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 35 minutes.

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Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 4 hours and 35 minutes
  • Low-cost airline
  • Chicago and Oakland are both Southwest Airlines focus cities.
  • 15 flights per week
  • Boeing 737MAX 8 Passenger
MDW
Direct
OAK
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
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Jun 18
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Jun 19
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Jun 20
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Jun 21
WN3366
10:10
10:00
10:00
10:10
10:10
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10:00
WN2221
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13:20
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WN2710
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21:00
21:00
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WN4042
21:40
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21:40
21:40
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21:25
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
MDW
 
Via DEN
 
OAK
 
Flight
Mon
Jun 15
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Jun 16
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Jun 17
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Jun 18
Fri
Jun 19
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Jun 20
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Jun 21
WN2989
WN1713
05:15
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05:15
05:15
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05:25
WN2989
WN1240
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05:30
05:30
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05:25
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WN2765
WN1577
06:45
07:00
07:00
06:45
06:45
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WN2765
WN500
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07:20
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WN2654
WN3563
09:55
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09:55
09:55
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WN2733
WN4977
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10:10
WN2960
WN3563
11:00
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11:00
11:00
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WN2960
WN1469
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11:20
11:20
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WN2960
WN4977
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11:45
WN1331
WN247
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12:50
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WN4450
WN1843
13:10
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13:10
13:10
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WN1893
WN1843
13:15
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13:15
13:15
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WN2142
WN1843
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13:45
WN2768
WN247
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14:15
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WN2768
WN1843
14:30
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14:30
14:30
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WN2766
WN1843
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14:45
14:45
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WN2769
WN1843
16:15
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16:15
16:15
16:50
15:25
WN4450
WN1650
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15:30
WN1893
WN1650
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16:35
WN2769
WN2425
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16:40
16:40
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WN2844
WN1650
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17:10
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WN481
WN1685
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17:20
WN2675
WN2425
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18:00
18:00
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WN1497
WN1650
18:00
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18:00
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
MDW
 
Via LAS
 
OAK
 
Flight
Mon
Jun 15
Tue
Jun 16
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Jun 17
Thu
Jun 18
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Jun 19
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Jun 20
Sun
Jun 21
WN519
WN1811
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05:00
WN1182
WN1254
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06:20
06:20
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05:10
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WN1182
WN2336
06:30
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06:30
06:30
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06:30
WN347
WN322
07:30
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07:30
07:30
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WN2464
WN1718
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08:00
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WN347
WN2199
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08:00
08:00
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WN2794
WN2422
09:10
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09:10
09:10
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WN314
WN2286
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10:00
10:00
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WN2809
WN1592
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10:00
WN2104
WN123
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10:00
10:00
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WN296
WN3980
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10:00
WN714
WN2334
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10:05
WN1771
WN3980
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10:05
WN2794
WN2328
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10:10
10:10
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WN1771
WN123
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10:10
10:10
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WN2104
WN3980
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10:10
WN2794
WN170
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10:15
WN1536
WN4488
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10:15
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WN1321
WN2286
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10:30
10:30
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WN2794
WN4488
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11:20
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WN2350
WN2286
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12:20
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WN2795
WN2286
13:40
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13:40
13:40
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WN2795
WN4270
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14:55
14:55
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16:10
WN1951
WN2288
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15:25
WN2797
WN4270
16:55
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16:55
16:55
17:10
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WN2797
WN2288
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17:25
17:25
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WN3345
WN4270
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17:35
WN2844
WN4467
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17:50
17:50
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WN2844
WN2289
18:25
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18:25
18:25
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WN2701
WN4467
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18:40
18:40
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WN1904
WN978
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20:20
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
MDW
 
Via LGB
 
OAK
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN4413
WN2334
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----
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11:10
WN4413
WN4523
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14:40
14:40
----
----
----
----
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
MDW
 
Via ONT
 
OAK
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN2846
WN3155
11:45
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11:45
11:45
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WN3874
WN3155
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----
----
----
----
12:15
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WN2846
WN3082
----
15:50
15:50
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - OAK

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

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