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 £66 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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Greyhound US29h 30m008:55Boston, MAAtlantic and Beach St13:25Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 03/03/2026 08:55:00 to 95th Red Line Station, Chicago (USA) arriving at 04/03/2026 13:25:00. 50 Economy ticket for £85 per person are available. Travel duration is 29h 30m
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Greyhound US31h 50m016:45Boston, MAAtlantic and Beach St23:35Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 03/03/2026 16:45:00 to 95th Red Line Station, Chicago (USA) arriving at 04/03/2026 23:35:00. 50 Economy ticket for £86 per person are available. Travel duration is 31h 50m
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FlixBus32h 50m021:50Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 03/03/2026 21:50:00 to 95th Red Line Station, Chicago (USA) arriving at 05/03/2026 05:40:00. 50 Economy ticket for £86 per person are available. Travel duration is 32h 50m
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Greyhound US26h 5m008:55Boston, MASouth Station10:00ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from South Station, Boston, MA (USA) at 03/03/2026 08:55:00 to Downtown Coach Station, Chicago (USA) arriving at 04/03/2026 10:00:00. 50 Economy ticket for £87 per person are available. Travel duration is 26h 5m
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FlixBus36h 5m020:55Boston, MAAllston08:00ChicagoUnion Station0EconomyA Bus from FlixBus goes from Allston, Boston, MA (USA) at 03/03/2026 20:55:00 to Union Station, Chicago (USA) arriving at 05/03/2026 08:00:00. 50 Economy ticket for £88 per person are available. Travel duration is 36h 5m
Cheapest Buses Tuesday
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Greyhound US28h 25m002:15Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 04/03/2026 02:15:00 to 95th Red Line Station, Chicago (USA) arriving at 05/03/2026 05:40:00. 50 Economy ticket for £66 per person are available. Travel duration is 28h 25m
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Greyhound US29h 30m008:55Boston, MAAtlantic and Beach St13:25Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 04/03/2026 08:55:00 to 95th Red Line Station, Chicago (USA) arriving at 05/03/2026 13:25:00. 50 Economy ticket for £67 per person are available. Travel duration is 29h 30m
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Greyhound US31h 50m016:45Boston, MAAtlantic and Beach St23:35Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 04/03/2026 16:45:00 to 95th Red Line Station, Chicago (USA) arriving at 05/03/2026 23:35:00. 50 Economy ticket for £67 per person are available. Travel duration is 31h 50m
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FlixBus40h 35m021:50Boston, MAAtlantic and Beach St13:25Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 04/03/2026 21:50:00 to 95th Red Line Station, Chicago (USA) arriving at 06/03/2026 13:25:00. 50 Economy ticket for £70 per person are available. Travel duration is 40h 35m
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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 04/03/2026 21:50:00 to Canal & Van Buren, Chicago (USA) arriving at 06/03/2026 08:00:00. 50 Economy ticket for £75 per person are available. Travel duration is 35h 10m
Cheapest Buses Wednesday
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FlixBus31h 20m017:15Boston, MAAtlantic and Beach St23:35Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 05/03/2026 17:15:00 to 95th Red Line Station, Chicago (USA) arriving at 06/03/2026 23:35:00. 50 Economy ticket for £84 per person are available. Travel duration is 31h 20m
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Greyhound US28h 25m002:15Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 05/03/2026 02:15:00 to 95th Red Line Station, Chicago (USA) arriving at 06/03/2026 05:40:00. 50 Economy ticket for £85 per person are available. Travel duration is 28h 25m
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FlixBus31h 20m017:15Boston, MASouth Station23:35Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from South Station, Boston, MA (USA) at 05/03/2026 17:15:00 to 95th Red Line Station, Chicago (USA) arriving at 06/03/2026 23:35:00. 50 Economy ticket for £86 per person are available. Travel duration is 31h 20m
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Greyhound US29h 30m008:55Boston, MAAtlantic and Beach St13:25Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 05/03/2026 08:55:00 to 95th Red Line Station, Chicago (USA) arriving at 06/03/2026 13:25:00. 50 Economy ticket for £86 per person are available. Travel duration is 29h 30m
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FlixBus29h 10m001:30Boston, MAAllston05:40Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Allston, Boston, MA (USA) at 05/03/2026 01:30:00 to 95th Red Line Station, Chicago (USA) arriving at 06/03/2026 05:40:00. 50 Economy ticket for £87 per person are available. Travel duration is 29h 10m
Cheapest Buses Thursday
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FlixBus31h 20m017:15Boston, MAAtlantic and Beach St23:35Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 06/03/2026 17:15:00 to 95th Red Line Station, Chicago (USA) arriving at 07/03/2026 23:35:00. 50 Economy ticket for £103 per person are available. Travel duration is 31h 20m
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Greyhound US28h 25m002:15Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 06/03/2026 02:15:00 to 95th Red Line Station, Chicago (USA) arriving at 07/03/2026 05:40:00. 50 Economy ticket for £103 per person are available. Travel duration is 28h 25m
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Greyhound US29h 30m008:55Boston, MAAtlantic and Beach St13:25Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 06/03/2026 08:55:00 to 95th Red Line Station, Chicago (USA) arriving at 07/03/2026 13:25:00. 50 Economy ticket for £106 per person are available. Travel duration is 29h 30m
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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 06/03/2026 17:15:00 to Downtown Coach Station, Chicago (USA) arriving at 07/03/2026 20:05:00. 50 Economy ticket for £107 per person are available. Travel duration is 27h 50m
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Greyhound US28h 55m002:15Boston, MAAtlantic and Beach St06:10ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 06/03/2026 02:15:00 to Downtown Coach Station, Chicago (USA) arriving at 07/03/2026 06:10:00. 50 Economy ticket for £107 per person are available. Travel duration is 28h 55m
Cheapest Buses Friday
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FlixBus31h 50m021:50Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 07/03/2026 21:50:00 to 95th Red Line Station, Chicago (USA) arriving at 09/03/2026 05:40:00. 50 Economy ticket for £109 per person are available. Travel duration is 31h 50m
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FlixBus30h 20m017:15Boston, MAAtlantic and Beach St23:35Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 07/03/2026 17:15:00 to 95th Red Line Station, Chicago (USA) arriving at 08/03/2026 23:35:00. 50 Economy ticket for £112 per person are available. Travel duration is 30h 20m
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Greyhound US28h 25m002:15Boston, MAAtlantic and Beach St06:40Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 07/03/2026 02:15:00 to 95th Red Line Station, Chicago (USA) arriving at 08/03/2026 06:40:00. 50 Economy ticket for £114 per person are available. Travel duration is 28h 25m
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Greyhound US28h 30m008:55Boston, MAAtlantic and Beach St13:25Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 07/03/2026 08:55:00 to 95th Red Line Station, Chicago (USA) arriving at 08/03/2026 13:25:00. 50 Economy ticket for £114 per person are available. Travel duration is 28h 30m
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FlixBus30h 20m017:15Boston, MASouth Station23:35Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from South Station, Boston, MA (USA) at 07/03/2026 17:15:00 to 95th Red Line Station, Chicago (USA) arriving at 08/03/2026 23:35:00. 50 Economy ticket for £115 per person are available. Travel duration is 30h 20m
Cheapest Buses Saturday
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Greyhound US27h 45m001:55Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 08/03/2026 01:55:00 to 95th Red Line Station, Chicago (USA) arriving at 09/03/2026 05:40:00. 50 Economy ticket for £114 per person are available. Travel duration is 27h 45m
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FlixBus32h 50m021:50Boston, MASouth Station05:40Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from South Station, Boston, MA (USA) at 08/03/2026 21:50:00 to 95th Red Line Station, Chicago (USA) arriving at 10/03/2026 05:40:00. 50 Economy ticket for £116 per person are available. Travel duration is 32h 50m
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FlixBus32h 50m021:50Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 08/03/2026 21:50:00 to 95th Red Line Station, Chicago (USA) arriving at 10/03/2026 05:40:00. 50 Economy ticket for £116 per person are available. Travel duration is 32h 50m
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Greyhound US27h 45m001:55Boston, MASouth Station05:40Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from South Station, Boston, MA (USA) at 08/03/2026 01:55:00 to 95th Red Line Station, Chicago (USA) arriving at 09/03/2026 05:40:00. 50 Economy ticket for £116 per person are available. Travel duration is 27h 45m
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FlixBus36h 5m020:55Boston, MAAllston08:00ChicagoUnion Station0EconomyA Bus from FlixBus goes from Allston, Boston, MA (USA) at 08/03/2026 20:55:00 to Union Station, Chicago (USA) arriving at 10/03/2026 08:00:00. 50 Economy ticket for £117 per person are available. Travel duration is 36h 5m
Cheapest Buses Sunday
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FlixBus31h 20m017:15Boston, MAAtlantic and Beach St23:35Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 09/03/2026 17:15:00 to 95th Red Line Station, Chicago (USA) arriving at 10/03/2026 23:35:00. 50 Economy ticket for £83 per person are available. Travel duration is 31h 20m
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FlixBus32h 50m021:50Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 09/03/2026 21:50:00 to 95th Red Line Station, Chicago (USA) arriving at 11/03/2026 05:40:00. 50 Economy ticket for £84 per person are available. Travel duration is 32h 50m
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Greyhound US24h 40m006:00Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 09/03/2026 06:00:00 to 95th Red Line Station, Chicago (USA) arriving at 10/03/2026 05:40:00. 50 Economy ticket for £85 per person are available. Travel duration is 24h 40m
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FlixBus31h 20m017:15Boston, MASouth Station23:35Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from South Station, Boston, MA (USA) at 09/03/2026 17:15:00 to 95th Red Line Station, Chicago (USA) arriving at 10/03/2026 23:35:00. 50 Economy ticket for £86 per person are available. Travel duration is 31h 20m
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Greyhound US29h 30m008:55Boston, MAAtlantic and Beach St13:25Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 09/03/2026 08:55:00 to 95th Red Line Station, Chicago (USA) arriving at 10/03/2026 13:25:00. 50 Economy ticket for £87 per person are available. Travel duration is 29h 30m
Cheapest Buses Monday
What are the fastest trips from Boston, MA to Chicago?
You can get to Chicago from Boston, MA in just 24h 40m with a Bus from Greyhound US. 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 US26h 5m008:55Boston, MASouth Station10:00ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from South Station, Boston, MA (USA) at 03/03/2026 08:55:00 to Downtown Coach Station, Chicago (USA) arriving at 04/03/2026 10:00:00. 50 Economy ticket for £87 per person are available. Travel duration is 26h 5m
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Greyhound US29h 30m008:55Boston, MAAtlantic and Beach St13:25Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 03/03/2026 08:55:00 to 95th Red Line Station, Chicago (USA) arriving at 04/03/2026 13:25:00. 50 Economy ticket for £85 per person are available. Travel duration is 29h 30m
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Greyhound US31h 50m016:45Boston, MAAtlantic and Beach St23:35Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 03/03/2026 16:45:00 to 95th Red Line Station, Chicago (USA) arriving at 04/03/2026 23:35:00. 50 Economy ticket for £86 per person are available. Travel duration is 31h 50m
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FlixBus32h 50m021:50Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 03/03/2026 21:50:00 to 95th Red Line Station, Chicago (USA) arriving at 05/03/2026 05:40:00. 50 Economy ticket for £86 per person are available. Travel duration is 32h 50m
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FlixBus36h 5m020:55Boston, MAAllston08:00ChicagoUnion Station0EconomyA Bus from FlixBus goes from Allston, Boston, MA (USA) at 03/03/2026 20:55:00 to Union Station, Chicago (USA) arriving at 05/03/2026 08:00:00. 50 Economy ticket for £88 per person are available. Travel duration is 36h 5m
Fastest Buses Tuesday
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Greyhound US28h 25m002:15Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 04/03/2026 02:15:00 to 95th Red Line Station, Chicago (USA) arriving at 05/03/2026 05:40:00. 50 Economy ticket for £66 per person are available. Travel duration is 28h 25m
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Greyhound US29h 30m008:55Boston, MAAtlantic and Beach St13:25Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 04/03/2026 08:55:00 to 95th Red Line Station, Chicago (USA) arriving at 05/03/2026 13:25:00. 50 Economy ticket for £67 per person are available. Travel duration is 29h 30m
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Greyhound US31h 50m016:45Boston, MAAtlantic and Beach St23:35Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 04/03/2026 16:45:00 to 95th Red Line Station, Chicago (USA) arriving at 05/03/2026 23:35:00. 50 Economy ticket for £67 per person are available. Travel duration is 31h 50m
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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 04/03/2026 21:50:00 to Canal & Van Buren, Chicago (USA) arriving at 06/03/2026 08:00:00. 50 Economy ticket for £75 per person are available. Travel duration is 35h 10m
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FlixBus40h 35m021:50Boston, MAAtlantic and Beach St13:25Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 04/03/2026 21:50:00 to 95th Red Line Station, Chicago (USA) arriving at 06/03/2026 13:25:00. 50 Economy ticket for £70 per person are available. Travel duration is 40h 35m
Fastest Buses Wednesday
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Greyhound US28h 25m002:15Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 05/03/2026 02:15:00 to 95th Red Line Station, Chicago (USA) arriving at 06/03/2026 05:40:00. 50 Economy ticket for £85 per person are available. Travel duration is 28h 25m
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FlixBus29h 10m001:30Boston, MAAllston05:40Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Allston, Boston, MA (USA) at 05/03/2026 01:30:00 to 95th Red Line Station, Chicago (USA) arriving at 06/03/2026 05:40:00. 50 Economy ticket for £87 per person are available. Travel duration is 29h 10m
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Greyhound US29h 30m008:55Boston, MAAtlantic and Beach St13:25Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 05/03/2026 08:55:00 to 95th Red Line Station, Chicago (USA) arriving at 06/03/2026 13:25:00. 50 Economy ticket for £86 per person are available. Travel duration is 29h 30m
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FlixBus31h 20m017:15Boston, MAAtlantic and Beach St23:35Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 05/03/2026 17:15:00 to 95th Red Line Station, Chicago (USA) arriving at 06/03/2026 23:35:00. 50 Economy ticket for £84 per person are available. Travel duration is 31h 20m
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FlixBus31h 20m017:15Boston, MASouth Station23:35Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from South Station, Boston, MA (USA) at 05/03/2026 17:15:00 to 95th Red Line Station, Chicago (USA) arriving at 06/03/2026 23:35:00. 50 Economy ticket for £86 per person are available. Travel duration is 31h 20m
Fastest Buses Thursday
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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 06/03/2026 17:15:00 to Downtown Coach Station, Chicago (USA) arriving at 07/03/2026 20:05:00. 50 Economy ticket for £107 per person are available. Travel duration is 27h 50m
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Greyhound US28h 25m002:15Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 06/03/2026 02:15:00 to 95th Red Line Station, Chicago (USA) arriving at 07/03/2026 05:40:00. 50 Economy ticket for £103 per person are available. Travel duration is 28h 25m
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Greyhound US28h 55m002:15Boston, MAAtlantic and Beach St06:10ChicagoDowntown Coach Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 06/03/2026 02:15:00 to Downtown Coach Station, Chicago (USA) arriving at 07/03/2026 06:10:00. 50 Economy ticket for £107 per person are available. Travel duration is 28h 55m
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Greyhound US29h 30m008:55Boston, MAAtlantic and Beach St13:25Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 06/03/2026 08:55:00 to 95th Red Line Station, Chicago (USA) arriving at 07/03/2026 13:25:00. 50 Economy ticket for £106 per person are available. Travel duration is 29h 30m
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FlixBus31h 20m017:15Boston, MAAtlantic and Beach St23:35Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 06/03/2026 17:15:00 to 95th Red Line Station, Chicago (USA) arriving at 07/03/2026 23:35:00. 50 Economy ticket for £103 per person are available. Travel duration is 31h 20m
Fastest Buses Friday
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Greyhound US28h 25m002:15Boston, MAAtlantic and Beach St06:40Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 07/03/2026 02:15:00 to 95th Red Line Station, Chicago (USA) arriving at 08/03/2026 06:40:00. 50 Economy ticket for £114 per person are available. Travel duration is 28h 25m
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Greyhound US28h 30m008:55Boston, MAAtlantic and Beach St13:25Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 07/03/2026 08:55:00 to 95th Red Line Station, Chicago (USA) arriving at 08/03/2026 13:25:00. 50 Economy ticket for £114 per person are available. Travel duration is 28h 30m
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FlixBus30h 20m017:15Boston, MAAtlantic and Beach St23:35Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 07/03/2026 17:15:00 to 95th Red Line Station, Chicago (USA) arriving at 08/03/2026 23:35:00. 50 Economy ticket for £112 per person are available. Travel duration is 30h 20m
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FlixBus30h 20m017:15Boston, MASouth Station23:35Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from South Station, Boston, MA (USA) at 07/03/2026 17:15:00 to 95th Red Line Station, Chicago (USA) arriving at 08/03/2026 23:35:00. 50 Economy ticket for £115 per person are available. Travel duration is 30h 20m
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FlixBus31h 50m021:50Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 07/03/2026 21:50:00 to 95th Red Line Station, Chicago (USA) arriving at 09/03/2026 05:40:00. 50 Economy ticket for £109 per person are available. Travel duration is 31h 50m
Fastest Buses Saturday
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Greyhound US27h 45m001:55Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 08/03/2026 01:55:00 to 95th Red Line Station, Chicago (USA) arriving at 09/03/2026 05:40:00. 50 Economy ticket for £114 per person are available. Travel duration is 27h 45m
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Greyhound US27h 45m001:55Boston, MASouth Station05:40Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from South Station, Boston, MA (USA) at 08/03/2026 01:55:00 to 95th Red Line Station, Chicago (USA) arriving at 09/03/2026 05:40:00. 50 Economy ticket for £116 per person are available. Travel duration is 27h 45m
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FlixBus32h 50m021:50Boston, MASouth Station05:40Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from South Station, Boston, MA (USA) at 08/03/2026 21:50:00 to 95th Red Line Station, Chicago (USA) arriving at 10/03/2026 05:40:00. 50 Economy ticket for £116 per person are available. Travel duration is 32h 50m
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FlixBus32h 50m021:50Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 08/03/2026 21:50:00 to 95th Red Line Station, Chicago (USA) arriving at 10/03/2026 05:40:00. 50 Economy ticket for £116 per person are available. Travel duration is 32h 50m
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FlixBus36h 5m020:55Boston, MAAllston08:00ChicagoUnion Station0EconomyA Bus from FlixBus goes from Allston, Boston, MA (USA) at 08/03/2026 20:55:00 to Union Station, Chicago (USA) arriving at 10/03/2026 08:00:00. 50 Economy ticket for £117 per person are available. Travel duration is 36h 5m
Fastest Buses Sunday
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Greyhound US24h 40m006:00Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 09/03/2026 06:00:00 to 95th Red Line Station, Chicago (USA) arriving at 10/03/2026 05:40:00. 50 Economy ticket for £85 per person are available. Travel duration is 24h 40m
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Greyhound US29h 30m008:55Boston, MAAtlantic and Beach St13:25Chicago95th Red Line Station0EconomyA Bus from Greyhound US goes from Atlantic and Beach St, Boston, MA (USA) at 09/03/2026 08:55:00 to 95th Red Line Station, Chicago (USA) arriving at 10/03/2026 13:25:00. 50 Economy ticket for £87 per person are available. Travel duration is 29h 30m
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FlixBus31h 20m017:15Boston, MAAtlantic and Beach St23:35Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 09/03/2026 17:15:00 to 95th Red Line Station, Chicago (USA) arriving at 10/03/2026 23:35:00. 50 Economy ticket for £83 per person are available. Travel duration is 31h 20m
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FlixBus31h 20m017:15Boston, MASouth Station23:35Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from South Station, Boston, MA (USA) at 09/03/2026 17:15:00 to 95th Red Line Station, Chicago (USA) arriving at 10/03/2026 23:35:00. 50 Economy ticket for £86 per person are available. Travel duration is 31h 20m
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FlixBus32h 50m021:50Boston, MAAtlantic and Beach St05:40Chicago95th Red Line Station0EconomyA Bus from FlixBus goes from Atlantic and Beach St, Boston, MA (USA) at 09/03/2026 21:50:00 to 95th Red Line Station, Chicago (USA) arriving at 11/03/2026 05:40:00. 50 Economy ticket for £84 per person are available. Travel duration is 32h 50m
Fastest Buses Monday
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 Logan Office Center Coach Stop, 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 5 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 £66 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 Bus from Greyhound US: you will get to Chicago in just 24h 40m.Comfort makes all the difference
You should always take into account what your personal travelling preferences are. Is one hand luggage enough, or are you trasporting more? Would you like to have a snack during the journey? Can you relax in a busy compartment, or do you need space for yourself? Even among the same mode of transportation, different companies will offer you varying levels of comfort and amenities. The main operators connecting Boston, MA and Chicago are FlixBus and Greyhound US, 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 FlixBus and Greyhound US. Be sure to check their seat class offers and the amenities that they provide.
Bus companies: FlixBus and Greyhound US
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 5 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 £66 by taking a Bus from Greyhound US.
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 24h 40m with a Bus from Greyhound US.
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
- Atlanta, GA to Boston, MA
- Baltimore, MD to Boston, MA
- Montreal to Boston, MA
- New York to Boston, MA
- Newark to Boston, MA
- Norfolk, VA to Boston, MA
- Ottawa, ON to Boston, MA
- Philadelphia, PA to Boston, MA
- Raleigh, NC to Boston, MA
- Syracuse, NY to Boston, MA
- Toronto, ON to Boston, MA
- Washington, DC to Boston, MA
- Trips to Chicago
- Atlanta, GA to Chicago
- Cincinnati to Chicago
- Dallas to Chicago
- El Paso, TX to Chicago
- Houston to Chicago
- Little Rock, AR to Chicago
- Memphis to Chicago
- Mississauga, ON to Chicago
- Monterrey, NL to Chicago
- Nashville to Chicago
- New York to Chicago
- Oklahoma City, OK to Chicago
- Pearson Toronto Airport to Chicago
- Philadelphia, PA to Chicago
- Pittsburgh to Chicago
- San Antonio, TX to Chicago
- St. Louis, MO to Chicago
- Tampa to Chicago
- Toronto, ON to Chicago
- Tulsa to Chicago
