Airlines with flights from Chicago to San Diego

There are three airlines with scheduled flights between MDW and SAN. Southwest is the only airline with non-stop flights from Midway International Airport to San Diego International Airport and the flight time is 4 hours and 20 minutes.

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Choose airline

Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 4 hours and 20 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 31 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
Direct
SAN
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
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Jun 21
WN3103
05:45
06:00
06:00
05:45
05:45
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06:05
WN4648
10:00
10:20
10:20
10:00
10:00
10:15
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WN2570
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10:50
WN2883
14:15
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14:15
14:15
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WN961
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17:40
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WN2884
21:10
21:05
21:05
21:10
21:10
20:40
21:10
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SAN

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

Southwest Airlines

Via Phoenix with Southwest Airlines

  • Total flight time: 5h 25m - 10h 30m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 245 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via PHX
 
SAN
 
Flight
Mon
Jun 15
Tue
Jun 16
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Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN2858
WN1156
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05:15
WN2858
WN3321
05:20
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05:20
05:20
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WN3586
WN2100
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05:25
05:25
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WN117
WN1677
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06:45
06:45
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WN2520
WN3322
07:10
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07:10
07:10
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WN2520
WN3323
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07:25
WN3016
WN2328
08:40
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08:40
08:40
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WN781
WN5063
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----
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09:10
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WN4189
WN3744
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10:00
WN2984
WN897
10:10
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10:10
10:10
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WN4189
WN5063
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10:45
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WN4189
WN897
11:20
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11:20
11:20
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WN670
WN3208
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11:30
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WN1594
WN1202
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11:45
11:45
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WN1230
WN3017
12:15
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12:15
12:15
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WN554
WN3208
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12:15
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WN2984
WN1202
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12:20
12:20
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WN711
WN3324
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13:10
13:10
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WN1531
WN3324
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14:20
WN1249
WN3324
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16:00
16:00
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WN746
WN2475
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16:35
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WN2861
WN2580
16:35
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16:35
16:35
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WN2862
WN1188
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17:35
17:35
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WN2862
WN4052
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18:30
WN2862
WN3426
18:40
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18:40
18:40
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WN2863
WN3426
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18:55
18:55
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SAN

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

Southwest Airlines

Via Kansas City with Southwest Airlines

  • Total flight time: 5h 25m - 10h 20m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 37 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via MCI
 
SAN
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN2810
WN1341
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09:50
WN709
WN3389
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10:25
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WN3572
WN4457
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12:05
12:05
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----
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WN4407
WN4457
14:10
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14:10
14:10
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WN4407
WN3038
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----
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15:25
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WN2812
WN4457
16:05
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----
16:05
16:05
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SAN

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

Southwest Airlines

Via Denver with Southwest Airlines

  • Total flight time: 5h 40m - 10h 10m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 188 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via DEN
 
SAN
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN2989
WN1699
05:15
05:15
05:15
05:25
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WN2989
WN1653
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05:25
WN2989
WN2689
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05:30
05:30
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WN2765
WN1700
06:45
07:00
07:00
06:45
06:45
07:20
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WN1267
WN3503
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08:00
WN1866
WN3503
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08:50
WN206
WN3503
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09:55
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WN2654
WN3503
09:55
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09:55
09:55
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WN2733
WN3503
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10:10
WN2960
WN1297
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11:20
11:20
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WN2960
WN2665
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11:45
WN1331
WN4160
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12:50
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WN4450
WN1703
13:10
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13:10
13:10
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WN1893
WN1703
13:15
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13:15
13:15
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WN2768
WN2665
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13:25
WN2142
WN1703
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13:45
WN2768
WN4160
14:30
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14:30
14:30
14:15
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WN2766
WN1646
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14:45
14:45
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WN2769
WN1703
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16:40
16:40
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16:50
15:25
WN4450
WN1704
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15:30
WN1893
WN1704
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16:35
WN2844
WN1704
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17:10
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WN481
WN1704
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17:20
WN2675
WN1703
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18:00
18:00
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WN1497
WN1704
18:00
----
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18:00
18:00
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SAN

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

Southwest Airlines

Via Las Vegas with Southwest Airlines

  • Total flight time: 5h 45m - 11h 30m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 225 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via LAS
 
SAN
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN519
WN544
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05:00
WN1182
WN347
06:30
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06:30
06:30
05:10
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WN1182
WN1269
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06:20
06:20
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----
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WN1182
WN1204
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06:30
WN347
WN2272
07:30
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07:30
07:30
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WN2464
WN914
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08:00
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WN347
WN16
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08:00
08:00
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WN2794
WN2272
09:10
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09:10
09:10
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WN296
WN2104
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10:00
WN2104
WN3620
10:00
10:00
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WN1321
WN3620
10:00
10:30
10:30
10:00
10:00
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WN2809
WN1057
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----
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10:00
WN314
WN3620
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10:00
10:00
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WN2104
WN1771
10:00
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10:00
10:00
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WN1771
WN2104
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10:05
WN714
WN1057
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10:05
WN2794
WN2328
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10:10
10:10
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WN1771
WN3620
10:10
10:10
10:10
10:10
10:10
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WN2794
WN2104
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10:15
WN1536
WN1096
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10:15
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WN2794
WN1096
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11:20
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WN2350
WN1288
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12:20
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WN2221
WN2330
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13:20
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WN2795
WN1288
13:40
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13:40
13:40
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WN2795
WN954
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14:55
14:55
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WN1951
WN294
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----
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15:25
WN2795
WN2330
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----
----
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16:10
WN2797
WN1227
16:55
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16:55
16:55
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WN2797
WN1168
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17:10
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WN2797
WN3838
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17:25
17:25
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WN3345
WN294
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17:35
WN2844
WN2331
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17:50
17:50
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WN2844
WN2871
18:25
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----
18:25
18:25
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WN2701
WN2331
----
18:40
18:40
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SAN

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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