There are 7 ways to get from Boston to Chicago Midway Airport (MDW) by plane, train (Amtrak), bus (Greyhound, 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 Boston Logan Airport to Chicago Midway International Airport
best- Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane BOS - MDW
2h 30m$85–410Fly 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
4h 5m$623–1,009Train (Amtrak)
- Take the train from Boston to Chicago Union Stationtrain Lake Shore Limited
23h 3m$329–675Bus
- Take the bus from Boston to Newark Penn Stationbus Greyhound US0235 / ...
- Take the bus from Newark Penn Station to Chicago Bus Stationbus FlixBus N2641 / ...
24h 10m$175–300Bus 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
4h 25m$103–484Train 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 2m$85–406Drive 980.3 mi
- Drive from Boston to Chicago Midway Airport (MDW)car 980.3 mi
16h 50m$179–259
Boston to Chicago Midway Airport (MDW) by train, bus, and subway (Amtrak)
Questions & Answers
The cheapest way to get from Boston to Chicago Midway Airport (MDW) is to bus which costs $170 - $300 and takes 24h 10m.
The fastest way to get from Boston to Chicago Midway Airport (MDW) is to fly which takes 2h 30m and costs $85 - $410.
No, there is no direct bus from Boston to Chicago Midway Airport (MDW) station. However, there are services departing from Boston and arriving at Midway Orange Line Station via Newark Penn Station, Harrison & Jefferson and Cicero & 24th Place. The journey, including transfers, takes approximately 24h 10m.
No, there is no direct train from Boston to Chicago Midway Airport (MDW). However, there are services departing from Boston and arriving at Midway via Adams/Wabash. The journey, including transfers, takes approximately 23h 3m.
The distance between Boston and Chicago Midway Airport (MDW) is 862 miles. The road distance is 986.1 miles.
The best way to get from Boston to Chicago Midway Airport (MDW) without a car is to train which takes 23h 3m and costs $320 - $700.
It takes approximately 2h 30m to fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW), including transfers and time at the airport.
Boston to Chicago Midway Airport (MDW) bus services, operated by Greyhound USA, depart from Boston station.
Boston to Chicago Midway Airport (MDW) train services, operated by Amtrak, depart from Boston station.
The best way to get from Boston to Chicago Midway Airport (MDW) is to fly which takes 2h 30m and costs $85 - $410. Alternatively, you can train, which costs $320 - $700 and takes 23h 3m, you could also bus, which costs $170 - $300 and takes 24h 10m.
What companies run services between Boston, MA, USA and Chicago Midway Airport (MDW), 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 $320–700 and the journey takes 22h 22m.
- Website
- southwest.com
Flights from Boston Logan Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 35m
- When
- Every day
- Estimated price
- $85–410
Flights from Manchester Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 21m
- When
- Every day
- Estimated price
- $95–470
Flights from Manchester Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 32m
- When
- Tuesday, Wednesday, Monday, Thursday, Friday, and Sunday
- Estimated price
- $100–500
Flights from Manchester Airport to Chicago Midway International Airport via Nashville
- Ave. Duration
- 5h
- When
- Monday, Thursday, and Friday
- Estimated price
- $130–600
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 25m
- When
- Every day
- Estimated price
- $75–390
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 53m
- When
- Monday, Thursday, Friday, Tuesday, Wednesday, and Sunday
- Estimated price
- $85–410
- Website
- aa.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 8m
- When
- Every day
- Estimated price
- $70–350
- Website
- united.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 56m
- When
- Every day
- Estimated price
- $70–350
- Website
- delta.com
Flights from Boston Logan Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 4h 39m
- When
- Every day
- Estimated price
- $85–410
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 56m
- When
- Every day
- Estimated price
- $70–350
Flights from Theodore Francis Green State Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 4h 32m
- When
- Every day
- Estimated price
- $75–390
- Website
- jetblue.com
Flights from Boston Logan Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h
- When
- Every day
- Estimated price
- $70–350
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
- $320–700
- Website
- Amtrak
Train from South Station to TF Green Airport
- Ave. Duration
- 1h 25m
- Frequency
- Every 4 hours
- Estimated price
- $9–16
- Website
- Massachusetts Bay Transportation Authority
- Website
- MBTA: World Cup 2026
- Adult
- $9–16
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 25m
- Frequency
- Every 2 hours
- Estimated price
- $35–75
- Website
- Greyhound
Bus from Boston to Boston Manchester Airport
- Ave. Duration
- 1h 5m
- Frequency
- 4 times a day
- Estimated price
- $7–15
- Website
- Greyhound
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Boston to Newark Penn Station
- Ave. Duration
- 4h 50m
- Frequency
- Every 4 hours
- Estimated price
- $40–70
- Schedules at
- Flixbus USA
Bus from Newark Penn Station to Chicago Bus Station
- Ave. Duration
- 16h 20m
- Frequency
- 4 times a day
- Estimated price
- $130–220
- Schedules at
- Flixbus USA
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More Questions & Answers
The quickest flight from Boston Logan Airport Airport to Chicago Midway International Airport Airport is the direct flight which takes 2h 30m.
Boston to Chicago Midway Airport (MDW) bus services, operated by Greyhound USA, arrive at Newark Penn Station.
Chicago Midway Airport (MDW) is 1h behind Boston. It is currently 3:37 PM in Boston and 2:37 PM in Chicago Midway Airport (MDW).
Boston to Chicago Midway Airport (MDW) train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Boston to Chicago Midway Airport (MDW) is 986 miles. It takes approximately 16h 50m to drive from Boston to Chicago Midway Airport (MDW).
Delta and Southwest Airlines offer flights from Boston Logan Airport Airport to Chicago Midway International Airport Airport.
There are 1149+ hotels available in Chicago Midway Airport (MDW).