There are 10 ways to get from Boston to Chicago Union Station by plane, train (Amtrak), bus (Greyhound, Flixbus), car, bus, 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 Boston Logan Airport to Chicago Midway International Airport
best- Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane BOS - MDW
3h 26m$88–439Train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport
cheapest- Take the train from South Station to TF Green Airporttrain
- Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane PVD - ORD
6h 2m$77–361Train (Amtrak)
- Take the train from Boston to Chicago Union Stationtrain Lake Shore Limited
22h 22m$260–600Bus
- Take the bus from Boston to Newark Penn Stationbus Greyhound US0235 / ...
- Take the bus from Newark Penn Station to Chicago Bus Stationbus FlixBus N2640 / ...
26h 9m$168–273Drive 980.6 mi
- Drive from Boston to Chicago Union Stationcar 980.6 mi
16h 49m$179–259Fly Boston Logan Airport to Chicago O'Hare International Airport
- Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane BOS - ORD
3h 45m$606–892Bus to Manchester Airport, fly to Chicago Midway International Airport
- Take the bus from Boston to Boston Manchester Airportbus
- Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane MHT - MDW
5h 21m$130–667Train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport
- Take the train from South Station to TF Green Airporttrain
- Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane PVD - MDW
5h 53m$92–431Bus to Manchester Airport, fly to Chicago O'Hare International Airport
- Take the bus from Boston to Boston Manchester Airportbus
- Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)plane MHT - ORD
5h 56m$110–567Fly Boston Logan Airport 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 to Chicago Union Station by train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Boston to Chicago Union Station is to bus which costs $160 - $280 and takes 26h 9m.
The fastest way to get from Boston to Chicago Union Station is to fly which takes 3h 26m and costs $85 - $440.
No, there is no direct bus from Boston to Chicago Union Station station. However, there are services departing from Boston and arriving at Chicago Bus Station via Newark Penn Station. The journey, including transfers, takes approximately 26h 9m.
Yes, there is a direct train departing from Boston and arriving at Chicago Union Station station. Services depart once daily, and operate every day. The journey takes approximately 22h 22m.
The distance between Boston and Chicago Union Station is 874 miles. The road distance is 986.3 miles.
The best way to get from Boston to Chicago Union Station without a car is to train which takes 22h 22m and costs $260 - $600.
It takes approximately 3h 26m to get from Boston to Chicago Union Station, including transfers.
Boston to Chicago Union Station bus services, operated by Greyhound USA, depart from Boston station.
Boston to Chicago Union Station train services, operated by Amtrak, depart from Boston station.
The best way to get from Boston to Chicago Union Station is to fly which takes 3h 26m and costs $85 - $440. Alternatively, you can train, which costs $260 - $600 and takes 22h 22m, you could also bus, which costs $160 - $280 and takes 26h 9m.
What companies run services between Boston, MA, USA and Chicago Union Station, 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 22m.
- 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 Manchester Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 26m
- When
- Every day
- Estimated price
- $120–650
Flights from Manchester Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 40m
- When
- Every day
- Estimated price
- $130–650
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 29m
- When
- Every day
- Estimated price
- $80–410
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 38m
- When
- Every day
- Estimated price
- $85–430
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 22m
- 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
Bus from Boston to Boston Manchester Airport
- Ave. Duration
- 1h 5m
- Frequency
- Twice daily
- Estimated price
- $7–13
- Website
- Greyhound
Bus from Boston to Boston Manchester Airport
- Ave. Duration
- 1h 5m
- Frequency
- Twice daily
- Estimated price
- $7–13
- Website
- Greyhound
Want to know more about travelling around United States
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Booking & Getting There
Boston to Chicago Union Station bus services, operated by Greyhound USA, arrive at Newark Penn Station.
Chicago Union Station is 1h behind Boston. It is currently 10:35 PM in Boston and 9:35 PM in Chicago Union Station.
Boston to Chicago Union Station train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Boston to Chicago Union Station is 986 miles. It takes approximately 16h 49m to drive from Boston to Chicago Union Station.
Book your Boston to Chicago Union Station train tickets online with Omio.
Book your Boston to Chicago Union Station bus tickets online with Omio and FlixBus.
There are 1279+ hotels available in Chicago Union Station.