Airlines with flights from Chicago to Oakland

Southwest is the only airline with non-stop flights from Midway International Airport to Metropolitan Oakland International and the flight time is 4 hours and 40 minutes.

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Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 4 hours and 40 minutes
  • Low-cost airline
  • Chicago and Oakland are both Southwest Airlines focus cities.
  • 13 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
Direct
OAK
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN3366
10:10
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WN2779
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10:15
10:15
10:15
10:15
13:55
10:45
WN3461
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20:25
WN1413
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20:35
20:35
20:35
20:35
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WN4042
21:40
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - OAK

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

Southwest Airlines

Via Denver with Southwest Airlines

  • Total flight time: 5h 40m - 11h 15m.
  • Low-cost airline
  • Chicago and Oakland are both Southwest Airlines focus cities.
  • 171 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via DEN
 
OAK
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2989
WN1713
05:15
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WN2717
WN4678
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06:50
06:30
WN2717
WN2934
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06:40
06:40
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WN2765
WN1577
06:45
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WN136
WN1584
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07:55
WN687
WN269
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09:15
WN2717
WN1583
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09:20
09:20
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WN2412
WN269
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09:20
WN2654
WN3563
09:55
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WN271
WN1583
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10:05
10:05
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10:00
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WN3539
WN2045
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10:05
10:05
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WN4571
WN269
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10:10
WN2960
WN3563
11:00
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WN1148
WN2045
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11:10
11:10
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WN2719
WN2045
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12:00
12:00
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WN2719
WN1629
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12:15
12:15
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WN2719
WN269
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12:25
WN4450
WN1843
13:10
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WN1893
WN1843
13:15
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WN2718
WN4686
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13:40
WN2721
WN1629
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14:05
14:05
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WN2718
WN1692
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14:15
14:15
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WN1271
WN168
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14:15
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WN2768
WN1843
14:30
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WN267
WN168
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14:40
WN2769
WN1843
16:15
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WN655
WN3337
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16:25
16:25
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WN2721
WN168
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18:00
18:00
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17:05
16:45
WN163
WN3337
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17:00
17:00
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WN1497
WN1650
18:00
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - OAK

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

Southwest Airlines

Via Las Vegas with Southwest Airlines

  • Total flight time: 6h 00m - 11h 45m.
  • Low-cost airline
  • Chicago and Oakland are both Southwest Airlines focus cities.
  • 235 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via LAS
 
OAK
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2740
WN3410
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05:25
WN1182
WN2336
06:30
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WN2723
WN126
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06:40
06:40
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WN2740
WN1932
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06:50
06:50
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06:55
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WN2741
WN1932
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06:55
WN347
WN322
07:30
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WN2741
WN2222
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08:35
08:35
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WN4079
WN1204
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08:35
08:35
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WN776
WN1932
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08:50
08:50
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WN1793
WN1319
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09:00
WN2794
WN2422
09:10
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WN2825
WN332
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10:00
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WN4874
WN2221
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10:05
10:05
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WN398
WN2221
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10:05
10:05
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WN3086
WN2221
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10:05
10:05
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WN2741
WN4131
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10:10
10:10
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WN1685
WN1204
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10:10
10:10
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WN2668
WN1204
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10:15
WN1731
WN1204
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10:15
WN332
WN1204
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10:15
WN2707
WN1204
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10:15
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WN2099
WN2221
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10:15
10:15
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WN2783
WN1204
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10:15
10:15
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WN2723
WN4862
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10:20
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WN578
WN1204
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10:20
10:20
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WN4874
WN1204
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10:25
WN3086
WN1204
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10:30
10:30
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WN2742
WN4131
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11:10
11:10
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WN4233
WN1204
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12:15
WN351
WN2225
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12:20
WN2795
WN2286
13:40
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WN4233
WN332
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14:05
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WN3523
WN332
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14:10
14:10
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WN4233
WN2225
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16:00
16:00
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WN2742
WN2225
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16:45
16:45
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16:05
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WN2797
WN4270
16:55
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WN3957
WN551
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17:40
WN2844
WN2289
18:25
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - OAK

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

Southwest Airlines

Via Long Beach with Southwest Airlines

  • Total flight time: 6h 05m - 10h 25m.
  • Low-cost airline
  • Chicago and Oakland are both Southwest Airlines focus cities.
  • 23 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via LGB
 
OAK
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN851
WN2965
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10:05
10:05
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WN2800
WN178
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12:20
WN2512
WN2329
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13:50
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - OAK

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

Southwest Airlines

Via Ontario with Southwest Airlines

  • Total flight time: 6h 05m - 9h 35m.
  • Low-cost airline
  • Chicago and Oakland are both Southwest Airlines focus cities.
  • 20 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via ONT
 
OAK
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2846
WN3155
11:45
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WN4113
WN3185
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12:35
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - OAK

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

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Flight data on this page was last updated on 2026-07-13
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