There are 7 ways to get from Chicago Midway Airport (MDW) to Boston by plane, train (Amtrak), bus (Flixbus), bus, train, or car
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly Chicago Midway International Airport to Boston Logan Airport
best- Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane MDW - BOS
2h 15m$100–500Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train
cheapest- Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane MDW - PVD
- Take the train from TF Green Airport to South Stationtrain
4h 51m$85–385Fly Chicago O'Hare International Airport to Boston Logan Airport
- Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane ORD - BOS
4h 38m$604–1,010Train (Amtrak)
- Take the train from Chicago Union Station to Bostontrain Lake Shore Limited
23h 49m$326–708Bus (Flixbus)
- Take the bus from Chicago to New York Midtownbus FlixBus N2640
- Take the bus from New York Midtown to Bostonbus FlixBus 2610 / ...
27h 14m$186–326Fly Chicago Midway International Airport to Manchester Airport, bus
- Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)plane MDW - MHT
- Take the bus from Boston Manchester Airport to Bostonbus
4h 35m$114–536Drive 981.2 mi
- Drive from Chicago Midway Airport (MDW) to Bostoncar 981.2 mi
16h 56m$180–259
Chicago Midway Airport (MDW) to Boston by subway, bus, and train (Amtrak)
Questions & Answers
The cheapest way to get from Chicago Midway Airport (MDW) to Boston is to drive which costs $170 - $260 and takes 16h 56m.
The fastest way to get from Chicago Midway Airport (MDW) to Boston is to fly which takes 2h 15m and costs $100 - $500.
No, there is no direct bus from Chicago Midway Airport (MDW) station to Boston. However, there are services departing from Midway Orange Line Station and arriving at Boston via Ashland & 59th Street, Chicago and New York Midtown. The journey, including transfers, takes approximately 27h 14m.
No, there is no direct train from Chicago Midway Airport (MDW) to Boston. However, there are services departing from Midway and arriving at Boston via Chicago Union Station. The journey, including transfers, takes approximately 23h 49m.
The distance between Chicago Midway Airport (MDW) and Boston is 862 miles. The road distance is 987 miles.
The best way to get from Chicago Midway Airport (MDW) to Boston without a car is to train which takes 23h 49m and costs $320 - $750.
It takes approximately 2h 15m to fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS), including transfers and time at the airport.
Chicago Midway Airport (MDW) to Boston bus services, operated by Flixbus USA, depart from Chicago station.
Chicago Midway Airport (MDW) to Boston train services, operated by Amtrak, depart from Chicago Union Station.
The best way to get from Chicago Midway Airport (MDW) to Boston is to fly which takes 2h 15m and costs $100 - $500. Alternatively, you can train, which costs $320 - $750 and takes 23h 49m, you could also bus, which costs $180 - $330 and takes 27h 14m.
What companies run services between Chicago Midway Airport (MDW), USA and Boston, MA, USA?
Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS) every 4 hours. Alternatively, Amtrak operates a train from Chicago Union Station to Boston once daily. Tickets cost $320–700 and the journey takes 22h 2m.
- Website
- southwest.com
Flights from Chicago Midway International Airport to Boston Logan Airport
- Ave. Duration
- 2h 20m
- When
- Every day
- Estimated price
- $100–500
Flights from Chicago Midway International Airport to Manchester Airport
- Ave. Duration
- 2h 12m
- When
- Every day
- Estimated price
- $100–550
Flights from Chicago Midway International Airport to Manchester Airport via Baltimore
- Ave. Duration
- 4h 30m
- When
- Every day
- Estimated price
- $120–600
Flights from Chicago Midway International Airport to Manchester Airport via Nashville
- Ave. Duration
- 4h 55m
- When
- Monday, Thursday, and Friday
- Estimated price
- $150–650
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport
- Ave. Duration
- 2h 18m
- When
- Every day
- Estimated price
- $75–370
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport via Baltimore
- Ave. Duration
- 4h 29m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $80–390
Flights from Chicago Midway International Airport to Theodore Francis Green State Airport via Reagan Washington
- Ave. Duration
- 4h 51m
- When
- Monday, Thursday, Friday, Tuesday, Wednesday, and Sunday
- Estimated price
- $80–390
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 36m
- When
- Every day
- Estimated price
- $80–390
- Website
- united.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 36m
- When
- Every day
- Estimated price
- $80–390
- Website
- delta.com
Flights from Chicago Midway International Airport to Boston Logan Airport via Detroit
- Ave. Duration
- 4h 17m
- When
- Every day
- Estimated price
- $100–500
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 35m
- When
- Every day
- Estimated price
- $80–390
- Website
- jetblue.com
Flights from Chicago O'Hare International Airport to Boston Logan Airport
- Ave. Duration
- 2h 29m
- When
- Every day
- Estimated price
- $80–390
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Chicago Union Station to Boston
- Ave. Duration
- 22h 2m
- Frequency
- Once daily
- Estimated price
- $320–700
- Website
- Amtrak
Train from TF Green Airport to South Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $9–16
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–16
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Chicago to New York Midtown
- Ave. Duration
- 19h 45m
- Frequency
- Twice daily
- Estimated price
- $150–260
- Schedules at
- Flixbus USA
Bus from New York Midtown to Boston
- Ave. Duration
- 4h 20m
- Frequency
- Hourly
- Estimated price
- $30–60
- Schedules at
- Flixbus USA
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Boston Manchester Airport to Boston
- Ave. Duration
- 1h 30m
- Frequency
- 4 times a day
- Estimated price
- $7–15
- Website
- Greyhound
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More Questions & Answers
The quickest flight from Chicago Midway International Airport Airport to Boston Logan Airport Airport is the direct flight which takes 2h 15m.
Chicago Midway Airport (MDW) to Boston bus services, operated by Flixbus USA, arrive at New York Midtown station.
Boston is 1h ahead of Chicago Midway Airport (MDW). It is currently 9:44 AM in Chicago Midway Airport (MDW) and 10:44 AM in Boston.
Chicago Midway Airport (MDW) to Boston train services, operated by Amtrak, arrive at Boston station.
Yes, the driving distance between Chicago Midway Airport (MDW) to Boston is 987 miles. It takes approximately 16h 56m to drive from Chicago Midway Airport (MDW) to Boston.
Delta and Southwest Airlines offer flights from Chicago Midway International Airport Airport to Boston Logan Airport Airport.
There are 1507+ hotels available in Boston.