Airlines with flights from Chicago to Boston

There are two airlines with scheduled flights between MDW and BOS. Southwest is the only airline with non-stop flights from Midway International Airport to Logan Airport and the flight time is 2 hours and 15 minutes.

Change direction

Choose airline

Schedules

Non-stop with Southwest Airlines

  • Total flight time: 2 hours and 15 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 21 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
Direct
BOS
 
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
WN1841
----
----
----
----
----
06:25
----
WN2666
08:05
08:40
10:05
08:40
08:05
----
08:05
WN4815
15:50
----
----
----
15:50
----
15:50
WN1933
----
19:00
18:25
19:00
----
18:55
----
WN332
20:20
----
----
----
20:20
----
20:20
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - BOS

The timetable & schedule information was updated at 2025-01-15

Via Baltimore with Southwest Airlines

  • Total flight time: 3h 55m - 8h 25m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 33 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
 
Via BWI
 
BOS
 
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
WN568
WN2357
05:25
----
----
----
05:25
----
05:25
WN2665
WN1828
----
05:55
06:25
05:55
----
----
----
WN1502
WN2357
----
06:00
----
06:00
----
----
----
WN952
WN4109
----
----
----
----
----
06:00
----
WN281
WN2844
----
----
----
----
----
06:10
----
WN4684
WN2986
----
07:35
----
07:35
----
----
----
WN1324
WN1686
----
----
----
----
----
08:00
----
WN978
WN3773
----
10:00
----
10:00
----
----
----
WN1385
WN4239
10:05
----
----
----
10:05
----
10:05
WN1285
WN3773
----
----
----
----
----
10:05
----
WN1285
WN2986
----
----
----
----
----
10:05
----
WN2886
WN4239
----
----
10:05
----
----
----
----
WN1035
WN4239
----
----
10:30
----
----
----
----
WN1277
WN3126
----
----
11:05
----
----
----
----
WN3254
WN2895
----
13:25
----
13:25
----
----
----
WN1035
WN2895
----
14:20
----
14:20
----
----
----
WN1833
WN4913
----
14:50
14:25
14:50
----
----
----
WN3334
WN3291
14:30
----
----
----
14:30
----
14:30
WN3710
WN3291
14:40
----
----
----
14:40
----
14:40
WN3899
WN3291
14:45
----
----
----
14:45
----
14:45
WN1351
WN400
----
----
----
----
----
15:10
----
WN651
WN2456
----
----
15:15
----
----
----
----
WN972
WN2456
----
16:20
----
16:20
----
----
----
WN1689
WN4913
16:25
----
----
----
16:25
----
16:25
WN2962
WN3126
----
----
----
----
----
16:50
----
WN3786
WN4913
----
----
17:05
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - BOS

The timetable & schedule information was updated at 2025-01-15

Via Detroit with Delta Air Lines

  • Total flight time: 3h 44m - 5h 59m.
  • Sky Team Alliance
  • Boston is a Delta Air Lines hub.
  • 20 flights per week
MDW
 
Via DTW
 
BOS
 
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
DL3858
DL1171
09:33
09:33
09:33
09:33
09:33
09:33
09:33
DL3778
DL2591
----
----
----
----
----
11:25
----
DL3867
DL1707
14:08
14:08
14:08
14:08
14:08
----
14:08
DL3869
DL5858
----
----
----
----
----
17:05
----
DL3843
DL1187
18:28
18:28
18:28
18:28
18:28
----
18:28
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - BOS

The timetable & schedule information was updated at 2025-01-15

Via Nashville with Southwest Airlines

  • Total flight time: 4h 35m - 8h 40m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 14 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
 
Via BNA
 
BOS
 
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
WN568
WN2357
05:25
----
----
----
05:25
----
05:25
WN2665
WN1828
----
05:55
06:25
05:55
----
----
----
WN1502
WN2357
----
06:00
----
06:00
----
----
----
WN952
WN4109
----
----
----
----
----
06:00
----
WN281
WN2844
----
----
----
----
----
06:10
----
WN4684
WN2986
----
07:35
----
07:35
----
----
----
WN1324
WN1686
----
----
----
----
----
08:00
----
WN978
WN3773
----
10:00
----
10:00
----
----
----
WN1385
WN4239
10:05
----
----
----
10:05
----
10:05
WN1285
WN3773
----
----
----
----
----
10:05
----
WN1285
WN2986
----
----
----
----
----
10:05
----
WN2886
WN4239
----
----
10:05
----
----
----
----
WN1035
WN4239
----
----
10:30
----
----
----
----
WN1277
WN3126
----
----
11:05
----
----
----
----
WN3254
WN2895
----
13:25
----
13:25
----
----
----
WN1035
WN2895
----
14:20
----
14:20
----
----
----
WN1833
WN4913
----
14:50
14:25
14:50
----
----
----
WN3334
WN3291
14:30
----
----
----
14:30
----
14:30
WN3710
WN3291
14:40
----
----
----
14:40
----
14:40
WN3899
WN3291
14:45
----
----
----
14:45
----
14:45
WN1351
WN400
----
----
----
----
----
15:10
----
WN651
WN2456
----
----
15:15
----
----
----
----
WN972
WN2456
----
16:20
----
16:20
----
----
----
WN1689
WN4913
16:25
----
----
----
16:25
----
16:25
WN2962
WN3126
----
----
----
----
----
16:50
----
WN3786
WN4913
----
----
17:05
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - BOS

The timetable & schedule information was updated at 2025-01-15

Via Saint Louis with Southwest Airlines

  • Total flight time: 4h 20m - 6h 50m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 8 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
 
Via STL
 
BOS
 
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
WN568
WN2357
05:25
----
----
----
05:25
----
05:25
WN2665
WN1828
----
05:55
06:25
05:55
----
----
----
WN1502
WN2357
----
06:00
----
06:00
----
----
----
WN952
WN4109
----
----
----
----
----
06:00
----
WN281
WN2844
----
----
----
----
----
06:10
----
WN4684
WN2986
----
07:35
----
07:35
----
----
----
WN1324
WN1686
----
----
----
----
----
08:00
----
WN978
WN3773
----
10:00
----
10:00
----
----
----
WN1385
WN4239
10:05
----
----
----
10:05
----
10:05
WN1285
WN3773
----
----
----
----
----
10:05
----
WN1285
WN2986
----
----
----
----
----
10:05
----
WN2886
WN4239
----
----
10:05
----
----
----
----
WN1035
WN4239
----
----
10:30
----
----
----
----
WN1277
WN3126
----
----
11:05
----
----
----
----
WN3254
WN2895
----
13:25
----
13:25
----
----
----
WN1035
WN2895
----
14:20
----
14:20
----
----
----
WN1833
WN4913
----
14:50
14:25
14:50
----
----
----
WN3334
WN3291
14:30
----
----
----
14:30
----
14:30
WN3710
WN3291
14:40
----
----
----
14:40
----
14:40
WN3899
WN3291
14:45
----
----
----
14:45
----
14:45
WN1351
WN400
----
----
----
----
----
15:10
----
WN651
WN2456
----
----
15:15
----
----
----
----
WN972
WN2456
----
16:20
----
16:20
----
----
----
WN1689
WN4913
16:25
----
----
----
16:25
----
16:25
WN2962
WN3126
----
----
----
----
----
16:50
----
WN3786
WN4913
----
----
17:05
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - BOS

The timetable & schedule information was updated at 2025-01-15

Change direction

Staying up-to-date with the airlines

At Airlineinformation.com you can learn all about the airlines operating around the world together with their destinations and where they operate. You will get a transparent overview of airlines with scheduled flights between any two destinations with non-stop or 1-stop flights regardless of price or availability.
© 2025 Westcoast Digital