There are 6 ways to get from Boston Airport (BOS) to Chicago by plane, train (Amtrak), bus (Greyhound, Flixbus), car, or train
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly to Chicago Midway International Airport
best- Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane BOS - MDW
3h 16m$88–439Train (Amtrak)
- Take the train from Boston to Chicago Union Stationtrain Lake Shore Limited
23h 28m$269–609Bus
- Take the bus from Boston to Newark Penn Stationbus Greyhound US0235 / ...
- Take the bus from Newark Penn Station to Chicago Bus Stationbus FlixBus N2640 / ...
27h 21m$167–279Drive 983.3 mi
- Drive from Boston Airport (BOS) to Chicagocar 983.3 mi
16h 51m$180–260Fly to Chicago O'Hare International Airport
- Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane BOS - ORD
3h 32m$606–892Fly to General Mitchell International Airport, train
- Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane BOS - MKE
- Take the train from Milwaukee to Chicago Union Stationtrain
5h 42m$682–1,891
Boston Airport (BOS) to Chicago by bus and train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Boston Airport (BOS) to Chicago is to bus which costs $160 - $280 and takes 27h 21m.
The fastest way to get from Boston Airport (BOS) to Chicago is to fly which takes 3h 16m and costs $85 - $440.
No, there is no direct bus from Boston Airport (BOS) to Chicago station. However, there are services departing from Terminal C - Arrivals Level and arriving at Chicago Bus Station via Boston and Newark Penn Station. The journey, including transfers, takes approximately 27h 21m.
No, there is no direct train from Boston Airport (BOS) to Chicago station. However, there are services departing from Boston and arriving at Chicago Union Station via . The journey, including transfers, takes approximately 23h 28m.
The distance between Boston Airport (BOS) and Chicago is 873 miles. The road distance is 989 miles.
The best way to get from Boston Airport (BOS) to Chicago without a car is to train which takes 23h 28m and costs $260 - $650.
It takes approximately 3h 16m to get from Boston Airport (BOS) to Chicago, including transfers.
Boston Airport (BOS) to Chicago bus services, operated by Greyhound USA, depart from Boston station.
Boston Airport (BOS) to Chicago train services, operated by Amtrak, depart from Boston station.
The best way to get from Boston Airport (BOS) to Chicago is to fly which takes 3h 16m and costs $85 - $440. Alternatively, you can train, which costs $260 - $650 and takes 23h 28m, you could also bus, which costs $160 - $280 and takes 27h 21m.
What companies run services between Boston Airport (BOS), USA and Chicago, IL, USA?
Southwest Airlines and Delta fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $260–600 and the journey takes 22h 15m.
- Website
- southwest.com
Flights from Boston Logan Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 41m
- When
- Every day
- Estimated price
- $85–440
Flights from Boston Logan Airport to General Mitchell International Airport via Baltimore
- Ave. Duration
- 4h 38m
- When
- Sunday, Tuesday, and Wednesday
- Estimated price
- $140–700
Flights from Boston Logan Airport to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 4h 48m
- When
- Sunday and Saturday
- Estimated price
- $130–700
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Boston to Chicago Union Station
- Ave. Duration
- 22h 15m
- Frequency
- Once daily
- Estimated price
- $260–600
- Website
- Amtrak
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $21–50
- Website
- Amtrak
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Boston to Newark Penn Station
- Ave. Duration
- 5h 20m
- Frequency
- 4 times a day
- Estimated price
- $40–65
- Website
- Greyhound
Want to know more about travelling around United States
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Booking & Getting There
Boston Airport (BOS) to Chicago bus services, operated by Greyhound USA, arrive at Newark Penn Station.
Chicago is 1h behind Boston Airport (BOS). It is currently 11:16 AM in Boston Airport (BOS) and 10:16 AM in Chicago.
Boston Airport (BOS) to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Boston Airport (BOS) to Chicago is 989 miles. It takes approximately 16h 51m to drive from Boston Airport (BOS) to Chicago.
There are 1284+ hotels available in Chicago.