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.
  • 54 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
Direct
DAL
 
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
WN1377
05:00
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WN1005
20:40
19:45
19:45
05:30
05:30
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WN2706
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06:00
06:00
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WN4025
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06:10
WN3796
06:40
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WN199
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08:20
08:20
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06:45
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WN1060
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07:15
WN2707
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07:25
07:25
10:15
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WN1487
10:00
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WN1152
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10:30
10:30
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WN35
11:00
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WN1148
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11:10
11:10
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WN2757
12:20
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WN2708
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12:30
12:30
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12:30
WN966
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13:55
13:55
19:00
19:00
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WN1271
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14:15
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WN1356
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15:10
15:10
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WN2709
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15:50
WN2758
16:20
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WN2711
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17:15
17:15
16:30
16:30
18:05
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WN2132
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17:55
17:55
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WN2961
18:25
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WN694
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18:50
WN4222
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20:15
WN147
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20:40
20:40
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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 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via STL
 
DAL
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2837
WN471
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06:35
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WN370
WN4585
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09:55
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WN2838
WN4823
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10:10
10:10
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WN2901
WN1322
11:00
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WN2838
WN1535
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11:10
WN591
WN4586
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13:55
13:55
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WN2903
WN1417
14:45
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WN2839
WN4585
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15:10
15:10
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WN126
WN3821
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16:40
16:40
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WN4254
WN3821
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17:50
17:50
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17:50
WN2904
WN3904
18:00
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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 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via MCI
 
DAL
 
Flight
Mon
Aug 3
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Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2807
WN1956
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06:20
06:20
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WN4239
WN4031
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07:15
07:15
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WN2755
WN240
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07:45
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WN2755
WN1281
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08:00
WN2755
WN3760
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08:55
08:55
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WN2529
WN4759
10:20
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WN615
WN4386
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10:40
10:40
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WN2754
WN193
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11:30
WN2754
WN2747
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11:55
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WN1180
WN4193
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12:00
12:00
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WN4407
WN1323
14:10
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WN875
WN4194
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14:45
14:45
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WN2874
WN4194
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14:50
14:50
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WN2812
WN2540
16:05
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WN2754
WN4194
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16:15
16:15
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WN163
WN1394
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17:00
17:00
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WN984
WN2490
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17:35
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 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via BNA
 
DAL
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN508
WN2123
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05:55
05:55
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WN2959
WN487
07:15
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WN1409
WN4814
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07:40
07:40
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WN1799
WN485
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07:55
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WN1775
WN5076
07:55
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WN120
WN1417
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08:00
08:00
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WN2676
WN485
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08:05
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WN1072
WN485
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08:15
08:15
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WN485
WN486
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08:50
08:50
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WN442
WN485
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08:50
WN1257
WN487
09:00
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WN2676
WN4814
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09:05
09:05
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WN2733
WN488
11:20
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WN1585
WN486
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11:40
WN240
WN486
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12:35
12:35
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WN1704
WN3065
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13:00
13:00
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WN512
WN3065
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13:15
WN1035
WN3065
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13:55
WN2677
WN3065
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14:40
14:40
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14:25
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WN2676
WN3065
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15:20
15:20
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WN3869
WN3230
17:05
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WN4859
WN488
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17:20
17:20
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WN2677
WN4814
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17:30
17:30
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WN1794
WN488
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18:00
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 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via MEM
 
DAL
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2824
WN4127
10:05
----
----
----
----
----
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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 2026-07-13
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