Airlines with flights from Chicago to Dallas

There are two airlines with scheduled flights between MDW and DAL. Southwest is the only airline with non-stop flights from Midway International Airport to Dallas Love Fld and the flight time is 2 hours and 25 minutes.

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Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 2 hours and 25 minutes
  • Low-cost airline
  • Chicago and Dallas are both Southwest Airlines focus cities.
  • 60 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
Direct
DAL
 
Flight
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Jun 15
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Jun 21
WN1559
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05:00
WN1377
05:00
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05:00
05:00
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WN2661
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05:05
05:05
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WN1370
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06:30
06:30
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WN1321
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06:30
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WN3796
06:40
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06:40
06:40
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WN2253
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07:25
WN163
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08:50
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WN3790
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09:55
WN1487
10:00
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10:00
10:00
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WN1331
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11:30
11:30
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WN2757
12:20
13:55
13:55
12:20
12:20
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WN488
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13:40
WN938
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14:55
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WN2758
16:20
15:20
15:20
16:20
16:20
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WN59
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18:05
18:05
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WN2961
18:15
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18:15
18:15
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19:30
WN1255
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19:00
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WN1005
20:40
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20:40
20:40
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WN3024
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20:55
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WN2663
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20:55
20:55
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WN998
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21:05
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - DAL

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

Southwest Airlines

Via Saint Louis with Southwest Airlines

  • Total flight time: 3h 30m - 6h 05m.
  • Low-cost airline
  • Chicago and Dallas are both Southwest Airlines focus cities.
  • 93 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
 
Via STL
 
DAL
 
Flight
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Jun 15
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Jun 16
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Jun 19
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Jun 20
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Jun 21
WN2900
WN1056
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06:30
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WN2901
WN3749
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10:00
10:00
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WN2901
WN339
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10:05
WN2901
WN1322
11:00
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11:00
11:00
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WN2902
WN1792
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11:25
11:25
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WN2902
WN3597
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13:10
WN2903
WN3597
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14:35
14:35
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WN2903
WN1417
14:45
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14:45
14:45
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WN2904
WN3904
18:00
17:10
17:10
18:00
18:00
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WN1646
WN962
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18:30
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - DAL

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

Southwest Airlines

Via Kansas City with Southwest Airlines

  • Total flight time: 3h 35m - 7h 35m.
  • Low-cost airline
  • Chicago and Dallas are both Southwest Airlines focus cities.
  • 129 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
 
Via MCI
 
DAL
 
Flight
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Jun 15
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Jun 16
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Jun 17
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Jun 18
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Jun 19
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Jun 20
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Jun 21
WN2635
WN1422
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06:30
WN489
WN4759
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07:50
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WN2933
WN25
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07:50
07:50
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WN2529
WN4759
10:20
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10:20
10:20
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WN709
WN1765
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10:25
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WN4407
WN1323
14:10
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14:10
14:10
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11:50
WN3572
WN845
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12:05
12:05
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WN103
WN2540
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14:35
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WN427
WN1583
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14:45
14:45
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WN4407
WN2540
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15:25
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WN2812
WN2540
16:05
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16:05
16:05
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WN457
WN4455
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18:30
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - DAL

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

Southwest Airlines

Via Nashville with Southwest Airlines

  • Total flight time: 4h 00m - 8h 10m.
  • Low-cost airline
  • Chicago and Dallas are both Southwest Airlines focus cities.
  • 143 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
 
Via BNA
 
DAL
 
Flight
Mon
Jun 15
Tue
Jun 16
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Jun 17
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Jun 18
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Jun 19
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Jun 20
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Jun 21
WN3855
WN487
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06:10
WN1053
WN4466
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06:40
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WN2959
WN487
07:15
08:40
08:40
07:15
07:15
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WN1708
WN487
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07:45
07:45
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WN1775
WN5076
07:55
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07:55
07:55
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WN1337
WN5078
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07:55
WN1775
WN488
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08:00
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WN1775
WN1136
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08:30
WN1257
WN487
09:00
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09:00
09:00
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WN2733
WN488
11:20
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11:20
11:20
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WN533
WN1136
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11:50
WN2733
WN1758
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11:50
11:50
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WN3869
WN489
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15:10
15:10
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WN1257
WN490
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15:30
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WN3869
WN3230
17:05
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17:05
17:05
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WN1073
WN3230
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17:20
17:20
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18:35
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - DAL

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

Southwest Airlines

Via Memphis with Southwest Airlines

  • Total flight time: 4h 00m - 6h 00m.
  • Low-cost airline
  • Chicago and Dallas are both Southwest Airlines focus cities.
  • 12 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
 
Via MEM
 
DAL
 
Flight
Mon
Jun 15
Tue
Jun 16
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Jun 17
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Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN2824
WN4127
10:05
10:15
10:15
10:05
10:05
13:00
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - DAL

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

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Flight data on this page was last updated on 2026-06-02
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