Airlines with flights from Oakland to Chicago

Southwest is the only airline with non-stop flights from Metropolitan Oakland International to Midway International Airport and the flight time is 4 hours and 5 minutes.

Choose airline

Schedules

Non-stop with Southwest Airlines

  • Total flight time: 4 hours and 5 minutes
  • Low-cost airline
  • Oakland and Chicago are both Southwest Airlines focus cities.
  • 7 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
OAK
Direct
MDW

The timetable & schedule information was updated at 2025-01-15

Via Las Vegas with Southwest Airlines

  • Total flight time: 5h 45m - 11h 10m.
  • Low-cost airline
  • Oakland and Chicago are both Southwest Airlines focus cities.
  • 45 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
OAK
 
Via LAS
 
MDW
 
Flight
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Feb 3
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WN419
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WN4182
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WN671
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16:00
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SHOW RETURN SCHEDULE
CHECK PRICES FOR OAK - MDW

The timetable & schedule information was updated at 2025-01-15

Via Phoenix with Southwest Airlines

  • Total flight time: 5h 55m - 10h 50m.
  • Low-cost airline
  • Oakland and Chicago are both Southwest Airlines focus cities.
  • 37 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
OAK
 
Via PHX
 
MDW
 
Flight
Mon
Feb 3
Tue
Feb 4
Wed
Feb 5
Thu
Feb 6
Fri
Feb 7
Sat
Feb 8
Sun
Feb 9
WN329
WN503
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05:10
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WN1242
WN2461
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WN716
WN2756
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WN716
WN2337
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WN1354
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WN715
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WN4201
WN1966
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WN329
WN2497
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WN458
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WN805
WN2912
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WN1358
WN925
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WN4379
WN770
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WN762
WN2798
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WN814
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WN1159
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WN1451
WN4165
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WN5050
WN554
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WN1516
WN2912
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WN3150
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WN3199
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WN887
WN419
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WN1413
WN2497
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WN1173
WN2798
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WN3929
WN340
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WN419
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WN840
WN3150
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WN840
WN2054
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WN2046
WN1533
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WN4182
WN4514
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WN4182
WN419
09:50
09:50
09:50
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WN2046
WN3150
10:05
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WN1167
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WN208
WN3150
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WN4975
WN3150
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WN2217
WN2749
11:10
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WN4975
WN340
11:10
11:10
11:10
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WN1496
WN1729
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11:25
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WN1352
WN1397
12:15
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12:15
WN969
WN2749
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WN969
WN1678
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12:15
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WN3083
WN1729
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WN4670
WN1397
13:10
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WN2758
WN2054
13:15
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13:25
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WN671
WN1397
13:15
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13:15
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WN5109
WN340
13:15
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WN5109
WN4758
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13:15
WN175
WN1678
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13:15
13:15
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WN3070
WN4372
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13:20
13:20
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WN489
WN1506
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13:20
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WN489
WN1678
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13:20
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WN2758
WN3960
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13:25
13:25
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WN208
WN1506
13:50
13:50
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----
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WN4015
WN2668
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WN1716
WN2668
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13:55
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WN5109
WN4104
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14:00
14:00
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WN844
WN1397
14:50
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14:50
WN4718
WN4188
15:35
15:35
15:35
----
----
----
15:35
WN1673
WN4188
----
----
----
16:00
16:00
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR OAK - MDW

The timetable & schedule information was updated at 2025-01-15

Via Denver with Southwest Airlines

  • Total flight time: 5h 30m - 11h 05m.
  • Low-cost airline
  • Oakland and Chicago are both Southwest Airlines focus cities.
  • 27 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
OAK
 
Via DEN
 
MDW
 
Flight
Mon
Feb 3
Tue
Feb 4
Wed
Feb 5
Thu
Feb 6
Fri
Feb 7
Sat
Feb 8
Sun
Feb 9
WN329
WN503
----
----
----
----
----
05:10
----
WN1242
WN2461
----
----
----
05:25
05:25
----
----
WN716
WN2756
05:35
05:35
05:35
----
----
----
05:35
WN716
WN2337
05:35
05:35
05:35
----
----
----
05:35
WN361
WN1354
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----
----
----
----
05:55
----
WN361
WN715
----
----
----
----
----
05:55
----
WN361
WN2080
----
----
----
----
----
05:55
----
WN157
WN2337
----
----
----
----
----
06:05
----
WN1261
WN2497
----
----
----
06:10
06:10
----
----
WN361
WN1036
06:25
06:25
06:25
----
----
----
06:25
WN361
WN1410
06:25
06:25
06:25
----
----
----
06:25
WN1207
WN1036
----
----
----
06:35
06:35
----
----
WN4201
WN1966
----
----
----
----
----
06:40
----
WN329
WN2497
06:40
06:40
06:40
----
----
----
06:50
WN4201
WN458
06:45
06:45
06:45
----
----
----
06:45
WN805
WN2912
----
----
----
06:50
06:50
----
----
WN1358
WN925
06:50
06:50
06:50
----
----
----
----
WN4379
WN770
06:55
06:55
06:55
----
----
----
06:55
WN762
WN2798
----
----
----
06:55
06:55
----
----
WN762
WN3708
----
----
----
----
----
07:30
----
WN814
WN715
----
----
----
----
----
07:35
----
WN2466
WN2564
08:15
08:15
08:15
----
----
----
08:05
WN1721
WN2798
----
----
----
08:10
08:10
----
----
WN1159
WN1036
----
----
----
08:15
08:15
----
----
WN1159
WN1277
----
----
----
08:15
08:15
----
----
WN1159
WN1533
----
----
----
08:15
08:15
----
----
WN1451
WN4165
08:15
08:15
08:15
----
----
----
----
WN5050
WN554
08:35
08:35
08:35
----
----
----
08:35
WN1516
WN2912
----
----
----
08:45
08:45
----
----
WN3372
WN1786
----
----
----
08:45
08:45
----
----
WN3372
WN3150
----
----
----
08:45
08:45
----
----
WN3199
WN1966
08:45
08:45
08:45
08:45
----
----
08:45
WN887
WN419
----
----
----
----
----
08:45
----
WN1187
WN3423
----
----
----
08:50
08:50
----
----
WN1187
WN2497
----
----
----
08:50
08:50
----
----
WN1413
WN3784
08:55
08:55
08:55
----
----
----
08:55
WN1413
WN2497
08:55
08:55
08:55
----
----
----
08:55
WN1067
WN925
09:05
09:05
09:05
09:00
09:00
----
09:05
WN1173
WN2798
----
----
----
09:05
09:05
----
----
WN3929
WN340
09:15
09:15
09:15
----
----
----
----
WN3929
WN4758
----
----
----
----
----
----
09:15
WN1279
WN2912
----
----
----
09:20
09:20
----
----
WN4969
WN4514
----
----
----
----
----
09:30
----
WN4969
WN419
----
----
----
----
----
09:30
----
WN840
WN3150
----
----
----
09:40
09:40
----
----
WN840
WN2054
----
----
----
09:40
09:40
----
----
WN2046
WN1533
----
----
----
09:45
09:45
----
----
WN4182
WN4514
09:50
09:50
09:50
----
----
----
09:50
WN4182
WN419
09:50
09:50
09:50
----
----
----
09:50
WN2046
WN3150
10:05
10:05
10:05
----
----
----
10:05
WN2560
WN1729
----
----
----
----
----
10:40
----
WN2560
WN1167
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----
----
----
----
10:40
----
WN2637
WN2835
----
----
----
----
----
11:00
----
WN208
WN3150
----
----
----
11:00
11:00
----
----
WN4975
WN3150
11:10
11:10
11:10
----
----
----
11:10
WN2217
WN2749
11:10
11:10
11:10
----
----
----
11:10
WN4975
WN340
11:10
11:10
11:10
----
----
----
----
WN1496
WN1729
----
----
----
----
----
11:25
----
WN1352
WN1397
12:15
12:15
12:15
----
----
----
12:15
WN969
WN2749
----
----
----
12:15
12:15
----
----
WN969
WN1678
----
----
----
12:15
12:15
----
----
WN3083
WN1729
----
----
----
----
----
12:45
----
WN4670
WN1397
13:10
13:10
13:10
----
----
----
13:10
WN2758
WN2054
13:15
13:15
13:15
13:25
13:25
----
13:15
WN671
WN1397
13:15
13:15
13:15
----
----
----
13:15
WN5109
WN340
13:15
13:15
13:15
----
----
----
----
WN5109
WN4758
----
----
----
----
----
----
13:15
WN175
WN1678
----
----
----
13:15
13:15
----
----
WN3070
WN4372
----
----
----
13:20
13:20
----
----
WN489
WN1506
----
----
----
13:20
13:20
----
----
WN489
WN1678
----
----
----
13:20
13:20
----
----
WN2758
WN3960
----
----
----
13:25
13:25
----
----
WN208
WN1506
13:50
13:50
13:50
----
----
----
13:50
WN4015
WN2668
----
----
----
----
----
13:50
----
WN1716
WN2668
----
----
----
----
----
13:55
----
WN5109
WN4104
----
----
----
14:00
14:00
----
----
WN844
WN1397
14:50
14:50
14:50
----
----
----
14:50
WN4718
WN4188
15:35
15:35
15:35
----
----
----
15:35
WN1673
WN4188
----
----
----
16:00
16:00
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR OAK - MDW

The timetable & schedule information was updated at 2025-01-15

Via Los Angeles with Southwest Airlines

  • Total flight time: 6h 10m - 9h 40m.
  • Low-cost airline
  • Oakland and Chicago are both Southwest Airlines focus cities.
  • 19 flights per week
  • Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
OAK
 
Via LAX
 
MDW
 
Flight
Mon
Feb 3
Tue
Feb 4
Wed
Feb 5
Thu
Feb 6
Fri
Feb 7
Sat
Feb 8
Sun
Feb 9
WN329
WN503
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----
----
----
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05:10
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WN1242
WN2461
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05:25
05:25
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----
WN716
WN2756
05:35
05:35
05:35
----
----
----
05:35
WN716
WN2337
05:35
05:35
05:35
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----
----
05:35
WN361
WN1354
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----
----
----
----
05:55
----
WN361
WN715
----
----
----
----
----
05:55
----
WN361
WN2080
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----
----
----
----
05:55
----
WN157
WN2337
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----
----
----
----
06:05
----
WN1261
WN2497
----
----
----
06:10
06:10
----
----
WN361
WN1036
06:25
06:25
06:25
----
----
----
06:25
WN361
WN1410
06:25
06:25
06:25
----
----
----
06:25
WN1207
WN1036
----
----
----
06:35
06:35
----
----
WN4201
WN1966
----
----
----
----
----
06:40
----
WN329
WN2497
06:40
06:40
06:40
----
----
----
06:50
WN4201
WN458
06:45
06:45
06:45
----
----
----
06:45
WN805
WN2912
----
----
----
06:50
06:50
----
----
WN1358
WN925
06:50
06:50
06:50
----
----
----
----
WN4379
WN770
06:55
06:55
06:55
----
----
----
06:55
WN762
WN2798
----
----
----
06:55
06:55
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----
WN762
WN3708
----
----
----
----
----
07:30
----
WN814
WN715
----
----
----
----
----
07:35
----
WN2466
WN2564
08:15
08:15
08:15
----
----
----
08:05
WN1721
WN2798
----
----
----
08:10
08:10
----
----
WN1159
WN1036
----
----
----
08:15
08:15
----
----
WN1159
WN1277
----
----
----
08:15
08:15
----
----
WN1159
WN1533
----
----
----
08:15
08:15
----
----
WN1451
WN4165
08:15
08:15
08:15
----
----
----
----
WN5050
WN554
08:35
08:35
08:35
----
----
----
08:35
WN1516
WN2912
----
----
----
08:45
08:45
----
----
WN3372
WN1786
----
----
----
08:45
08:45
----
----
WN3372
WN3150
----
----
----
08:45
08:45
----
----
WN3199
WN1966
08:45
08:45
08:45
08:45
----
----
08:45
WN887
WN419
----
----
----
----
----
08:45
----
WN1187
WN3423
----
----
----
08:50
08:50
----
----
WN1187
WN2497
----
----
----
08:50
08:50
----
----
WN1413
WN3784
08:55
08:55
08:55
----
----
----
08:55
WN1413
WN2497
08:55
08:55
08:55
----
----
----
08:55
WN1067
WN925
09:05
09:05
09:05
09:00
09:00
----
09:05
WN1173
WN2798
----
----
----
09:05
09:05
----
----
WN3929
WN340
09:15
09:15
09:15
----
----
----
----
WN3929
WN4758
----
----
----
----
----
----
09:15
WN1279
WN2912
----
----
----
09:20
09:20
----
----
WN4969
WN4514
----
----
----
----
----
09:30
----
WN4969
WN419
----
----
----
----
----
09:30
----
WN840
WN3150
----
----
----
09:40
09:40
----
----
WN840
WN2054
----
----
----
09:40
09:40
----
----
WN2046
WN1533
----
----
----
09:45
09:45
----
----
WN4182
WN4514
09:50
09:50
09:50
----
----
----
09:50
WN4182
WN419
09:50
09:50
09:50
----
----
----
09:50
WN2046
WN3150
10:05
10:05
10:05
----
----
----
10:05
WN2560
WN1729
----
----
----
----
----
10:40
----
WN2560
WN1167
----
----
----
----
----
10:40
----
WN2637
WN2835
----
----
----
----
----
11:00
----
WN208
WN3150
----
----
----
11:00
11:00
----
----
WN4975
WN3150
11:10
11:10
11:10
----
----
----
11:10
WN2217
WN2749
11:10
11:10
11:10
----
----
----
11:10
WN4975
WN340
11:10
11:10
11:10
----
----
----
----
WN1496
WN1729
----
----
----
----
----
11:25
----
WN1352
WN1397
12:15
12:15
12:15
----
----
----
12:15
WN969
WN2749
----
----
----
12:15
12:15
----
----
WN969
WN1678
----
----
----
12:15
12:15
----
----
WN3083
WN1729
----
----
----
----
----
12:45
----
WN4670
WN1397
13:10
13:10
13:10
----
----
----
13:10
WN2758
WN2054
13:15
13:15
13:15
13:25
13:25
----
13:15
WN671
WN1397
13:15
13:15
13:15
----
----
----
13:15
WN5109
WN340
13:15
13:15
13:15
----
----
----
----
WN5109
WN4758
----
----
----
----
----
----
13:15
WN175
WN1678
----
----
----
13:15
13:15
----
----
WN3070
WN4372
----
----
----
13:20
13:20
----
----
WN489
WN1506
----
----
----
13:20
13:20
----
----
WN489
WN1678
----
----
----
13:20
13:20
----
----
WN2758
WN3960
----
----
----
13:25
13:25
----
----
WN208
WN1506
13:50
13:50
13:50
----
----
----
13:50
WN4015
WN2668
----
----
----
----
----
13:50
----
WN1716
WN2668
----
----
----
----
----
13:55
----
WN5109
WN4104
----
----
----
14:00
14:00
----
----
WN844
WN1397
14:50
14:50
14:50
----
----
----
14:50
WN4718
WN4188
15:35
15:35
15:35
----
----
----
15:35
WN1673
WN4188
----
----
----
16:00
16:00
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR OAK - MDW

The timetable & schedule information was updated at 2025-01-15

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