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 15 minutes.

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Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 2 hours and 15 minutes
  • Low-cost airline
  • Dallas and Chicago are both Southwest Airlines focus cities.
  • 58 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
DAL
Direct
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN1355
06:00
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06:00
06:00
06:00
06:10
WN1307
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07:15
07:15
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WN1356
08:30
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08:30
08:30
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WN2744
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09:15
WN1517
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09:45
09:45
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WN8
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10:00
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WN1357
10:05
12:25
12:25
10:05
10:05
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WN1358
14:05
15:00
15:00
14:05
14:05
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13:10
WN1006
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----
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14:35
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WN1359
22:50
21:55
21:55
22:50
22:50
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15:50
WN36
16:50
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16:50
16:50
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WN987
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18:30
18:30
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WN107
19:50
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19:50
19:50
18:45
18:55
WN2103
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19:50
19:50
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WN1189
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20:55
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WN1151
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----
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21:25
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 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
DAL
 
Via STL
 
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN2445
WN2665
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07:15
07:15
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WN1411
WN3344
09:15
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09:15
09:15
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WN1411
WN2832
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11:00
WN1412
WN556
13:00
13:25
13:25
13:00
13:00
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WN1346
WN556
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13:00
WN426
WN3957
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----
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14:15
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WN2921
WN3957
17:25
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17:25
17:25
18:15
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WN3456
WN3957
----
----
----
----
----
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17:25
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 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
DAL
 
Via MCI
 
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN4631
WN3980
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06:00
06:00
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WN4631
WN1774
06:00
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06:00
06:00
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06:20
WN2856
WN1037
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07:40
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WN1343
WN2571
08:35
08:45
08:45
08:35
08:35
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WN4257
WN2571
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10:20
WN4327
WN2572
12:00
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12:00
12:00
11:00
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WN2953
WN3850
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12:00
12:00
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WN936
WN2787
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----
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----
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13:40
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WN1346
WN345
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14:40
14:40
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WN3068
WN2572
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----
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15:25
WN3068
WN345
15:55
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15:55
15:55
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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 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
DAL
 
Via TUL
 
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
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 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
DAL
 
Via MKE
 
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN925
WN2953
13:35
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----
13:35
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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Flight data on this page was last updated on 2026-06-02
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