Airlines with flights from Boston to Chicago

There are two airlines with scheduled flights between BOS and MDW. Southwest is the only airline with non-stop flights from Logan Airport to Midway International Airport and the flight time is 2 hours and 45 minutes.

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Schedules

Non-stop with Southwest Airlines

  • Total flight time: 2 hours and 45 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 32 flights per week
BOS
Direct
MDW
 
Flight
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SHOW RETURN SCHEDULE
CHECK PRICES FOR BOS - MDW

The timetable & schedule information was updated at 2024-12-13

Via Baltimore with Southwest Airlines

  • Total flight time: 4h 15m - 9h 00m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 32 flights per week
BOS
 
Via BWI
 
MDW
 
Flight
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SHOW RETURN SCHEDULE
CHECK PRICES FOR BOS - MDW

The timetable & schedule information was updated at 2024-12-13

Via Detroit with Delta Air Lines

  • Total flight time: 4h 17m - 5h 15m.
  • Sky Team Alliance
  • Boston is a Delta Air Lines hub.
  • 20 flights per week
BOS
 
Via DTW
 
MDW
 
Flight
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SHOW RETURN SCHEDULE
CHECK PRICES FOR BOS - MDW

The timetable & schedule information was updated at 2024-12-13

Via Minneapolis with Delta Air Lines

  • Total flight time: 5h 52m - 7h 56m.
  • Sky Team Alliance
  • Boston is a Delta Air Lines hub.
  • 20 flights per week
BOS
 
Via MSP
 
MDW
 
Flight
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Jan 7
SHOW RETURN SCHEDULE
CHECK PRICES FOR BOS - MDW

The timetable & schedule information was updated at 2024-12-13

Via Nashville with Southwest Airlines

  • Total flight time: 5h 05m - 9h 35m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 20 flights per week
BOS
 
Via BNA
 
MDW
 
Flight
Mon
Jan 1
Tue
Jan 2
Wed
Jan 3
Thu
Jan 4
Fri
Jan 5
Sat
Jan 6
Sun
Jan 7
SHOW RETURN SCHEDULE
CHECK PRICES FOR BOS - MDW

The timetable & schedule information was updated at 2024-12-13

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