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.

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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).
  • 31 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
MDW
Direct
BOS
 
Flight
Mon
Dec 2
Tue
Dec 3
Wed
Dec 4
Thu
Dec 5
Fri
Dec 6
Sat
Dec 7
Sun
Dec 8
WN2229
06:25
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20:30
WN2666
----
08:30
08:30
08:30
08:30
08:05
08:00
WN5421
09:45
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WN4815
----
----
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----
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13:15
14:20
WN3701
14:55
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WN1933
----
18:25
18:25
18:25
18:25
16:45
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WN1350
20:25
----
----
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - BOS

The timetable & schedule information was updated at 2024-11-19

Via Baltimore with Southwest Airlines

  • Total flight time: 3h 55m - 8h 25m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 65 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
MDW
 
Via BWI
 
BOS
 
Flight
Mon
Dec 2
Tue
Dec 3
Wed
Dec 4
Thu
Dec 5
Fri
Dec 6
Sat
Dec 7
Sun
Dec 8
WN281
WN1304
05:25
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----
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----
WN2861
WN2456
05:30
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----
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----
----
----
WN6341
WN2456
06:25
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----
----
----
----
----
WN2665
WN1828
13:20
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----
----
----
----
06:25
WN281
WN2844
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----
----
----
----
06:40
----
WN794
WN2357
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07:15
07:15
07:15
07:15
----
----
WN1382
WN2986
----
07:20
07:20
07:20
07:20
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----
WN1796
WN954
08:05
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----
----
----
----
----
WN4325
WN2986
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----
----
----
----
----
08:15
WN1384
WN2986
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----
----
----
----
----
08:15
WN4633
WN954
08:15
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----
----
----
----
----
WN1285
WN2986
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----
----
----
----
09:00
----
WN3219
WN1828
----
09:00
09:00
09:00
09:00
----
----
WN4325
WN1962
----
----
----
----
----
09:00
----
WN3381
WN2986
----
----
----
----
----
09:15
----
WN1035
WN4239
----
10:05
10:05
10:05
10:05
----
----
WN1079
WN2986
10:15
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----
----
----
----
----
WN6312
WN2986
11:05
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----
----
----
----
----
WN3223
WN1545
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----
----
----
----
----
11:30
WN3504
WN1545
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----
----
----
----
----
11:40
WN4736
WN3239
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----
----
----
----
----
11:45
WN1997
WN1545
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----
----
----
----
----
12:35
WN1997
WN3773
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----
----
----
----
----
12:35
WN2993
WN400
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----
----
----
----
12:40
----
WN3212
WN3126
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----
----
----
----
12:45
----
WN1488
WN3126
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----
----
----
----
----
13:05
WN259
WN3773
----
13:10
13:10
13:10
13:10
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----
WN2226
WN4913
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----
----
----
----
13:15
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WN6413
WN4913
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----
----
----
----
----
14:50
WN1351
WN4913
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----
----
----
----
----
15:00
WN3094
WN4913
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----
----
----
----
----
16:00
WN2389
WN3306
16:30
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----
----
----
----
----
WN1833
WN3306
16:30
----
----
----
----
----
----
WN6433
WN2456
----
----
----
----
----
----
17:00
WN1964
WN3306
17:10
----
----
----
----
----
----
WN1488
WN4422
19:00
----
----
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - BOS

The timetable & schedule information was updated at 2024-11-19

Via Nashville with Southwest Airlines

  • Total flight time: 4h 30m - 8h 15m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 23 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
MDW
 
Via BNA
 
BOS
 
Flight
Mon
Dec 2
Tue
Dec 3
Wed
Dec 4
Thu
Dec 5
Fri
Dec 6
Sat
Dec 7
Sun
Dec 8
WN281
WN1304
05:25
----
----
----
----
----
----
WN2861
WN2456
05:30
----
----
----
----
----
----
WN6341
WN2456
06:25
----
----
----
----
----
----
WN2665
WN1828
13:20
----
----
----
----
----
06:25
WN281
WN2844
----
----
----
----
----
06:40
----
WN794
WN2357
----
07:15
07:15
07:15
07:15
----
----
WN1382
WN2986
----
07:20
07:20
07:20
07:20
----
----
WN1796
WN954
08:05
----
----
----
----
----
----
WN4325
WN2986
----
----
----
----
----
----
08:15
WN1384
WN2986
----
----
----
----
----
----
08:15
WN4633
WN954
08:15
----
----
----
----
----
----
WN1285
WN2986
----
----
----
----
----
09:00
----
WN3219
WN1828
----
09:00
09:00
09:00
09:00
----
----
WN4325
WN1962
----
----
----
----
----
09:00
----
WN3381
WN2986
----
----
----
----
----
09:15
----
WN1035
WN4239
----
10:05
10:05
10:05
10:05
----
----
WN1079
WN2986
10:15
----
----
----
----
----
----
WN6312
WN2986
11:05
----
----
----
----
----
----
WN3223
WN1545
----
----
----
----
----
----
11:30
WN3504
WN1545
----
----
----
----
----
----
11:40
WN4736
WN3239
----
----
----
----
----
----
11:45
WN1997
WN1545
----
----
----
----
----
----
12:35
WN1997
WN3773
----
----
----
----
----
----
12:35
WN2993
WN400
----
----
----
----
----
12:40
----
WN3212
WN3126
----
----
----
----
----
12:45
----
WN1488
WN3126
----
----
----
----
----
----
13:05
WN259
WN3773
----
13:10
13:10
13:10
13:10
----
----
WN2226
WN4913
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----
----
----
----
13:15
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WN6413
WN4913
----
----
----
----
----
----
14:50
WN1351
WN4913
----
----
----
----
----
----
15:00
WN3094
WN4913
----
----
----
----
----
----
16:00
WN2389
WN3306
16:30
----
----
----
----
----
----
WN1833
WN3306
16:30
----
----
----
----
----
----
WN6433
WN2456
----
----
----
----
----
----
17:00
WN1964
WN3306
17:10
----
----
----
----
----
----
WN1488
WN4422
19:00
----
----
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - BOS

The timetable & schedule information was updated at 2024-11-19

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).
  • 18 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
MDW
 
Via STL
 
BOS
 
Flight
Mon
Dec 2
Tue
Dec 3
Wed
Dec 4
Thu
Dec 5
Fri
Dec 6
Sat
Dec 7
Sun
Dec 8
WN281
WN1304
05:25
----
----
----
----
----
----
WN2861
WN2456
05:30
----
----
----
----
----
----
WN6341
WN2456
06:25
----
----
----
----
----
----
WN2665
WN1828
13:20
----
----
----
----
----
06:25
WN281
WN2844
----
----
----
----
----
06:40
----
WN794
WN2357
----
07:15
07:15
07:15
07:15
----
----
WN1382
WN2986
----
07:20
07:20
07:20
07:20
----
----
WN1796
WN954
08:05
----
----
----
----
----
----
WN4325
WN2986
----
----
----
----
----
----
08:15
WN1384
WN2986
----
----
----
----
----
----
08:15
WN4633
WN954
08:15
----
----
----
----
----
----
WN1285
WN2986
----
----
----
----
----
09:00
----
WN3219
WN1828
----
09:00
09:00
09:00
09:00
----
----
WN4325
WN1962
----
----
----
----
----
09:00
----
WN3381
WN2986
----
----
----
----
----
09:15
----
WN1035
WN4239
----
10:05
10:05
10:05
10:05
----
----
WN1079
WN2986
10:15
----
----
----
----
----
----
WN6312
WN2986
11:05
----
----
----
----
----
----
WN3223
WN1545
----
----
----
----
----
----
11:30
WN3504
WN1545
----
----
----
----
----
----
11:40
WN4736
WN3239
----
----
----
----
----
----
11:45
WN1997
WN1545
----
----
----
----
----
----
12:35
WN1997
WN3773
----
----
----
----
----
----
12:35
WN2993
WN400
----
----
----
----
----
12:40
----
WN3212
WN3126
----
----
----
----
----
12:45
----
WN1488
WN3126
----
----
----
----
----
----
13:05
WN259
WN3773
----
13:10
13:10
13:10
13:10
----
----
WN2226
WN4913
----
----
----
----
----
13:15
----
WN6413
WN4913
----
----
----
----
----
----
14:50
WN1351
WN4913
----
----
----
----
----
----
15:00
WN3094
WN4913
----
----
----
----
----
----
16:00
WN2389
WN3306
16:30
----
----
----
----
----
----
WN1833
WN3306
16:30
----
----
----
----
----
----
WN6433
WN2456
----
----
----
----
----
----
17:00
WN1964
WN3306
17:10
----
----
----
----
----
----
WN1488
WN4422
19:00
----
----
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - BOS

The timetable & schedule information was updated at 2024-11-19

Via Detroit with Delta Air Lines

  • Total flight time: 3h 38m - 5h 55m.
  • Sky Team Alliance
  • Boston is a Delta Air Lines hub.
  • 13 flights per week
MDW
 
Via DTW
 
BOS
 
Flight
Mon
Dec 2
Tue
Dec 3
Wed
Dec 4
Thu
Dec 5
Fri
Dec 6
Sat
Dec 7
Sun
Dec 8
DL3648
DL1171
09:31
09:31
09:31
09:31
09:30
----
09:30
DL3778
DL2558
09:30
09:30
09:30
09:30
09:38
----
09:38
DL3867
DL1707
13:30
13:30
13:30
13:30
13:30
----
13:30
DL3869
DL1187
17:42
17:42
17:42
17:42
17:50
17:50
17:50
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - BOS

The timetable & schedule information was updated at 2024-11-19

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