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.

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Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 4 hours
  • Low-cost airline
  • Oakland and Chicago are both Southwest Airlines focus cities.
  • 13 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
OAK
Direct
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
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Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
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Aug 9
WN2744
05:10
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WN2671
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05:20
05:20
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WN4295
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05:25
WN3816
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10:35
10:35
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WN2986
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23:55
23:55
23:55
23:55
23:55
23:55
WN3059
23:55
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SHOW RETURN SCHEDULE
CHECK PRICES FOR OAK - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Denver with Southwest Airlines

  • Total flight time: 5h 25m - 10h 30m.
  • Low-cost airline
  • Oakland and Chicago are both Southwest Airlines focus cities.
  • 171 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
OAK
 
Via DEN
 
MDW
 
Flight
Mon
Aug 3
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Aug 6
Fri
Aug 7
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Aug 8
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Aug 9
WN3397
WN1601
05:05
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WN3041
WN755
05:45
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WN1595
WN1428
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06:00
06:00
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WN1921
WN1561
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06:10
WN2967
WN4021
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06:25
WN2967
WN1428
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06:50
06:50
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WN2967
WN523
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07:00
07:00
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WN2967
WN450
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07:05
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WN3042
WN1601
08:20
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WN1359
WN1428
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08:25
08:25
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WN654
WN290
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08:35
08:35
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WN2157
WN290
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09:15
09:15
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WN3076
WN290
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10:30
10:30
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WN2968
WN1152
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10:50
WN2968
WN1110
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11:10
11:10
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WN241
WN3439
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11:45
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WN1543
WN1563
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11:50
WN3043
WN1604
13:25
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WN4666
WN1563
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13:40
13:40
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14:00
WN2970
WN1563
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13:45
13:45
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WN3044
WN1615
14:55
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SHOW RETURN SCHEDULE
CHECK PRICES FOR OAK - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Burbank with Southwest Airlines

  • Total flight time: 5h 40m - 9h 25m.
  • Low-cost airline
  • Oakland and Chicago are both Southwest Airlines focus cities.
  • 26 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
OAK
 
Via BUR
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
SHOW RETURN SCHEDULE
CHECK PRICES FOR OAK - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

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.
  • 258 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
OAK
 
Via LAS
 
MDW
 
Flight
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Aug 3
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Aug 4
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Aug 5
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Aug 6
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Aug 7
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Aug 8
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Aug 9
WN2325
WN2271
05:00
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WN1160
WN1231
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05:05
05:05
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WN2973
WN409
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05:10
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WN2973
WN3130
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05:30
05:30
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WN159
WN3503
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06:05
WN159
WN1231
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06:05
06:05
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WN3503
WN2808
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07:00
WN4348
WN1276
07:35
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WN2044
WN206
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07:50
07:50
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WN4290
WN670
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08:00
08:00
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WN2374
WN4506
09:00
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WN2157
WN3982
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09:15
09:15
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WN4289
WN1423
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09:30
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WN383
WN670
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09:30
09:30
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WN5053
WN2273
10:20
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WN686
WN556
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10:25
10:25
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WN3771
WN2206
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11:20
11:20
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WN1640
WN2766
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11:40
11:40
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WN1911
WN2766
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11:50
WN3040
WN2766
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12:05
WN2205
WN2274
12:15
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WN818
WN2766
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13:00
WN4199
WN3200
14:05
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WN4289
WN2211
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14:30
14:30
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WN364
WN202
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14:30
WN498
WN202
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16:05
WN4539
WN3200
16:45
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WN4291
WN2212
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19:45
19:45
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20:15
WN5072
WN2276
20:15
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WN2499
WN2212
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20:25
20:25
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WN4503
WN2276
21:05
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WN3037
WN2212
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21:55
SHOW RETURN SCHEDULE
CHECK PRICES FOR OAK - MDW

The timetable & schedule information was updated at 2026-04-21

Southwest Airlines

Via Ontario with Southwest Airlines

  • Total flight time: 5h 45m - 7h 50m.
  • 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 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
OAK
 
Via ONT
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN1911
WN2638
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11:50
WN2835
WN3082
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19:55
19:55
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WN1781
WN3082
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21:45
SHOW RETURN SCHEDULE
CHECK PRICES FOR OAK - MDW

The timetable & schedule information was updated at 2026-04-21

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