06/2026 12:00:00. 50 Economy ticket for £67 per person are available. Travel duration is 22h 35m
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Greyhound US27h 25m007:00ChicagoDowntown Coach Station11:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 04/06/2026 07:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 05/06/2026 11:25:00. 50 Economy ticket for £69 per person are available. Travel duration is 27h 25m
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FlixBus23h 55m011:05Chicago95th Red Line Station12:00Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 04/06/2026 11:05:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 05/06/2026 12:00:00. 50 Economy ticket for £70 per person are available. Travel duration is 23h 55m
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United Airlines2h 24m006:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center09:29Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 04/06/2026 06:05:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 04/06/2026 09:29:00. 50 Economy ticket for £66 per person are available. Travel duration is 2h 24m
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JetBlue Airways2h 29m020:30Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center23:59Boston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 04/06/2026 20:30:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 04/06/2026 23:59:00. 50 Economy ticket for £72 per person are available. Travel duration is 2h 29m
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Frontier Airlines17h 29m006:55Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center01:24Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 04/06/2026 06:55:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 05/06/2026 01:24:00. 50 Economy ticket for £82 per person are available. Travel duration is 17h 29m
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Sun Country Airlines14h 8m018:25Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center09:33Boston Logan AirportBoston Logan Airport0EconomyA Flight from Sun Country Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 04/06/2026 18:25:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 05/06/2026 09:33:00. 50 Economy ticket for £178 per person are available. Travel duration is 14h 8m
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Alaska Airlines14h 34m014:10Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center05:44Boston Logan AirportBoston Logan Airport0EconomyA Flight from Alaska Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 04/06/2026 14:10:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 05/06/2026 05:44:00. 50 Economy ticket for £269 per person are available. Travel duration is 14h 34m
Cheapest Buses Thursday
Cheapest Flights Thursday
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JetBlue Airways2h 29m020:30Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center23:59Boston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 05/06/2026 20:30:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 05/06/2026 23:59:00. 50 Economy ticket for £64 per person are available. Travel duration is 2h 29m
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United Airlines2h 36m018:20Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center21:56Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 05/06/2026 18:20:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 05/06/2026 21:56:00. 50 Economy ticket for £65 per person are available. Travel duration is 2h 36m
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Frontier Airlines12h 20m012:04Chicago Midway AirportChicago Midway Airport01:24Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 05/06/2026 12:04:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 06/06/2026 01:24:00. 50 Economy ticket for £89 per person are available. Travel duration is 12h 20m
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Allegiant Air11h 41m021:23Chicago Midway AirportChicago Midway Airport10:04Boston Logan AirportBoston Logan Airport0EconomyA Flight from Allegiant Air goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 05/06/2026 21:23:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 06/06/2026 10:04:00. 50 Economy ticket for £99 per person are available. Travel duration is 11h 41m
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Sun Country Airlines15h 13m018:25Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center10:38Boston Logan AirportBoston Logan Airport0EconomyA Flight from Sun Country Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 05/06/2026 18:25:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 06/06/2026 10:38:00. 50 Economy ticket for £184 per person are available. Travel duration is 15h 13m
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FlixBus22h 35m012:25ChicagoDowntown Coach Station12:00Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 05/06/2026 12:25:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 06/06/2026 12:00:00. 50 Economy ticket for £122 per person are available. Travel duration is 22h 35m
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Greyhound US27h 25m007:00ChicagoDowntown Coach Station11:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 05/06/2026 07:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 06/06/2026 11:25:00. 50 Economy ticket for £123 per person are available. Travel duration is 27h 25m
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Greyhound US23h 25m018:00ChicagoDowntown Coach Station18:25Boston, MASouth Station0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 05/06/2026 18:00:00 to South Station, Boston, MA (USA) arriving at 06/06/2026 18:25:00. 50 Economy ticket for £124 per person are available. Travel duration is 23h 25m
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Greyhound US23h 25m018:00ChicagoDowntown Coach Station18:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 05/06/2026 18:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 06/06/2026 18:25:00. 50 Economy ticket for £124 per person are available. Travel duration is 23h 25m
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FlixBus22h 35m012:25ChicagoDowntown Coach Station12:00Boston, MASouth Station0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 05/06/2026 12:25:00 to South Station, Boston, MA (USA) arriving at 06/06/2026 12:00:00. 50 Economy ticket for £125 per person are available. Travel duration is 22h 35m
Cheapest Flights Friday
Cheapest Buses Friday
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United Airlines2h 34m013:55Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center17:29Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 06/06/2026 13:55:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 06/06/2026 17:29:00. 50 Economy ticket for £72 per person are available. Travel duration is 2h 34m
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United Airlines2h 35m015:55Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center19:30Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 06/06/2026 15:55:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 06/06/2026 19:30:00. 50 Economy ticket for £72 per person are available. Travel duration is 2h 35m
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Frontier Airlines12h 25m011:59Chicago Midway AirportChicago Midway Airport01:24Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 06/06/2026 11:59:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 07/06/2026 01:24:00. 50 Economy ticket for £84 per person are available. Travel duration is 12h 25m
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Frontier Airlines10h 55m013:29Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center01:24Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 06/06/2026 13:29:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 07/06/2026 01:24:00. 50 Economy ticket for £84 per person are available. Travel duration is 10h 55m
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JetBlue Airways2h 29m013:55Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center17:24Boston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 06/06/2026 13:55:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 06/06/2026 17:24:00. 50 Economy ticket for £97 per person are available. Travel duration is 2h 29m
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Greyhound US27h 25m007:00ChicagoDowntown Coach Station11:25Boston, MASouth Station0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 06/06/2026 07:00:00 to South Station, Boston, MA (USA) arriving at 07/06/2026 11:25:00. 50 Economy ticket for £95 per person are available. Travel duration is 27h 25m
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Greyhound US27h 25m007:00ChicagoDowntown Coach Station11:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 06/06/2026 07:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 07/06/2026 11:25:00. 50 Economy ticket for £95 per person are available. Travel duration is 27h 25m
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FlixBus33h 25m019:15ChicagoDowntown Coach Station05:40Boston, MAAllston0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 06/06/2026 19:15:00 to Allston, Boston, MA (USA) arriving at 08/06/2026 05:40:00. 50 Economy ticket for £106 per person are available. Travel duration is 33h 25m
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Greyhound US23h 25m018:00ChicagoDowntown Coach Station18:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 06/06/2026 18:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 07/06/2026 18:25:00. 50 Economy ticket for £112 per person are available. Travel duration is 23h 25m
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FlixBus25h 35m019:15ChicagoDowntown Coach Station21:50Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 06/06/2026 19:15:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 07/06/2026 21:50:00. 50 Economy ticket for £113 per person are available. Travel duration is 25h 35m
Cheapest Flights Saturday
Cheapest Buses Saturday
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United Airlines2h 24m006:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center09:29Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 07/06/2026 06:05:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 07/06/2026 09:29:00. 50 Economy ticket for £88 per person are available. Travel duration is 2h 24m
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Frontier Airlines24h 49m006:00Chicago Midway AirportChicago Midway Airport07:49Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 07/06/2026 06:00:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 08/06/2026 07:49:00. 50 Economy ticket for £170 per person are available. Travel duration is 24h 49m
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Sun Country Airlines15h 17m018:39Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center10:56Boston Logan AirportBoston Logan Airport0EconomyA Flight from Sun Country Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 07/06/2026 18:39:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 08/06/2026 10:56:00. 50 Economy ticket for £213 per person are available. Travel duration is 15h 17m
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JetBlue Airways2h 30m008:49Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center12:19Boston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 07/06/2026 08:49:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 07/06/2026 12:19:00. 50 Economy ticket for £234 per person are available. Travel duration is 2h 30m
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Alaska Airlines19h 44m009:00Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center05:44Boston Logan AirportBoston Logan Airport0EconomyA Flight from Alaska Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 07/06/2026 09:00:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 08/06/2026 05:44:00. 50 Economy ticket for £255 per person are available. Travel duration is 19h 44m
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FlixBus22h 35m012:25ChicagoDowntown Coach Station12:00Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 07/06/2026 12:25:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 08/06/2026 12:00:00. 50 Economy ticket for £105 per person are available. Travel duration is 22h 35m
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Greyhound US33h 15m023:10ChicagoCanal & Van Buren09:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Canal & Van Buren, Chicago (USA) at 07/06/2026 23:10:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 09/06/2026 09:25:00. 50 Economy ticket for £108 per person are available. Travel duration is 33h 15m
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Greyhound US33h 15m023:10ChicagoUnion Station09:25Boston, MASouth Station0EconomyA Bus from Greyhound US goes from Union Station, Chicago (USA) at 07/06/2026 23:10:00 to South Station, Boston, MA (USA) arriving at 09/06/2026 09:25:00. 50 Economy ticket for £111 per person are available. Travel duration is 33h 15m
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Greyhound US32h 50m023:10ChicagoUnion Station09:00Boston, MAAllston0EconomyA Bus from Greyhound US goes from Union Station, Chicago (USA) at 07/06/2026 23:10:00 to Allston, Boston, MA (USA) arriving at 09/06/2026 09:00:00. 50 Economy ticket for £111 per person are available. Travel duration is 32h 50m
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FlixBus23h 55m011:05Chicago95th Red Line Station12:00Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 07/06/2026 11:05:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 08/06/2026 12:00:00. 50 Economy ticket for £118 per person are available. Travel duration is 23h 55m
Cheapest Flights Sunday
Cheapest Buses Sunday
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United Airlines2h 33m021:41Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center01:14Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 08/06/2026 21:41:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 09/06/2026 01:14:00. 50 Economy ticket for £72 per person are available. Travel duration is 2h 33m
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JetBlue Airways2h 29m020:30Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center23:59Boston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 08/06/2026 20:30:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 08/06/2026 23:59:00. 50 Economy ticket for £82 per person are available. Travel duration is 2h 29m
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Frontier Airlines18h 48m012:04Chicago Midway AirportChicago Midway Airport07:52Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 08/06/2026 12:04:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 09/06/2026 07:52:00. 50 Economy ticket for £118 per person are available. Travel duration is 18h 48m
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Sun Country Airlines14h 29m019:09Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center10:38Boston Logan AirportBoston Logan Airport0EconomyA Flight from Sun Country Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 08/06/2026 19:09:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 09/06/2026 10:38:00. 50 Economy ticket for £219 per person are available. Travel duration is 14h 29m
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Alaska Airlines14h 34m014:10Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center05:44Boston Logan AirportBoston Logan Airport0EconomyA Flight from Alaska Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 08/06/2026 14:10:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 09/06/2026 05:44:00. 50 Economy ticket for £254 per person are available. Travel duration is 14h 34m
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FlixBus25h 35m019:15ChicagoDowntown Coach Station21:50Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 08/06/2026 19:15:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 09/06/2026 21:50:00. 50 Economy ticket for £77 per person are available. Travel duration is 25h 35m
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Greyhound US27h 25m007:00ChicagoDowntown Coach Station11:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 08/06/2026 07:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 09/06/2026 11:25:00. 50 Economy ticket for £78 per person are available. Travel duration is 27h 25m
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Greyhound US23h 25m018:00ChicagoDowntown Coach Station18:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 08/06/2026 18:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 09/06/2026 18:25:00. 50 Economy ticket for £78 per person are available. Travel duration is 23h 25m
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Greyhound US33h 15m023:10ChicagoCanal & Van Buren09:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Canal & Van Buren, Chicago (USA) at 08/06/2026 23:10:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 10/06/2026 09:25:00. 50 Economy ticket for £78 per person are available. Travel duration is 33h 15m
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FlixBus25h 35m019:15ChicagoDowntown Coach Station21:50Boston, MASouth Station0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 08/06/2026 19:15:00 to South Station, Boston, MA (USA) arriving at 09/06/2026 21:50:00. 50 Economy ticket for £78 per person are available. Travel duration is 25h 35m
Cheapest Flights Monday
Cheapest Buses Monday
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Greyhound US23h 25m018:00ChicagoDowntown Coach Station18:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 09/06/2026 18:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 10/06/2026 18:25:00. 50 Economy ticket for £59 per person are available. Travel duration is 23h 25m
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FlixBus23h 30m012:25ChicagoDowntown Coach Station12:55Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 09/06/2026 12:25:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 10/06/2026 12:55:00. 50 Economy ticket for £59 per person are available. Travel duration is 23h 30m
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Greyhound US27h 25m007:00ChicagoDowntown Coach Station11:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 09/06/2026 07:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 10/06/2026 11:25:00. 50 Economy ticket for £60 per person are available. Travel duration is 27h 25m
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FlixBus23h 30m012:25ChicagoDowntown Coach Station12:55Boston, MASouth Station0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 09/06/2026 12:25:00 to South Station, Boston, MA (USA) arriving at 10/06/2026 12:55:00. 50 Economy ticket for £60 per person are available. Travel duration is 23h 30m
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Greyhound US27h 25m007:00ChicagoDowntown Coach Station11:25Boston, MASouth Station0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 09/06/2026 07:00:00 to South Station, Boston, MA (USA) arriving at 10/06/2026 11:25:00. 50 Economy ticket for £61 per person are available. Travel duration is 27h 25m
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Frontier Airlines18h 27m006:00Chicago Midway AirportChicago Midway Airport01:27Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 09/06/2026 06:00:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 10/06/2026 01:27:00. 50 Economy ticket for £59 per person are available. Travel duration is 18h 27m
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Frontier Airlines17h 32m006:55Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center01:27Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 09/06/2026 06:55:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 10/06/2026 01:27:00. 50 Economy ticket for £59 per person are available. Travel duration is 17h 32m
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JetBlue Airways2h 29m020:30Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center23:59Boston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 09/06/2026 20:30:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 09/06/2026 23:59:00. 50 Economy ticket for £67 per person are available. Travel duration is 2h 29m
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United Airlines2h 24m006:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center09:29Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 09/06/2026 06:05:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 09/06/2026 09:29:00. 50 Economy ticket for £69 per person are available. Travel duration is 2h 24m
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United Airlines2h 32m007:33Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center11:05Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 09/06/2026 07:33:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 09/06/2026 11:05:00. 50 Economy ticket for £69 per person are available. Travel duration is 2h 32m
Cheapest Buses Tuesday
Cheapest Flights Tuesday
What are the fastest trips from Chicago to Boston, MA?
You can get to Boston, MA from Chicago in just 2h 24m with a Flight from United Airlines. 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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United Airlines2h 35m015:55Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center19:30Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 03/06/2026 15:55:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 03/06/2026 19:30:00. 50 Economy ticket for £61 per person are available. Travel duration is 2h 35m
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United Airlines2h 36m019:45Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center23:21Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 03/06/2026 19:45:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 03/06/2026 23:21:00. 50 Economy ticket for £61 per person are available. Travel duration is 2h 36m
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JetBlue Airways7h 32m015:27Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center23:59Boston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 03/06/2026 15:27:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 03/06/2026 23:59:00. 50 Economy ticket for £122 per person are available. Travel duration is 7h 32m
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Frontier Airlines12h 20m012:04Chicago Midway AirportChicago Midway Airport01:24Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 03/06/2026 12:04:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 04/06/2026 01:24:00. 50 Economy ticket for £70 per person are available. Travel duration is 12h 20m
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Frontier Airlines18h 45m012:04Chicago Midway AirportChicago Midway Airport07:49Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 03/06/2026 12:04:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 04/06/2026 07:49:00. 50 Economy ticket for £80 per person are available. Travel duration is 18h 45m
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FlixBus25h 10m019:40Chicago95th Red Line Station21:50Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 03/06/2026 19:40:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 04/06/2026 21:50:00. 50 Economy ticket for £126 per person are available. Travel duration is 25h 10m
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FlixBus25h 35m019:15ChicagoDowntown Coach Station21:50Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 03/06/2026 19:15:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 04/06/2026 21:50:00. 50 Economy ticket for £114 per person are available. Travel duration is 25h 35m
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Greyhound US32h 50m023:10ChicagoUnion Station09:00Boston, MAAllston0EconomyA Bus from Greyhound US goes from Union Station, Chicago (USA) at 03/06/2026 23:10:00 to Allston, Boston, MA (USA) arriving at 05/06/2026 09:00:00. 50 Economy ticket for £118 per person are available. Travel duration is 32h 50m
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Greyhound US33h 10m022:50ChicagoDowntown Coach Station09:00Boston, MAAllston0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 03/06/2026 22:50:00 to Allston, Boston, MA (USA) arriving at 05/06/2026 09:00:00. 50 Economy ticket for £118 per person are available. Travel duration is 33h 10m
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Greyhound US33h 15m023:10ChicagoUnion Station09:25Boston, MASouth Station0EconomyA Bus from Greyhound US goes from Union Station, Chicago (USA) at 03/06/2026 23:10:00 to South Station, Boston, MA (USA) arriving at 05/06/2026 09:25:00. 50 Economy ticket for £118 per person are available. Travel duration is 33h 15m
Fastest Flights Wednesday
Fastest Buses Wednesday
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United Airlines2h 24m006:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center09:29Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 04/06/2026 06:05:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 04/06/2026 09:29:00. 50 Economy ticket for £66 per person are available. Travel duration is 2h 24m
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JetBlue Airways2h 29m020:30Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center23:59Boston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 04/06/2026 20:30:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 04/06/2026 23:59:00. 50 Economy ticket for £72 per person are available. Travel duration is 2h 29m
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Sun Country Airlines14h 8m018:25Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center09:33Boston Logan AirportBoston Logan Airport0EconomyA Flight from Sun Country Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 04/06/2026 18:25:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 05/06/2026 09:33:00. 50 Economy ticket for £178 per person are available. Travel duration is 14h 8m
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Alaska Airlines14h 34m014:10Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center05:44Boston Logan AirportBoston Logan Airport0EconomyA Flight from Alaska Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 04/06/2026 14:10:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 05/06/2026 05:44:00. 50 Economy ticket for £269 per person are available. Travel duration is 14h 34m
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Frontier Airlines17h 29m006:55Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center01:24Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 04/06/2026 06:55:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 05/06/2026 01:24:00. 50 Economy ticket for £82 per person are available. Travel duration is 17h 29m
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FlixBus22h 35m012:25ChicagoDowntown Coach Station12:00Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 04/06/2026 12:25:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 05/06/2026 12:00:00. 50 Economy ticket for £67 per person are available. Travel duration is 22h 35m
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Greyhound US23h 25m018:00ChicagoDowntown Coach Station18:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 04/06/2026 18:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 05/06/2026 18:25:00. 50 Economy ticket for £66 per person are available. Travel duration is 23h 25m
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FlixBus23h 55m011:05Chicago95th Red Line Station12:00Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 04/06/2026 11:05:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 05/06/2026 12:00:00. 50 Economy ticket for £70 per person are available. Travel duration is 23h 55m
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FlixBus25h 35m019:15ChicagoDowntown Coach Station21:50Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 04/06/2026 19:15:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 05/06/2026 21:50:00. 50 Economy ticket for £66 per person are available. Travel duration is 25h 35m
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Greyhound US27h 25m007:00ChicagoDowntown Coach Station11:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 04/06/2026 07:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 05/06/2026 11:25:00. 50 Economy ticket for £69 per person are available. Travel duration is 27h 25m
Fastest Flights Thursday
Fastest Buses Thursday
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JetBlue Airways2h 29m020:30Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center23:59Boston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 05/06/2026 20:30:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 05/06/2026 23:59:00. 50 Economy ticket for £64 per person are available. Travel duration is 2h 29m
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United Airlines2h 36m018:20Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center21:56Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 05/06/2026 18:20:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 05/06/2026 21:56:00. 50 Economy ticket for £65 per person are available. Travel duration is 2h 36m
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Allegiant Air11h 41m021:23Chicago Midway AirportChicago Midway Airport10:04Boston Logan AirportBoston Logan Airport0EconomyA Flight from Allegiant Air goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 05/06/2026 21:23:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 06/06/2026 10:04:00. 50 Economy ticket for £99 per person are available. Travel duration is 11h 41m
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Frontier Airlines12h 20m012:04Chicago Midway AirportChicago Midway Airport01:24Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 05/06/2026 12:04:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 06/06/2026 01:24:00. 50 Economy ticket for £89 per person are available. Travel duration is 12h 20m
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Sun Country Airlines15h 13m018:25Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center10:38Boston Logan AirportBoston Logan Airport0EconomyA Flight from Sun Country Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 05/06/2026 18:25:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 06/06/2026 10:38:00. 50 Economy ticket for £184 per person are available. Travel duration is 15h 13m
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FlixBus22h 35m012:25ChicagoDowntown Coach Station12:00Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 05/06/2026 12:25:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 06/06/2026 12:00:00. 50 Economy ticket for £122 per person are available. Travel duration is 22h 35m
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FlixBus22h 35m012:25ChicagoDowntown Coach Station12:00Boston, MASouth Station0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 05/06/2026 12:25:00 to South Station, Boston, MA (USA) arriving at 06/06/2026 12:00:00. 50 Economy ticket for £125 per person are available. Travel duration is 22h 35m
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Greyhound US23h 25m018:00ChicagoDowntown Coach Station18:25Boston, MASouth Station0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 05/06/2026 18:00:00 to South Station, Boston, MA (USA) arriving at 06/06/2026 18:25:00. 50 Economy ticket for £124 per person are available. Travel duration is 23h 25m
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Greyhound US23h 25m018:00ChicagoDowntown Coach Station18:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 05/06/2026 18:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 06/06/2026 18:25:00. 50 Economy ticket for £124 per person are available. Travel duration is 23h 25m
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Greyhound US27h 25m007:00ChicagoDowntown Coach Station11:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 05/06/2026 07:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 06/06/2026 11:25:00. 50 Economy ticket for £123 per person are available. Travel duration is 27h 25m
Fastest Flights Friday
Fastest Buses Friday
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JetBlue Airways2h 29m013:55Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center17:24Boston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 06/06/2026 13:55:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 06/06/2026 17:24:00. 50 Economy ticket for £97 per person are available. Travel duration is 2h 29m
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United Airlines2h 34m013:55Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center17:29Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 06/06/2026 13:55:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 06/06/2026 17:29:00. 50 Economy ticket for £72 per person are available. Travel duration is 2h 34m
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United Airlines2h 35m015:55Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center19:30Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 06/06/2026 15:55:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 06/06/2026 19:30:00. 50 Economy ticket for £72 per person are available. Travel duration is 2h 35m
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Frontier Airlines10h 55m013:29Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center01:24Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 06/06/2026 13:29:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 07/06/2026 01:24:00. 50 Economy ticket for £84 per person are available. Travel duration is 10h 55m
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Frontier Airlines12h 25m011:59Chicago Midway AirportChicago Midway Airport01:24Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 06/06/2026 11:59:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 07/06/2026 01:24:00. 50 Economy ticket for £84 per person are available. Travel duration is 12h 25m
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Greyhound US23h 25m018:00ChicagoDowntown Coach Station18:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 06/06/2026 18:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 07/06/2026 18:25:00. 50 Economy ticket for £112 per person are available. Travel duration is 23h 25m
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FlixBus25h 35m019:15ChicagoDowntown Coach Station21:50Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 06/06/2026 19:15:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 07/06/2026 21:50:00. 50 Economy ticket for £113 per person are available. Travel duration is 25h 35m
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Greyhound US27h 25m007:00ChicagoDowntown Coach Station11:25Boston, MASouth Station0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 06/06/2026 07:00:00 to South Station, Boston, MA (USA) arriving at 07/06/2026 11:25:00. 50 Economy ticket for £95 per person are available. Travel duration is 27h 25m
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Greyhound US27h 25m007:00ChicagoDowntown Coach Station11:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 06/06/2026 07:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 07/06/2026 11:25:00. 50 Economy ticket for £95 per person are available. Travel duration is 27h 25m
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FlixBus33h 25m019:15ChicagoDowntown Coach Station05:40Boston, MAAllston0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 06/06/2026 19:15:00 to Allston, Boston, MA (USA) arriving at 08/06/2026 05:40:00. 50 Economy ticket for £106 per person are available. Travel duration is 33h 25m
Fastest Flights Saturday
Fastest Buses Saturday
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United Airlines2h 24m006:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center09:29Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 07/06/2026 06:05:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 07/06/2026 09:29:00. 50 Economy ticket for £88 per person are available. Travel duration is 2h 24m
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JetBlue Airways2h 30m008:49Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center12:19Boston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 07/06/2026 08:49:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 07/06/2026 12:19:00. 50 Economy ticket for £234 per person are available. Travel duration is 2h 30m
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Sun Country Airlines15h 17m018:39Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center10:56Boston Logan AirportBoston Logan Airport0EconomyA Flight from Sun Country Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 07/06/2026 18:39:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 08/06/2026 10:56:00. 50 Economy ticket for £213 per person are available. Travel duration is 15h 17m
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Alaska Airlines19h 44m009:00Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center05:44Boston Logan AirportBoston Logan Airport0EconomyA Flight from Alaska Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 07/06/2026 09:00:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 08/06/2026 05:44:00. 50 Economy ticket for £255 per person are available. Travel duration is 19h 44m
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Frontier Airlines24h 49m006:00Chicago Midway AirportChicago Midway Airport07:49Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 07/06/2026 06:00:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 08/06/2026 07:49:00. 50 Economy ticket for £170 per person are available. Travel duration is 24h 49m
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FlixBus22h 35m012:25ChicagoDowntown Coach Station12:00Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 07/06/2026 12:25:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 08/06/2026 12:00:00. 50 Economy ticket for £105 per person are available. Travel duration is 22h 35m
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FlixBus23h 55m011:05Chicago95th Red Line Station12:00Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from 95th Red Line Station, Chicago (USA) at 07/06/2026 11:05:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 08/06/2026 12:00:00. 50 Economy ticket for £118 per person are available. Travel duration is 23h 55m
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Greyhound US32h 50m023:10ChicagoUnion Station09:00Boston, MAAllston0EconomyA Bus from Greyhound US goes from Union Station, Chicago (USA) at 07/06/2026 23:10:00 to Allston, Boston, MA (USA) arriving at 09/06/2026 09:00:00. 50 Economy ticket for £111 per person are available. Travel duration is 32h 50m
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Greyhound US33h 15m023:10ChicagoCanal & Van Buren09:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Canal & Van Buren, Chicago (USA) at 07/06/2026 23:10:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 09/06/2026 09:25:00. 50 Economy ticket for £108 per person are available. Travel duration is 33h 15m
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Greyhound US33h 15m023:10ChicagoUnion Station09:25Boston, MASouth Station0EconomyA Bus from Greyhound US goes from Union Station, Chicago (USA) at 07/06/2026 23:10:00 to South Station, Boston, MA (USA) arriving at 09/06/2026 09:25:00. 50 Economy ticket for £111 per person are available. Travel duration is 33h 15m
Fastest Flights Sunday
Fastest Buses Sunday
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JetBlue Airways2h 29m020:30Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center23:59Boston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 08/06/2026 20:30:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 08/06/2026 23:59:00. 50 Economy ticket for £82 per person are available. Travel duration is 2h 29m
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United Airlines2h 33m021:41Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center01:14Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 08/06/2026 21:41:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 09/06/2026 01:14:00. 50 Economy ticket for £72 per person are available. Travel duration is 2h 33m
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Sun Country Airlines14h 29m019:09Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center10:38Boston Logan AirportBoston Logan Airport0EconomyA Flight from Sun Country Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 08/06/2026 19:09:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 09/06/2026 10:38:00. 50 Economy ticket for £219 per person are available. Travel duration is 14h 29m
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Alaska Airlines14h 34m014:10Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center05:44Boston Logan AirportBoston Logan Airport0EconomyA Flight from Alaska Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 08/06/2026 14:10:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 09/06/2026 05:44:00. 50 Economy ticket for £254 per person are available. Travel duration is 14h 34m
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Frontier Airlines18h 48m012:04Chicago Midway AirportChicago Midway Airport07:52Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 08/06/2026 12:04:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 09/06/2026 07:52:00. 50 Economy ticket for £118 per person are available. Travel duration is 18h 48m
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Greyhound US23h 25m018:00ChicagoDowntown Coach Station18:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 08/06/2026 18:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 09/06/2026 18:25:00. 50 Economy ticket for £78 per person are available. Travel duration is 23h 25m
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FlixBus25h 35m019:15ChicagoDowntown Coach Station21:50Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 08/06/2026 19:15:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 09/06/2026 21:50:00. 50 Economy ticket for £77 per person are available. Travel duration is 25h 35m
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FlixBus25h 35m019:15ChicagoDowntown Coach Station21:50Boston, MASouth Station0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 08/06/2026 19:15:00 to South Station, Boston, MA (USA) arriving at 09/06/2026 21:50:00. 50 Economy ticket for £78 per person are available. Travel duration is 25h 35m
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Greyhound US27h 25m007:00ChicagoDowntown Coach Station11:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 08/06/2026 07:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 09/06/2026 11:25:00. 50 Economy ticket for £78 per person are available. Travel duration is 27h 25m
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Greyhound US33h 15m023:10ChicagoCanal & Van Buren09:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Canal & Van Buren, Chicago (USA) at 08/06/2026 23:10:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 10/06/2026 09:25:00. 50 Economy ticket for £78 per person are available. Travel duration is 33h 15m
Fastest Flights Monday
Fastest Buses Monday
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United Airlines2h 24m006:05Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center09:29Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 09/06/2026 06:05:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 09/06/2026 09:29:00. 50 Economy ticket for £69 per person are available. Travel duration is 2h 24m
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JetBlue Airways2h 29m020:30Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center23:59Boston Logan AirportBoston Logan Airport0EconomyA Flight from JetBlue Airways goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 09/06/2026 20:30:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 09/06/2026 23:59:00. 50 Economy ticket for £67 per person are available. Travel duration is 2h 29m
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United Airlines2h 32m007:33Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center11:05Boston Logan AirportBoston Logan Airport0EconomyA Flight from United Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 09/06/2026 07:33:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 09/06/2026 11:05:00. 50 Economy ticket for £69 per person are available. Travel duration is 2h 32m
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Frontier Airlines17h 32m006:55Chicago O'Hare AirportChicago O'Hare Airport - Bus/Shuttle Center01:27Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago O'Hare Airport - Bus/Shuttle Center, Chicago O'Hare Airport (USA) at 09/06/2026 06:55:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 10/06/2026 01:27:00. 50 Economy ticket for £59 per person are available. Travel duration is 17h 32m
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Frontier Airlines18h 27m006:00Chicago Midway AirportChicago Midway Airport01:27Boston Logan AirportBoston Logan Airport0EconomyA Flight from Frontier Airlines goes from Chicago Midway Airport, Chicago Midway Airport (USA) at 09/06/2026 06:00:00 to Boston Logan Airport, Boston Logan Airport (USA) arriving at 10/06/2026 01:27:00. 50 Economy ticket for £59 per person are available. Travel duration is 18h 27m
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Greyhound US23h 25m018:00ChicagoDowntown Coach Station18:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 09/06/2026 18:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 10/06/2026 18:25:00. 50 Economy ticket for £59 per person are available. Travel duration is 23h 25m
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FlixBus23h 30m012:25ChicagoDowntown Coach Station12:55Boston, MAAtlantic and Beach St0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 09/06/2026 12:25:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 10/06/2026 12:55:00. 50 Economy ticket for £59 per person are available. Travel duration is 23h 30m
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FlixBus23h 30m012:25ChicagoDowntown Coach Station12:55Boston, MASouth Station0EconomyA Bus from FlixBus goes from Downtown Coach Station, Chicago (USA) at 09/06/2026 12:25:00 to South Station, Boston, MA (USA) arriving at 10/06/2026 12:55:00. 50 Economy ticket for £60 per person are available. Travel duration is 23h 30m
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Greyhound US27h 25m007:00ChicagoDowntown Coach Station11:25Boston, MAAtlantic and Beach St0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 09/06/2026 07:00:00 to Atlantic and Beach St, Boston, MA (USA) arriving at 10/06/2026 11:25:00. 50 Economy ticket for £60 per person are available. Travel duration is 27h 25m
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Greyhound US27h 25m007:00ChicagoDowntown Coach Station11:25Boston, MASouth Station0EconomyA Bus from Greyhound US goes from Downtown Coach Station, Chicago (USA) at 09/06/2026 07:00:00 to South Station, Boston, MA (USA) arriving at 10/06/2026 11:25:00. 50 Economy ticket for £61 per person are available. Travel duration is 27h 25m
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Here you will find all operators and timetables for a
Bus from Chicago to Boston, MA
What are the most popular stations in Chicago and Boston, MA?
In Chicago, you will usually depart from California & 35th Street Coach Stop, Downtown Coach Station or 95th Red Line Station, while in Boston, MA you will be arriving at Atlantic and Beach St, South Station or Logan Office Center Coach Stop, but there are many more stops to explore in both locations.
How do I decide? Some tips and tricks from our experience
Are you having trouble deciding on how to get to Boston, MA from Chicago? With 10 connections between 2 Flight and Bus operators, it can be difficult to find the one ride that will make you happy. But we have some tips that can help you make the best informed decision. First of all, the best trip is always the one that meets all your needs, so make a list of all the things that you want from this journey and look for something that will satisfy all of them. Here we will go through some of the factors mostly commonly taken into consideration.
Look for the lowest price
Ticket price is usually the main concern: even if you can afford to pay more, why do it if there are cheaper options? Saving on the trip means that you can spend more on the vacation itself! Between Chicago and Boston, MA, you can pay as low as £59 with a Bus from Greyhound US.Travel duration
Time is also an important factor. An earlier departure may allow you to see a beautiful sunset or relax before an important event. And remember, time is money, so paying more for a shorter trip may be well worth it. For longer distances, flights are without doubt the best options, but be mindful of airport times and possible delays: a high-speed train may end up cheaper and faster! Here the quicker option is definitely the Flight from United Airlines: you will get to Boston, MA in just 2h 24m.Comfort makes all the difference
You should always take into account what your personal travelling preferences are. Is one hand luggage enough, or are you trasporting more? Would you like to have a snack during the journey? Can you relax in a busy compartment, or do you need space for yourself? Even among the same mode of transportation, different companies will offer you varying levels of comfort and amenities. The main operators connecting Chicago and Boston, MA are Greyhound US, FlixBus and United Airlines, but be sure to check what they have to offer!Save money with deals, and always compare
One last tip? Even if you live in Chicago and Boston, MA is your only destination, it may be wise to check the offers from and to nearby cities or, if you are flyng, nearby airports. Check the trips from Cicero, IL or to Boston Logan Airport, and look at flights from Chicago Midway Airport, and landing at Boston Logan Airport. Comparing different routes may allow you to find deals or promotions you were not aware of. Consider also signing up to CheckMyBus to see even more exclusive promotions!Which companies offer a trip from Chicago to Boston, MA?
The most popular companies between Chicago and Boston, MA, are Greyhound US, FlixBus and United Airlines. Be sure to check their seat class offers and the amenities that they provide.
Bus companies: Greyhound US and FlixBus
Airlines: United Airlines, Frontier Airlines, JetBlue Airways and 3 more.
All you need to know when you travel from Chicago to Boston, MA
Check all information on comfort and services on all modes of transports from Chicago to Boston, MA. See which seat classes are available, and what amenities are other advantages offered by the operators on your journey.
FAQs about the trip from Chicago to Boston, MA
How can I reach Boston, MA from Chicago?
Every day, there are on average 10 connections between Flight and Bus, with which you can get to Boston, MA from Chicago.
How far is Boston, MA from Chicago?
The distance between Chicago and Boston, MA is 1,366.8 km.
What is the most ecofriendly mode of transport between Chicago and Boston, MA?
Trains and buses are by far the greenest options, with trains surpassing buses on longer routes. Planes will always be the worst polluters, especially in shorter flights, were the emissions from the takeoff and landing are less offset by the distance.
On this particular route, a bus will emit, per person, a total of 37 kgs of CO2, a train 48 kgs, a car 232 kgs, and a flight 336 kgs.
What is the cheapest mode of transport from Chicago to Boston, MA?
You can get to Boston, MA with just £59 by taking a Bus from Greyhound US.
What is the fastest way to get from Chicago to Boston, MA?
While a plane is travelling fastest boarding and transfer to airport consumes a lot of time. Usually, high speed trains are better than flights if pure train travel time is below 4 hours. For this particular route, you can get to Boston, MA in just 2h 24m with a Flight from United Airlines.
More routes to Chicago and to Boston, MA
Looking for more options? Here you can see the most popular routes to Chicago and to Boston, MA. Simply click on a connection, and you’ll find all the details about the route!
