There are 9 ways to get from Boston to Chicago Loop 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 19m$88–447Train 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
5h 47m$72–361Train (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 12m$171–276Drive 980.9 mi
- Drive from Boston to Chicago Loopcar 980.9 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 30m$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 14m$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 47m$92–441Bus 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 41m$105–517
Boston to Chicago Loop by train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Boston to Chicago Loop is to train and fly which costs $70 - $370 and takes 5h 47m.
The fastest way to get from Boston to Chicago Loop is to fly which takes 3h 19m and costs $85 - $450.
No, there is no direct bus from Boston to Chicago Loop. However, there are services departing from Boston and arriving at Washington & Lasalle via Newark Penn Station and Jefferson & Harrison. The journey, including transfers, takes approximately 26h 12m.
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 Loop is 874 miles. The road distance is 986.7 miles.
The best way to get from Boston to Chicago Loop without a car is to train which takes 22h 22m and costs $260 - $600.
It takes approximately 3h 19m to get from Boston to Chicago Loop, including transfers.
Boston to Chicago Loop bus services, operated by Greyhound USA, depart from Boston station.
Boston to Chicago Loop train services, operated by Amtrak, depart from Boston station.
The best way to get from Boston to Chicago Loop is to fly which takes 3h 19m and costs $85 - $450. Alternatively, you can train, which costs $260 - $600 and takes 22h 22m, you could also bus, which costs $170 - $280 and takes 26h 12m.
What companies run services between Boston, MA, USA and Chicago Loop, 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
- aa.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 5m
- When
- Every day
- Estimated price
- $65–360
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 57m
- When
- Every day
- Estimated price
- $60–340
Flights from Theodore Francis Green State Airport to Chicago O'Hare International Airport via Philadelphia
- Ave. Duration
- 5h 7m
- When
- Every day
- Estimated price
- $65–350
Flights from Manchester Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 56m
- When
- Every day
- Estimated price
- $95–500
Flights from Manchester Airport to Chicago O'Hare International Airport via Philadelphia
- Ave. Duration
- 5h 36m
- When
- Every day
- Estimated price
- $100–550
Flights from Manchester Airport to Chicago O'Hare International Airport via Reagan Washington
- Ave. Duration
- 6h
- When
- Every day
- Estimated price
- $100–550
Flights from Manchester Airport to Chicago O'Hare International Airport via Charlotte
- Ave. Duration
- 6h 18m
- When
- Every day
- Estimated price
- $130–650
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
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- 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 Loop bus services, operated by Greyhound USA, arrive at Newark Penn Station.
Chicago Loop is 1h behind Boston. It is currently 1:29 PM in Boston and 12:29 PM in Chicago Loop.
Boston to Chicago Loop train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Boston to Chicago Loop is 987 miles. It takes approximately 16h 49m to drive from Boston to Chicago Loop.
Book your Boston to Chicago Loop train tickets online with Omio.
There are 1285+ hotels available in Chicago Loop.