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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Choose airline

Schedules

Southwest Airlines

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).
  • 34 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
BOS
Direct
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN3239
05:25
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WN744
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07:30
07:30
07:30
07:30
07:05
07:30
WN745
07:30
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WN175
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08:40
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WN1585
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09:25
WN1645
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10:05
10:05
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WN2421
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12:40
12:40
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WN4298
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13:00
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WN746
13:10
15:20
15:20
18:40
18:40
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WN4657
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13:55
WN3480
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15:25
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WN672
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19:20
19:15
15:55
15:55
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WN4106
16:45
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WN3738
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17:35
WN3911
18:45
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WN3183
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20:20
20:20
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WN2662
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21:05
SHOW RETURN SCHEDULE
CHECK PRICES FOR BOS - MDW

The timetable & schedule information was updated at 2026-04-21

Delta Air Lines

Via Detroit with Delta Air Lines

  • Total flight time: 4h 03m - 6h 23m.
  • Sky Team Alliance
  • Boston is a Delta Air Lines hub.
  • 69 flights per week
BOS
 
Via DTW
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
DL1019
DL4684
05:40
05:40
05:40
05:40
05:40
05:40
05:40
DL1748
DL4688
09:15
09:15
09:15
09:15
09:15
09:15
09:15
DL2222
DL4677
13:10
13:10
13:10
13:10
13:10
13:10
13:10
SHOW RETURN SCHEDULE
CHECK PRICES FOR BOS - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Baltimore with Southwest Airlines

  • Total flight time: 4h 15m - 8h 55m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 128 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
BOS
 
Via BWI
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN1642
WN4094
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05:25
05:25
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05:50
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WN727
WN4217
05:45
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WN857
WN992
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05:50
05:50
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WN1642
WN1683
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05:55
WN280
WN1070
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07:40
07:40
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WN3985
WN915
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----
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08:10
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WN4333
WN1359
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08:15
08:15
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WN732
WN435
09:10
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WN2409
WN1195
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09:40
09:40
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WN2098
WN450
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10:45
WN2098
WN992
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10:50
10:50
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WN1377
WN992
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12:10
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WN733
WN997
13:20
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WN858
WN425
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13:20
13:20
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WN2098
WN329
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14:15
14:15
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WN858
WN1195
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14:40
WN735
WN1195
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14:45
14:45
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WN2439
WN4094
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15:35
15:35
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WN1053
WN998
15:55
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WN735
WN4821
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16:35
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WN3823
WN4002
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16:55
16:55
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WN1898
WN999
17:20
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SHOW RETURN SCHEDULE
CHECK PRICES FOR BOS - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Saint Louis with Southwest Airlines

  • Total flight time: 4h 30m - 6h 50m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 49 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
BOS
 
Via STL
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN999
WN3862
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----
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05:30
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WN4587
WN2814
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05:30
WN752
WN2570
05:35
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WN960
WN2052
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10:45
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WN4917
WN556
12:55
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WN999
WN3865
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17:45
17:45
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WN2076
WN3865
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17:50
17:50
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WN754
WN3957
18:50
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----
----
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SHOW RETURN SCHEDULE
CHECK PRICES FOR BOS - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Nashville with Southwest Airlines

  • Total flight time: 5h 10m - 9h 05m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 61 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
BOS
 
Via BNA
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN1202
WN573
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05:25
05:25
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WN725
WN573
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08:30
08:30
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WN1530
WN573
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09:55
WN446
WN575
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12:10
WN1530
WN576
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14:10
14:10
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WN1674
WN576
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15:00
15:00
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WN1030
WN577
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16:45
WN1257
WN577
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17:50
17:50
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WN2338
WN578
20:00
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----
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----
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----
SHOW RETURN SCHEDULE
CHECK PRICES FOR BOS - MDW

The timetable & schedule information was updated at 2026-04-21

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Flight data on this page was last updated on 2026-07-21
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