Airlines with flights from Dallas to Chicago

There are two airlines with scheduled flights between DAL and MDW. Southwest is the only airline with non-stop flights from Dallas Love Fld to Midway International Airport and the flight time is 2 hours and 10 minutes.

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Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 2 hours and 10 minutes
  • Low-cost airline
  • Dallas and Chicago are both Southwest Airlines focus cities.
  • 52 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
DAL
Direct
MDW
 
Flight
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Aug 3
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Aug 9
WN105
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06:00
06:00
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WN130
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06:00
06:00
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06:00
WN1355
06:00
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WN4059
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06:05
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WN1313
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07:20
07:20
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WN1324
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08:15
08:15
10:40
10:40
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WN1356
08:30
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WN586
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09:40
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WN694
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09:50
09:50
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WN1357
10:05
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WN1328
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10:40
WN1032
12:05
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WN855
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12:10
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WN3613
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13:10
13:10
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WN1326
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14:25
14:25
13:35
13:35
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18:10
WN4201
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13:40
WN1358
14:05
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WN1327
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17:05
17:05
14:55
14:55
17:00
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WN36
16:50
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WN1225
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18:30
18:30
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WN370
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18:30
18:30
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WN1312
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19:45
WN107
19:50
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WN668
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21:10
21:10
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WN1359
22:50
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SHOW RETURN SCHEDULE
CHECK PRICES FOR DAL - MDW

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

Southwest Airlines

Via Saint Louis with Southwest Airlines

  • Total flight time: 3h 25m - 7h 40m.
  • Low-cost airline
  • Dallas and Chicago are both Southwest Airlines focus cities.
  • 126 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
DAL
 
Via STL
 
MDW
 
Flight
Mon
Aug 3
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Aug 4
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Aug 5
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Fri
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Aug 8
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Aug 9
WN1373
WN2814
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06:00
WN1373
WN3862
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07:40
07:40
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WN1400
WN3861
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08:00
08:00
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WN4699
WN2052
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09:10
09:10
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WN1411
WN3344
09:15
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WN1733
WN3862
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10:05
10:05
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WN1522
WN2052
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11:00
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WN865
WN2742
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11:20
WN1522
WN3864
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12:45
12:45
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WN1412
WN556
13:00
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WN1375
WN3865
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16:10
16:10
16:10
16:10
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WN1418
WN2032
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16:20
WN2921
WN3957
17:25
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WN4120
WN3865
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18:30
18:30
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SHOW RETURN SCHEDULE
CHECK PRICES FOR DAL - MDW

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

Southwest Airlines

Via Kansas City with Southwest Airlines

  • Total flight time: 3h 35m - 7h 25m.
  • Low-cost airline
  • Dallas and Chicago are both Southwest Airlines focus cities.
  • 122 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
DAL
 
Via MCI
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
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Aug 9
WN4631
WN1774
06:00
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WN4221
WN294
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06:10
WN1314
WN4829
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08:05
WN1343
WN2571
08:35
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WN346
WN4829
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09:20
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WN768
WN2522
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11:15
11:15
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WN1315
WN2525
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11:55
11:55
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12:25
WN4327
WN2572
12:00
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WN1315
WN2522
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12:20
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WN1328
WN2525
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12:55
12:55
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WN3068
WN345
15:55
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WN232
WN2604
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17:20
WN1968
WN4630
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17:55
17:55
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SHOW RETURN SCHEDULE
CHECK PRICES FOR DAL - MDW

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

Southwest Airlines

Via Tulsa with Southwest Airlines

  • Total flight time: 3h 40m - 5h 45m.
  • Low-cost airline
  • Dallas and Chicago are both Southwest Airlines focus cities.
  • 6 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
DAL
 
Via TUL
 
MDW
 
Flight
Mon
Aug 3
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Aug 4
Wed
Aug 5
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Aug 6
Fri
Aug 7
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Aug 8
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Aug 9
WN3723
WN4614
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09:20
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WN4055
WN931
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11:20
SHOW RETURN SCHEDULE
CHECK PRICES FOR DAL - MDW

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

Southwest Airlines

Via Milwaukee with Southwest Airlines

  • Total flight time: 3h 50m - 6h 05m.
  • Low-cost airline
  • Dallas and Chicago are both Southwest Airlines focus cities.
  • 13 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
DAL
 
Via MKE
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
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Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN887
WN450
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12:30
WN925
WN2953
13:35
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SHOW RETURN SCHEDULE
CHECK PRICES FOR DAL - MDW

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

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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.
Flight data on this page was last updated on 2026-07-13
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