Airlines with flights from Dallas to Chicago

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

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 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 (winglets) Passenger/BBJ1
DAL
Direct
MDW
 
Flight
Mon
Jan 13
Tue
Jan 14
Wed
Jan 15
Thu
Jan 16
Fri
Jan 17
Sat
Jan 18
Sun
Jan 19
WN573
06:55
06:55
06:55
----
----
----
06:55
WN1079
----
----
----
06:55
06:55
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----
WN1548
----
----
----
----
----
08:25
----
WN1365
11:25
11:25
11:25
----
----
----
11:25
WN2564
14:45
14:45
14:45
11:25
11:25
14:00
14:45
WN2329
17:45
17:45
17:45
17:15
17:15
----
17:45
WN298
----
----
----
19:00
19:00
----
----
WN381
19:55
19:55
19:55
21:15
21:15
----
19:55
SHOW RETURN SCHEDULE
CHECK PRICES FOR DAL - MDW

The timetable & schedule information was updated at 2024-12-13

Via Houston with Southwest Airlines

  • Total flight time: 4h 05m - 9h 35m.
  • Low-cost airline
  • Dallas and Chicago are both Southwest Airlines focus cities.
  • 51 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 (winglets) Passenger/BBJ1
DAL
 
Via HOU
 
MDW
 
Flight
Mon
Jan 13
Tue
Jan 14
Wed
Jan 15
Thu
Jan 16
Fri
Jan 17
Sat
Jan 18
Sun
Jan 19
WN201
WN2332
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06:00
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WN201
WN4499
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----
06:00
----
WN1859
WN2364
06:25
06:25
06:25
06:00
06:00
08:45
06:25
WN2819
WN3300
----
----
----
06:35
06:35
----
----
WN2007
WN198
----
----
----
06:45
06:45
----
----
WN2819
WN1119
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----
----
----
----
07:00
----
WN2007
WN736
07:10
07:10
07:10
----
----
----
----
WN561
WN162
----
----
----
----
----
07:15
----
WN3
WN2630
07:30
07:30
07:30
----
----
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----
WN561
WN1925
07:35
07:35
07:35
----
----
----
07:35
WN1077
WN1155
----
----
----
----
----
07:40
----
WN701
WN2847
----
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----
07:50
07:50
----
----
WN1623
WN1471
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----
----
07:55
07:55
----
----
WN1623
WN1791
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----
----
07:55
07:55
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----
WN1623
WN4877
08:15
08:15
08:15
----
----
----
08:15
WN7
WN2630
08:30
08:30
08:30
08:30
08:30
----
08:30
WN2016
WN198
----
----
----
08:30
08:30
----
----
WN9
WN2630
----
----
----
----
----
08:35
----
WN714
WN262
08:45
08:45
08:45
----
----
----
08:45
WN2016
WN3293
----
----
----
----
----
09:10
----
WN775
WN1471
----
----
----
09:35
09:35
----
----
WN1195
WN2434
----
----
----
----
----
09:45
----
WN15
WN2630
----
----
----
10:00
10:00
----
----
WN3118
WN1119
----
----
----
----
----
10:05
----
WN19
WN481
----
----
----
----
----
10:10
----
WN356
WN3109
10:30
10:30
10:30
----
----
----
10:30
WN1445
WN2913
10:40
10:40
10:40
----
----
----
10:40
WN652
WN4877
----
----
----
----
----
10:45
----
WN652
WN3079
----
----
----
----
----
10:45
----
WN2569
WN3079
10:45
10:45
10:45
----
----
----
10:45
WN652
WN3705
----
----
----
----
----
10:45
----
WN503
WN2434
----
----
----
11:00
11:00
----
----
WN2852
WN554
11:00
11:00
11:00
----
----
----
11:00
WN1754
WN4071
11:25
11:25
11:25
----
----
----
11:25
WN1754
WN3434
11:25
11:25
11:25
----
----
----
11:25
WN19
WN1260
11:30
11:30
11:30
----
----
----
11:30
WN19
WN1111
----
----
----
11:30
11:30
----
----
WN17
WN481
----
----
----
----
----
11:30
----
WN1445
WN2039
----
----
----
11:50
11:50
----
----
WN571
WN1354
----
----
----
----
----
11:50
----
WN1201
WN4585
----
----
----
11:55
11:55
----
----
WN1321
WN3109
12:05
12:05
12:05
----
----
----
12:05
WN2463
WN3293
12:15
12:15
12:15
13:05
13:05
----
12:15
WN1196
WN1496
----
----
----
12:25
12:25
----
----
WN701
WN130
----
----
----
----
----
12:40
----
WN2981
WN1637
----
----
----
12:50
12:50
----
----
WN27
WN1260
----
----
----
13:00
13:00
----
----
WN27
WN1111
----
----
----
13:00
13:00
----
----
WN3312
WN554
13:05
13:05
13:05
----
----
----
13:05
WN22
WN2973
----
----
----
13:20
13:20
----
----
WN964
WN2039
----
----
----
13:25
13:25
----
----
WN1637
WN1253
13:25
13:25
13:25
----
----
----
13:25
WN311
WN1647
13:50
13:50
13:50
----
----
----
13:50
WN1227
WN4071
----
----
----
13:50
13:50
----
----
WN1227
WN4703
----
----
----
13:50
13:50
----
----
WN3014
WN1533
----
----
----
14:05
14:05
----
----
WN33
WN1732
----
----
----
----
----
14:20
----
WN33
WN1260
----
----
----
14:30
14:30
----
----
WN33
WN1647
14:30
14:30
14:30
----
----
----
14:30
WN295
WN1647
----
----
----
14:40
14:40
----
----
WN1589
WN1647
----
----
----
14:55
14:55
----
----
WN1458
WN130
15:10
15:10
15:10
----
----
----
15:10
WN2535
WN1449
----
----
----
----
----
15:25
----
WN3917
WN1253
15:35
15:35
15:35
----
----
----
15:35
WN3260
WN4703
----
----
----
15:35
15:35
----
----
WN39
WN1732
16:00
16:00
16:00
16:00
16:00
----
16:00
WN39
WN1647
16:00
16:00
16:00
----
----
----
16:00
WN35
WN1732
----
----
----
----
----
16:15
----
WN3612
WN1647
----
----
----
16:50
16:50
----
----
WN45
WN1732
17:30
17:30
17:30
17:30
17:30
----
17:30
WN2231
WN3012
----
----
----
17:50
17:50
----
----
WN2695
WN1647
18:05
18:05
18:05
----
----
----
18:05
WN49
WN1732
18:30
18:30
18:30
18:30
18:30
----
18:30
SHOW RETURN SCHEDULE
CHECK PRICES FOR DAL - MDW

The timetable & schedule information was updated at 2024-12-13

Via Nashville with Southwest Airlines

  • Total flight time: 3h 50m - 8h 40m.
  • Low-cost airline
  • Dallas and Chicago are both Southwest Airlines focus cities.
  • 47 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 (winglets) Passenger/BBJ1
DAL
 
Via BNA
 
MDW
 
Flight
Mon
Jan 13
Tue
Jan 14
Wed
Jan 15
Thu
Jan 16
Fri
Jan 17
Sat
Jan 18
Sun
Jan 19
WN201
WN2332
----
----
----
----
----
06:00
----
WN201
WN4499
----
----
----
----
----
06:00
----
WN1859
WN2364
06:25
06:25
06:25
06:00
06:00
08:45
06:25
WN2819
WN3300
----
----
----
06:35
06:35
----
----
WN2007
WN198
----
----
----
06:45
06:45
----
----
WN2819
WN1119
----
----
----
----
----
07:00
----
WN2007
WN736
07:10
07:10
07:10
----
----
----
----
WN561
WN162
----
----
----
----
----
07:15
----
WN3
WN2630
07:30
07:30
07:30
----
----
----
----
WN561
WN1925
07:35
07:35
07:35
----
----
----
07:35
WN1077
WN1155
----
----
----
----
----
07:40
----
WN701
WN2847
----
----
----
07:50
07:50
----
----
WN1623
WN1471
----
----
----
07:55
07:55
----
----
WN1623
WN1791
----
----
----
07:55
07:55
----
----
WN1623
WN4877
08:15
08:15
08:15
----
----
----
08:15
WN7
WN2630
08:30
08:30
08:30
08:30
08:30
----
08:30
WN2016
WN198
----
----
----
08:30
08:30
----
----
WN9
WN2630
----
----
----
----
----
08:35
----
WN714
WN262
08:45
08:45
08:45
----
----
----
08:45
WN2016
WN3293
----
----
----
----
----
09:10
----
WN775
WN1471
----
----
----
09:35
09:35
----
----
WN1195
WN2434
----
----
----
----
----
09:45
----
WN15
WN2630
----
----
----
10:00
10:00
----
----
WN3118
WN1119
----
----
----
----
----
10:05
----
WN19
WN481
----
----
----
----
----
10:10
----
WN356
WN3109
10:30
10:30
10:30
----
----
----
10:30
WN1445
WN2913
10:40
10:40
10:40
----
----
----
10:40
WN652
WN4877
----
----
----
----
----
10:45
----
WN652
WN3079
----
----
----
----
----
10:45
----
WN2569
WN3079
10:45
10:45
10:45
----
----
----
10:45
WN652
WN3705
----
----
----
----
----
10:45
----
WN503
WN2434
----
----
----
11:00
11:00
----
----
WN2852
WN554
11:00
11:00
11:00
----
----
----
11:00
WN1754
WN4071
11:25
11:25
11:25
----
----
----
11:25
WN1754
WN3434
11:25
11:25
11:25
----
----
----
11:25
WN19
WN1260
11:30
11:30
11:30
----
----
----
11:30
WN19
WN1111
----
----
----
11:30
11:30
----
----
WN17
WN481
----
----
----
----
----
11:30
----
WN1445
WN2039
----
----
----
11:50
11:50
----
----
WN571
WN1354
----
----
----
----
----
11:50
----
WN1201
WN4585
----
----
----
11:55
11:55
----
----
WN1321
WN3109
12:05
12:05
12:05
----
----
----
12:05
WN2463
WN3293
12:15
12:15
12:15
13:05
13:05
----
12:15
WN1196
WN1496
----
----
----
12:25
12:25
----
----
WN701
WN130
----
----
----
----
----
12:40
----
WN2981
WN1637
----
----
----
12:50
12:50
----
----
WN27
WN1260
----
----
----
13:00
13:00
----
----
WN27
WN1111
----
----
----
13:00
13:00
----
----
WN3312
WN554
13:05
13:05
13:05
----
----
----
13:05
WN22
WN2973
----
----
----
13:20
13:20
----
----
WN964
WN2039
----
----
----
13:25
13:25
----
----
WN1637
WN1253
13:25
13:25
13:25
----
----
----
13:25
WN311
WN1647
13:50
13:50
13:50
----
----
----
13:50
WN1227
WN4071
----
----
----
13:50
13:50
----
----
WN1227
WN4703
----
----
----
13:50
13:50
----
----
WN3014
WN1533
----
----
----
14:05
14:05
----
----
WN33
WN1732
----
----
----
----
----
14:20
----
WN33
WN1260
----
----
----
14:30
14:30
----
----
WN33
WN1647
14:30
14:30
14:30
----
----
----
14:30
WN295
WN1647
----
----
----
14:40
14:40
----
----
WN1589
WN1647
----
----
----
14:55
14:55
----
----
WN1458
WN130
15:10
15:10
15:10
----
----
----
15:10
WN2535
WN1449
----
----
----
----
----
15:25
----
WN3917
WN1253
15:35
15:35
15:35
----
----
----
15:35
WN3260
WN4703
----
----
----
15:35
15:35
----
----
WN39
WN1732
16:00
16:00
16:00
16:00
16:00
----
16:00
WN39
WN1647
16:00
16:00
16:00
----
----
----
16:00
WN35
WN1732
----
----
----
----
----
16:15
----
WN3612
WN1647
----
----
----
16:50
16:50
----
----
WN45
WN1732
17:30
17:30
17:30
17:30
17:30
----
17:30
WN2231
WN3012
----
----
----
17:50
17:50
----
----
WN2695
WN1647
18:05
18:05
18:05
----
----
----
18:05
WN49
WN1732
18:30
18:30
18:30
18:30
18:30
----
18:30
SHOW RETURN SCHEDULE
CHECK PRICES FOR DAL - MDW

The timetable & schedule information was updated at 2024-12-13

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.
  • 37 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 (winglets) Passenger/BBJ1
DAL
 
Via STL
 
MDW
 
Flight
Mon
Jan 13
Tue
Jan 14
Wed
Jan 15
Thu
Jan 16
Fri
Jan 17
Sat
Jan 18
Sun
Jan 19
WN201
WN2332
----
----
----
----
----
06:00
----
WN201
WN4499
----
----
----
----
----
06:00
----
WN1859
WN2364
06:25
06:25
06:25
06:00
06:00
08:45
06:25
WN2819
WN3300
----
----
----
06:35
06:35
----
----
WN2007
WN198
----
----
----
06:45
06:45
----
----
WN2819
WN1119
----
----
----
----
----
07:00
----
WN2007
WN736
07:10
07:10
07:10
----
----
----
----
WN561
WN162
----
----
----
----
----
07:15
----
WN3
WN2630
07:30
07:30
07:30
----
----
----
----
WN561
WN1925
07:35
07:35
07:35
----
----
----
07:35
WN1077
WN1155
----
----
----
----
----
07:40
----
WN701
WN2847
----
----
----
07:50
07:50
----
----
WN1623
WN1471
----
----
----
07:55
07:55
----
----
WN1623
WN1791
----
----
----
07:55
07:55
----
----
WN1623
WN4877
08:15
08:15
08:15
----
----
----
08:15
WN7
WN2630
08:30
08:30
08:30
08:30
08:30
----
08:30
WN2016
WN198
----
----
----
08:30
08:30
----
----
WN9
WN2630
----
----
----
----
----
08:35
----
WN714
WN262
08:45
08:45
08:45
----
----
----
08:45
WN2016
WN3293
----
----
----
----
----
09:10
----
WN775
WN1471
----
----
----
09:35
09:35
----
----
WN1195
WN2434
----
----
----
----
----
09:45
----
WN15
WN2630
----
----
----
10:00
10:00
----
----
WN3118
WN1119
----
----
----
----
----
10:05
----
WN19
WN481
----
----
----
----
----
10:10
----
WN356
WN3109
10:30
10:30
10:30
----
----
----
10:30
WN1445
WN2913
10:40
10:40
10:40
----
----
----
10:40
WN652
WN4877
----
----
----
----
----
10:45
----
WN652
WN3079
----
----
----
----
----
10:45
----
WN2569
WN3079
10:45
10:45
10:45
----
----
----
10:45
WN652
WN3705
----
----
----
----
----
10:45
----
WN503
WN2434
----
----
----
11:00
11:00
----
----
WN2852
WN554
11:00
11:00
11:00
----
----
----
11:00
WN1754
WN4071
11:25
11:25
11:25
----
----
----
11:25
WN1754
WN3434
11:25
11:25
11:25
----
----
----
11:25
WN19
WN1260
11:30
11:30
11:30
----
----
----
11:30
WN19
WN1111
----
----
----
11:30
11:30
----
----
WN17
WN481
----
----
----
----
----
11:30
----
WN1445
WN2039
----
----
----
11:50
11:50
----
----
WN571
WN1354
----
----
----
----
----
11:50
----
WN1201
WN4585
----
----
----
11:55
11:55
----
----
WN1321
WN3109
12:05
12:05
12:05
----
----
----
12:05
WN2463
WN3293
12:15
12:15
12:15
13:05
13:05
----
12:15
WN1196
WN1496
----
----
----
12:25
12:25
----
----
WN701
WN130
----
----
----
----
----
12:40
----
WN2981
WN1637
----
----
----
12:50
12:50
----
----
WN27
WN1260
----
----
----
13:00
13:00
----
----
WN27
WN1111
----
----
----
13:00
13:00
----
----
WN3312
WN554
13:05
13:05
13:05
----
----
----
13:05
WN22
WN2973
----
----
----
13:20
13:20
----
----
WN964
WN2039
----
----
----
13:25
13:25
----
----
WN1637
WN1253
13:25
13:25
13:25
----
----
----
13:25
WN311
WN1647
13:50
13:50
13:50
----
----
----
13:50
WN1227
WN4071
----
----
----
13:50
13:50
----
----
WN1227
WN4703
----
----
----
13:50
13:50
----
----
WN3014
WN1533
----
----
----
14:05
14:05
----
----
WN33
WN1732
----
----
----
----
----
14:20
----
WN33
WN1260
----
----
----
14:30
14:30
----
----
WN33
WN1647
14:30
14:30
14:30
----
----
----
14:30
WN295
WN1647
----
----
----
14:40
14:40
----
----
WN1589
WN1647
----
----
----
14:55
14:55
----
----
WN1458
WN130
15:10
15:10
15:10
----
----
----
15:10
WN2535
WN1449
----
----
----
----
----
15:25
----
WN3917
WN1253
15:35
15:35
15:35
----
----
----
15:35
WN3260
WN4703
----
----
----
15:35
15:35
----
----
WN39
WN1732
16:00
16:00
16:00
16:00
16:00
----
16:00
WN39
WN1647
16:00
16:00
16:00
----
----
----
16:00
WN35
WN1732
----
----
----
----
----
16:15
----
WN3612
WN1647
----
----
----
16:50
16:50
----
----
WN45
WN1732
17:30
17:30
17:30
17:30
17:30
----
17:30
WN2231
WN3012
----
----
----
17:50
17:50
----
----
WN2695
WN1647
18:05
18:05
18:05
----
----
----
18:05
WN49
WN1732
18:30
18:30
18:30
18:30
18:30
----
18:30
SHOW RETURN SCHEDULE
CHECK PRICES FOR DAL - MDW

The timetable & schedule information was updated at 2024-12-13

Via Kansas City with Southwest Airlines

  • Total flight time: 3h 30m - 5h 55m.
  • Low-cost airline
  • Dallas and Chicago are both Southwest Airlines focus cities.
  • 35 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 (winglets) Passenger/BBJ1
DAL
 
Via MCI
 
MDW
 
Flight
Mon
Jan 13
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Jan 14
Wed
Jan 15
Thu
Jan 16
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Jan 19
WN201
WN2332
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06:00
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WN201
WN4499
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06:00
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WN1859
WN2364
06:25
06:25
06:25
06:00
06:00
08:45
06:25
WN2819
WN3300
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06:35
06:35
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WN2007
WN198
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06:45
06:45
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WN2819
WN1119
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07:00
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WN2007
WN736
07:10
07:10
07:10
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WN561
WN162
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07:15
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WN3
WN2630
07:30
07:30
07:30
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WN561
WN1925
07:35
07:35
07:35
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07:35
WN1077
WN1155
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07:40
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WN701
WN2847
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07:50
07:50
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WN1623
WN1471
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07:55
07:55
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WN1623
WN1791
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07:55
07:55
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WN1623
WN4877
08:15
08:15
08:15
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08:15
WN7
WN2630
08:30
08:30
08:30
08:30
08:30
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08:30
WN2016
WN198
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08:30
08:30
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WN9
WN2630
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08:35
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WN714
WN262
08:45
08:45
08:45
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08:45
WN2016
WN3293
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09:10
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WN775
WN1471
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09:35
09:35
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WN1195
WN2434
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09:45
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WN15
WN2630
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10:00
10:00
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WN3118
WN1119
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10:05
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WN19
WN481
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----
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----
----
10:10
----
WN356
WN3109
10:30
10:30
10:30
----
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10:30
WN1445
WN2913
10:40
10:40
10:40
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10:40
WN652
WN4877
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10:45
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WN652
WN3079
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10:45
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WN2569
WN3079
10:45
10:45
10:45
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10:45
WN652
WN3705
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10:45
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WN503
WN2434
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11:00
11:00
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WN2852
WN554
11:00
11:00
11:00
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11:00
WN1754
WN4071
11:25
11:25
11:25
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11:25
WN1754
WN3434
11:25
11:25
11:25
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11:25
WN19
WN1260
11:30
11:30
11:30
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11:30
WN19
WN1111
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11:30
11:30
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WN17
WN481
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11:30
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WN1445
WN2039
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11:50
11:50
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WN571
WN1354
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----
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----
----
11:50
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WN1201
WN4585
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11:55
11:55
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WN1321
WN3109
12:05
12:05
12:05
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12:05
WN2463
WN3293
12:15
12:15
12:15
13:05
13:05
----
12:15
WN1196
WN1496
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----
----
12:25
12:25
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----
WN701
WN130
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----
----
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12:40
----
WN2981
WN1637
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12:50
12:50
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----
WN27
WN1260
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----
----
13:00
13:00
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----
WN27
WN1111
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----
----
13:00
13:00
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WN3312
WN554
13:05
13:05
13:05
----
----
----
13:05
WN22
WN2973
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----
----
13:20
13:20
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----
WN964
WN2039
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----
13:25
13:25
----
----
WN1637
WN1253
13:25
13:25
13:25
----
----
----
13:25
WN311
WN1647
13:50
13:50
13:50
----
----
----
13:50
WN1227
WN4071
----
----
----
13:50
13:50
----
----
WN1227
WN4703
----
----
----
13:50
13:50
----
----
WN3014
WN1533
----
----
----
14:05
14:05
----
----
WN33
WN1732
----
----
----
----
----
14:20
----
WN33
WN1260
----
----
----
14:30
14:30
----
----
WN33
WN1647
14:30
14:30
14:30
----
----
----
14:30
WN295
WN1647
----
----
----
14:40
14:40
----
----
WN1589
WN1647
----
----
----
14:55
14:55
----
----
WN1458
WN130
15:10
15:10
15:10
----
----
----
15:10
WN2535
WN1449
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----
----
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15:25
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WN3917
WN1253
15:35
15:35
15:35
----
----
----
15:35
WN3260
WN4703
----
----
----
15:35
15:35
----
----
WN39
WN1732
16:00
16:00
16:00
16:00
16:00
----
16:00
WN39
WN1647
16:00
16:00
16:00
----
----
----
16:00
WN35
WN1732
----
----
----
----
----
16:15
----
WN3612
WN1647
----
----
----
16:50
16:50
----
----
WN45
WN1732
17:30
17:30
17:30
17:30
17:30
----
17:30
WN2231
WN3012
----
----
----
17:50
17:50
----
----
WN2695
WN1647
18:05
18:05
18:05
----
----
----
18:05
WN49
WN1732
18:30
18:30
18:30
18:30
18:30
----
18:30
SHOW RETURN SCHEDULE
CHECK PRICES FOR DAL - MDW

The timetable & schedule information was updated at 2024-12-13

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