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.
  • 11 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
OAK
Direct
MDW

The timetable & schedule information was updated at 2024-10-16

Via Las Vegas with Southwest Airlines

  • Total flight time: 5h 45m - 11h 05m.
  • Low-cost airline
  • Oakland and Chicago are both Southwest Airlines focus cities.
  • 50 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
OAK
 
Via LAS
 
MDW
 
Flight
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SHOW RETURN SCHEDULE
CHECK PRICES FOR OAK - MDW

The timetable & schedule information was updated at 2024-10-16

Via Denver with Southwest Airlines

  • Total flight time: 5h 30m - 10h 40m.
  • Low-cost airline
  • Oakland and Chicago are both Southwest Airlines focus cities.
  • 28 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
OAK
 
Via DEN
 
MDW
 
Flight
Mon
Dec 2
Tue
Dec 3
Wed
Dec 4
Thu
Dec 5
Fri
Dec 6
Sat
Dec 7
Sun
Dec 8
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09:55
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10:05
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WN2197
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----
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10:55
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----
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----
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----
----
----
----
12:10
----
WN2217
WN712
----
12:15
12:15
12:15
12:15
----
----
WN2472
WN1397
----
----
----
----
----
----
12:15
WN1496
WN2054
----
----
----
----
----
12:40
----
WN2046
WN2668
13:00
----
----
----
----
----
----
WN2758
WN3150
----
----
----
----
----
----
13:00
WN2758
WN2316
----
----
----
----
----
----
13:00
WN2472
WN869
----
----
----
----
----
13:00
----
WN733
WN1506
----
13:10
13:10
13:10
13:10
----
----
WN857
WN207
----
----
----
----
----
----
13:45
WN2758
WN2054
----
13:45
13:45
13:45
13:45
----
----
WN3406
WN4514
----
----
----
----
----
----
14:00
WN2758
WN2668
14:30
----
----
----
----
14:05
----
WN2758
WN443
14:30
----
----
----
----
----
----
WN4280
WN2668
----
----
----
----
----
----
15:15
WN1471
WN2533
15:20
----
----
----
----
----
----
WN346
WN2668
----
----
----
----
----
15:35
----
WN3283
WN712
----
----
----
----
----
----
15:35
WN1362
WN3242
15:40
----
----
----
----
----
----
WN3711
WN1966
15:40
----
----
----
----
----
----
WN2298
WN443
15:50
----
----
----
----
----
----
WN2256
WN3765
15:50
----
----
----
----
----
----
WN2256
WN3423
15:50
----
----
----
----
----
----
WN2298
WN3242
15:50
----
----
----
----
----
----
WN2760
WN2316
----
----
----
----
----
----
15:55
WN3452
WN4188
----
16:25
16:25
16:25
16:25
----
----
WN5814
WN3078
16:40
----
----
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR OAK - MDW

The timetable & schedule information was updated at 2024-10-16

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.
  • 22 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
OAK
 
Via LAX
 
MDW
 
Flight
Mon
Dec 2
Tue
Dec 3
Wed
Dec 4
Thu
Dec 5
Fri
Dec 6
Sat
Dec 7
Sun
Dec 8
WN3877
WN4546
05:00
----
----
----
----
----
----
WN329
WN983
----
----
----
----
----
05:05
----
WN329
WN1354
----
----
----
----
----
05:05
----
WN1542
WN2337
05:10
----
----
----
----
----
----
WN329
WN648
----
----
----
----
----
----
05:15
WN329
WN1412
----
----
----
----
----
----
05:15
WN5001
WN2389
05:20
----
----
----
----
----
----
WN361
WN3294
----
----
----
----
----
----
05:20
WN5001
WN2497
05:20
----
----
----
----
----
----
WN329
WN709
----
05:25
05:25
05:25
05:25
----
----
WN329
WN2443
----
05:25
05:25
05:25
05:25
----
----
WN3074
WN1741
----
----
----
----
----
----
05:30
WN3191
WN277
05:30
----
----
----
----
----
----
WN157
WN1406
----
----
----
----
----
05:30
----
WN361
WN715
----
----
----
----
----
05:40
----
WN423
WN2912
----
----
----
----
----
----
05:55
WN361
WN2687
----
06:00
06:00
06:00
06:00
----
----
WN3872
WN1472
06:00
----
----
----
----
----
----
WN2331
WN4289
----
----
----
----
----
----
06:05
WN2331
WN925
----
----
----
----
----
----
06:05
WN887
WN4289
----
----
----
----
----
----
06:45
WN255
WN2364
----
----
----
----
----
06:45
----
WN887
WN2773
----
----
----
----
----
06:55
----
WN762
WN2019
----
----
----
----
----
07:05
----
WN4201
WN1966
----
07:05
07:05
07:05
07:05
----
----
WN4201
WN3199
----
----
----
----
----
07:10
----
WN4201
WN2541
----
----
----
----
----
07:10
----
WN157
WN2337
----
07:10
07:10
07:10
07:10
----
----
WN887
WN1397
----
07:15
07:15
07:15
07:15
----
----
WN814
WN4289
----
----
----
----
----
----
07:20
WN814
WN2756
----
----
----
----
----
----
07:20
WN814
WN3969
----
----
----
----
----
----
07:20
WN5259
WN3079
----
----
----
----
----
07:20
----
WN814
WN3294
----
----
----
----
----
----
07:20
WN814
WN1155
08:00
----
----
----
----
----
----
WN814
WN1228
08:00
----
----
----
----
----
----
WN814
WN463
08:00
----
----
----
----
----
----
WN814
WN197
08:00
----
----
----
----
----
----
WN411
WN3319
----
----
----
----
----
----
08:05
WN329
WN1217
08:05
----
----
----
----
----
----
WN1173
WN737
----
08:05
08:05
08:05
08:05
----
----
WN329
WN223
08:05
----
----
----
----
----
----
WN329
WN2710
08:05
----
----
----
----
----
----
WN329
WN1396
08:05
----
----
----
----
----
----
WN329
WN2497
08:05
----
----
----
----
----
----
WN329
WN3179
08:05
----
----
----
----
----
----
WN3020
WN3049
----
08:10
08:10
08:10
08:10
----
----
WN1560
WN1729
----
08:15
08:15
08:15
08:15
----
----
WN2820
WN5843
----
----
----
----
----
----
08:30
WN2820
WN2912
----
----
----
----
----
----
08:30
WN1413
WN2710
----
----
----
----
----
----
08:35
WN1413
WN2551
----
----
----
----
----
----
08:35
WN3565
WN2497
----
08:35
08:35
08:35
08:35
----
----
WN1413
WN1017
----
----
----
----
----
----
08:35
WN3565
WN2353
----
08:35
08:35
08:35
08:35
----
----
WN1413
WN1793
----
----
----
----
----
----
08:35
WN1451
WN4289
----
----
----
----
----
----
08:40
WN1451
WN2756
----
----
----
----
----
----
08:40
WN1451
WN4418
----
----
----
----
----
----
08:40
WN1451
WN3969
----
----
----
----
----
----
08:40
WN863
WN343
08:45
----
----
----
----
----
----
WN1279
WN130
----
----
----
----
----
08:45
----
WN2901
WN2773
----
----
----
----
----
----
08:45
WN863
WN4514
08:45
----
----
----
----
----
----
WN4075
WN1966
----
----
----
----
----
----
08:50
WN197
WN3511
08:50
----
----
----
----
----
----
WN2078
WN419
----
----
----
----
----
----
08:55
WN4701
WN1966
----
08:55
08:55
08:55
08:55
----
----
WN1170
WN4514
08:55
----
----
----
----
----
----
WN2864
WN3423
----
----
----
----
----
----
09:00
WN1358
WN5305
----
----
----
----
----
----
09:00
WN2263
WN4928
----
09:00
09:00
09:00
09:00
----
----
WN1716
WN419
----
----
----
----
----
09:00
----
WN2046
WN2541
----
----
----
----
----
09:00
----
WN4182
WN130
----
----
----
----
----
09:20
----
WN1173
WN2216
09:55
----
----
----
----
----
----
WN843
WN1980
10:05
----
----
----
----
----
----
WN111
WN2749
----
----
----
----
----
----
10:05
WN849
WN2912
----
10:05
10:05
10:05
10:05
----
----
WN3083
WN419
----
10:15
10:15
10:15
10:15
----
----
WN3083
WN207
----
10:15
10:15
10:15
10:15
----
----
WN2874
WN1383
----
----
----
----
----
----
10:20
WN2046
WN3319
----
----
----
----
----
----
10:35
WN3438
WN3511
10:35
----
----
----
----
----
----
WN1413
WN1452
----
----
----
----
----
10:35
----
WN2197
WN207
----
10:55
10:55
10:55
10:55
----
----
WN1974
WN2216
10:55
----
----
----
----
----
----
WN2046
WN3150
----
11:00
11:00
11:00
11:00
----
----
WN1862
WN925
11:00
----
----
----
----
----
----
WN2077
WN2773
11:35
----
----
----
----
----
11:05
WN2217
WN2749
----
----
----
----
----
----
11:10
WN2810
WN419
----
----
----
----
----
11:10
----
WN1974
WN1383
----
----
----
----
----
----
11:15
WN1067
WN1276
----
11:25
11:25
11:25
11:25
----
----
WN294
WN343
11:40
----
----
----
----
----
----
WN294
WN1389
11:40
----
----
----
----
----
----
WN4805
WN4042
----
----
----
----
----
----
11:50
WN1413
WN1397
11:50
----
----
----
----
----
----
WN4861
WN1167
----
----
----
----
----
11:55
----
WN184
WN3150
----
----
----
----
----
----
12:00
WN2217
WN2461
----
----
----
----
----
12:10
----
WN2217
WN712
----
12:15
12:15
12:15
12:15
----
----
WN2472
WN1397
----
----
----
----
----
----
12:15
WN1496
WN2054
----
----
----
----
----
12:40
----
WN2046
WN2668
13:00
----
----
----
----
----
----
WN2758
WN3150
----
----
----
----
----
----
13:00
WN2758
WN2316
----
----
----
----
----
----
13:00
WN2472
WN869
----
----
----
----
----
13:00
----
WN733
WN1506
----
13:10
13:10
13:10
13:10
----
----
WN857
WN207
----
----
----
----
----
----
13:45
WN2758
WN2054
----
13:45
13:45
13:45
13:45
----
----
WN3406
WN4514
----
----
----
----
----
----
14:00
WN2758
WN2668
14:30
----
----
----
----
14:05
----
WN2758
WN443
14:30
----
----
----
----
----
----
WN4280
WN2668
----
----
----
----
----
----
15:15
WN1471
WN2533
15:20
----
----
----
----
----
----
WN346
WN2668
----
----
----
----
----
15:35
----
WN3283
WN712
----
----
----
----
----
----
15:35
WN1362
WN3242
15:40
----
----
----
----
----
----
WN3711
WN1966
15:40
----
----
----
----
----
----
WN2298
WN443
15:50
----
----
----
----
----
----
WN2256
WN3765
15:50
----
----
----
----
----
----
WN2256
WN3423
15:50
----
----
----
----
----
----
WN2298
WN3242
15:50
----
----
----
----
----
----
WN2760
WN2316
----
----
----
----
----
----
15:55
WN3452
WN4188
----
16:25
16:25
16:25
16:25
----
----
WN5814
WN3078
16:40
----
----
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR OAK - MDW

The timetable & schedule information was updated at 2024-10-16

Via Phoenix with Southwest Airlines

  • Total flight time: 5h 50m - 11h 25m.
  • Low-cost airline
  • Oakland and Chicago are both Southwest Airlines focus cities.
  • 22 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 (winglets) Passenger/BBJ1
    Boeing 737MAX 8 Passenger
OAK
 
Via PHX
 
MDW
 
Flight
Mon
Dec 2
Tue
Dec 3
Wed
Dec 4
Thu
Dec 5
Fri
Dec 6
Sat
Dec 7
Sun
Dec 8
WN3877
WN4546
05:00
----
----
----
----
----
----
WN329
WN983
----
----
----
----
----
05:05
----
WN329
WN1354
----
----
----
----
----
05:05
----
WN1542
WN2337
05:10
----
----
----
----
----
----
WN329
WN648
----
----
----
----
----
----
05:15
WN329
WN1412
----
----
----
----
----
----
05:15
WN5001
WN2389
05:20
----
----
----
----
----
----
WN361
WN3294
----
----
----
----
----
----
05:20
WN5001
WN2497
05:20
----
----
----
----
----
----
WN329
WN709
----
05:25
05:25
05:25
05:25
----
----
WN329
WN2443
----
05:25
05:25
05:25
05:25
----
----
WN3074
WN1741
----
----
----
----
----
----
05:30
WN3191
WN277
05:30
----
----
----
----
----
----
WN157
WN1406
----
----
----
----
----
05:30
----
WN361
WN715
----
----
----
----
----
05:40
----
WN423
WN2912
----
----
----
----
----
----
05:55
WN361
WN2687
----
06:00
06:00
06:00
06:00
----
----
WN3872
WN1472
06:00
----
----
----
----
----
----
WN2331
WN4289
----
----
----
----
----
----
06:05
WN2331
WN925
----
----
----
----
----
----
06:05
WN887
WN4289
----
----
----
----
----
----
06:45
WN255
WN2364
----
----
----
----
----
06:45
----
WN887
WN2773
----
----
----
----
----
06:55
----
WN762
WN2019
----
----
----
----
----
07:05
----
WN4201
WN1966
----
07:05
07:05
07:05
07:05
----
----
WN4201
WN3199
----
----
----
----
----
07:10
----
WN4201
WN2541
----
----
----
----
----
07:10
----
WN157
WN2337
----
07:10
07:10
07:10
07:10
----
----
WN887
WN1397
----
07:15
07:15
07:15
07:15
----
----
WN814
WN4289
----
----
----
----
----
----
07:20
WN814
WN2756
----
----
----
----
----
----
07:20
WN814
WN3969
----
----
----
----
----
----
07:20
WN5259
WN3079
----
----
----
----
----
07:20
----
WN814
WN3294
----
----
----
----
----
----
07:20
WN814
WN1155
08:00
----
----
----
----
----
----
WN814
WN1228
08:00
----
----
----
----
----
----
WN814
WN463
08:00
----
----
----
----
----
----
WN814
WN197
08:00
----
----
----
----
----
----
WN411
WN3319
----
----
----
----
----
----
08:05
WN329
WN1217
08:05
----
----
----
----
----
----
WN1173
WN737
----
08:05
08:05
08:05
08:05
----
----
WN329
WN223
08:05
----
----
----
----
----
----
WN329
WN2710
08:05
----
----
----
----
----
----
WN329
WN1396
08:05
----
----
----
----
----
----
WN329
WN2497
08:05
----
----
----
----
----
----
WN329
WN3179
08:05
----
----
----
----
----
----
WN3020
WN3049
----
08:10
08:10
08:10
08:10
----
----
WN1560
WN1729
----
08:15
08:15
08:15
08:15
----
----
WN2820
WN5843
----
----
----
----
----
----
08:30
WN2820
WN2912
----
----
----
----
----
----
08:30
WN1413
WN2710
----
----
----
----
----
----
08:35
WN1413
WN2551
----
----
----
----
----
----
08:35
WN3565
WN2497
----
08:35
08:35
08:35
08:35
----
----
WN1413
WN1017
----
----
----
----
----
----
08:35
WN3565
WN2353
----
08:35
08:35
08:35
08:35
----
----
WN1413
WN1793
----
----
----
----
----
----
08:35
WN1451
WN4289
----
----
----
----
----
----
08:40
WN1451
WN2756
----
----
----
----
----
----
08:40
WN1451
WN4418
----
----
----
----
----
----
08:40
WN1451
WN3969
----
----
----
----
----
----
08:40
WN863
WN343
08:45
----
----
----
----
----
----
WN1279
WN130
----
----
----
----
----
08:45
----
WN2901
WN2773
----
----
----
----
----
----
08:45
WN863
WN4514
08:45
----
----
----
----
----
----
WN4075
WN1966
----
----
----
----
----
----
08:50
WN197
WN3511
08:50
----
----
----
----
----
----
WN2078
WN419
----
----
----
----
----
----
08:55
WN4701
WN1966
----
08:55
08:55
08:55
08:55
----
----
WN1170
WN4514
08:55
----
----
----
----
----
----
WN2864
WN3423
----
----
----
----
----
----
09:00
WN1358
WN5305
----
----
----
----
----
----
09:00
WN2263
WN4928
----
09:00
09:00
09:00
09:00
----
----
WN1716
WN419
----
----
----
----
----
09:00
----
WN2046
WN2541
----
----
----
----
----
09:00
----
WN4182
WN130
----
----
----
----
----
09:20
----
WN1173
WN2216
09:55
----
----
----
----
----
----
WN843
WN1980
10:05
----
----
----
----
----
----
WN111
WN2749
----
----
----
----
----
----
10:05
WN849
WN2912
----
10:05
10:05
10:05
10:05
----
----
WN3083
WN419
----
10:15
10:15
10:15
10:15
----
----
WN3083
WN207
----
10:15
10:15
10:15
10:15
----
----
WN2874
WN1383
----
----
----
----
----
----
10:20
WN2046
WN3319
----
----
----
----
----
----
10:35
WN3438
WN3511
10:35
----
----
----
----
----
----
WN1413
WN1452
----
----
----
----
----
10:35
----
WN2197
WN207
----
10:55
10:55
10:55
10:55
----
----
WN1974
WN2216
10:55
----
----
----
----
----
----
WN2046
WN3150
----
11:00
11:00
11:00
11:00
----
----
WN1862
WN925
11:00
----
----
----
----
----
----
WN2077
WN2773
11:35
----
----
----
----
----
11:05
WN2217
WN2749
----
----
----
----
----
----
11:10
WN2810
WN419
----
----
----
----
----
11:10
----
WN1974
WN1383
----
----
----
----
----
----
11:15
WN1067
WN1276
----
11:25
11:25
11:25
11:25
----
----
WN294
WN343
11:40
----
----
----
----
----
----
WN294
WN1389
11:40
----
----
----
----
----
----
WN4805
WN4042
----
----
----
----
----
----
11:50
WN1413
WN1397
11:50
----
----
----
----
----
----
WN4861
WN1167
----
----
----
----
----
11:55
----
WN184
WN3150
----
----
----
----
----
----
12:00
WN2217
WN2461
----
----
----
----
----
12:10
----
WN2217
WN712
----
12:15
12:15
12:15
12:15
----
----
WN2472
WN1397
----
----
----
----
----
----
12:15
WN1496
WN2054
----
----
----
----
----
12:40
----
WN2046
WN2668
13:00
----
----
----
----
----
----
WN2758
WN3150
----
----
----
----
----
----
13:00
WN2758
WN2316
----
----
----
----
----
----
13:00
WN2472
WN869
----
----
----
----
----
13:00
----
WN733
WN1506
----
13:10
13:10
13:10
13:10
----
----
WN857
WN207
----
----
----
----
----
----
13:45
WN2758
WN2054
----
13:45
13:45
13:45
13:45
----
----
WN3406
WN4514
----
----
----
----
----
----
14:00
WN2758
WN2668
14:30
----
----
----
----
14:05
----
WN2758
WN443
14:30
----
----
----
----
----
----
WN4280
WN2668
----
----
----
----
----
----
15:15
WN1471
WN2533
15:20
----
----
----
----
----
----
WN346
WN2668
----
----
----
----
----
15:35
----
WN3283
WN712
----
----
----
----
----
----
15:35
WN1362
WN3242
15:40
----
----
----
----
----
----
WN3711
WN1966
15:40
----
----
----
----
----
----
WN2298
WN443
15:50
----
----
----
----
----
----
WN2256
WN3765
15:50
----
----
----
----
----
----
WN2256
WN3423
15:50
----
----
----
----
----
----
WN2298
WN3242
15:50
----
----
----
----
----
----
WN2760
WN2316
----
----
----
----
----
----
15:55
WN3452
WN4188
----
16:25
16:25
16:25
16:25
----
----
WN5814
WN3078
16:40
----
----
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR OAK - MDW

The timetable & schedule information was updated at 2024-10-16

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