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.
  • 15 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
OAK
Direct
MDW
 
Flight
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Jun 15
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Jun 16
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WN2211
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05:05
WN2744
05:10
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05:10
05:10
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WN2761
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05:55
05:55
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WN3059
23:55
23:55
23:55
23:55
23:55
23:55
23:55
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
OAK
 
Via DEN
 
MDW
 
Flight
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Jun 15
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Jun 21
WN3397
WN1601
05:05
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05:05
05:05
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WN3041
WN755
05:45
06:00
06:00
05:45
05:45
05:45
05:45
WN3397
WN1603
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06:00
WN3042
WN1601
08:20
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08:20
08:20
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WN3042
WN1524
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08:25
WN3042
WN1603
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09:00
09:00
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08:55
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WN3062
WN1604
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10:00
WN1049
WN1614
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11:30
11:30
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WN2519
WN223
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11:45
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WN1896
WN1614
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12:20
12:20
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WN3043
WN1604
13:25
12:35
12:35
13:25
13:25
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13:05
WN2392
WN1614
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12:40
WN322
WN1614
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12:50
WN3043
WN223
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14:15
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WN3044
WN1614
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14:35
14:35
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14:55
WN3044
WN1615
14:55
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14:55
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
OAK
 
Via BUR
 
MDW
 
Flight
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Jun 15
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Jun 16
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Jun 18
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Jun 19
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Jun 20
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Jun 21
WN2923
WN3156
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06:20
06:20
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WN1855
WN1101
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10:00
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
OAK
 
Via LAS
 
MDW
 
Flight
Mon
Jun 15
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Jun 16
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Jun 18
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Jun 19
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Jun 20
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Jun 21
WN2325
WN2271
05:00
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05:00
05:00
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05:20
WN2938
WN1535
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05:30
05:30
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WN4348
WN162
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06:35
WN4348
WN1651
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07:35
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WN4348
WN1276
07:35
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07:35
07:35
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WN2374
WN2273
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08:00
08:00
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WN2311
WN4249
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08:50
WN2374
WN4506
09:00
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09:00
09:00
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WN2450
WN1782
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09:10
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WN5053
WN2273
10:20
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10:20
10:20
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WN1268
WN1782
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10:25
WN2205
WN2274
12:15
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12:15
12:15
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WN57
WN4143
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12:20
WN2205
WN997
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12:30
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WN4693
WN2812
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13:10
13:10
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WN3308
WN2273
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13:40
WN4199
WN3200
14:05
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14:05
14:05
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WN4539
WN3200
16:45
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16:45
16:45
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WN4503
WN2276
21:05
19:55
19:55
21:05
21:05
20:35
20:45
WN5072
WN2276
20:15
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20:15
20:15
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WN4952
WN2276
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21:00
21:00
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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 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
OAK
 
Via ONT
 
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
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Jun 17
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Jun 18
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Jun 19
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Jun 20
Sun
Jun 21
WN449
WN3153
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20:45
20:45
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----
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SHOW RETURN SCHEDULE
CHECK PRICES FOR OAK - 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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