Airlines with flights from San Jose to Chicago

There are two airlines with scheduled flights between SJC and MDW. Southwest is the only airline with non-stop flights from Norman Y Mineta San Jose International to Midway International Airport and the flight time is 4 hours and 5 minutes.

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Choose airline

Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 4 hours and 5 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 16 flights per week
  • Boeing 737MAX 8 Passenger
SJC
Direct
MDW
 
Flight
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Jun 15
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Jun 16
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WN4357
10:05
11:15
11:15
10:05
10:05
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11:50
WN2812
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10:30
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WN623
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22:55
WN3886
22:55
22:55
22:55
22:55
22:55
22:55
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SHOW RETURN SCHEDULE
CHECK PRICES FOR SJC - MDW

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

Southwest Airlines

Via Denver with Southwest Airlines

  • Total flight time: 5h 30m - 10h 25m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 145 flights per week
  • Boeing 737MAX 8 Passenger
SJC
 
Via DEN
 
MDW
 
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Jun 15
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WN3693
WN1603
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06:05
06:05
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06:00
WN3526
WN755
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06:00
06:00
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WN3869
WN1524
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06:10
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WN3573
WN1601
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06:15
WN407
WN1603
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06:30
WN3397
WN1603
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06:45
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WN735
WN1524
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08:10
08:10
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WN3666
WN1603
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09:05
WN2354
WN1603
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09:10
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WN3666
WN1251
10:25
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10:25
10:25
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WN1266
WN223
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11:30
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WN1880
WN1614
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12:20
WN3667
WN1604
13:10
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13:10
13:10
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WN1337
WN223
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14:05
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WN2859
WN1614
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14:20
14:20
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WN3668
WN1615
14:35
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14:35
14:35
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WN3668
WN1614
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14:55
SHOW RETURN SCHEDULE
CHECK PRICES FOR SJC - MDW

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

Southwest Airlines

Via Ontario with Southwest Airlines

  • Total flight time: 5h 35m - 8h 10m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 18 flights per week
  • Boeing 737MAX 8 Passenger
SJC
 
Via ONT
 
MDW
 
Flight
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Jun 15
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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
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Jun 21
WN3692
WN3153
20:10
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20:10
20:10
20:40
21:55
WN457
WN3153
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20:55
20:55
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SHOW RETURN SCHEDULE
CHECK PRICES FOR SJC - MDW

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

Southwest Airlines

Via Las Vegas with Southwest Airlines

  • Total flight time: 5h 40m - 10h 35m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 292 flights per week
  • Boeing 737MAX 8 Passenger
SJC
 
Via LAS
 
MDW
 
Flight
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Jun 15
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WN2280
WN496
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06:00
06:00
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WN2280
WN2271
06:00
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06:00
06:00
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WN2192
WN1651
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06:25
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WN2830
WN162
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06:35
WN4933
WN2273
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06:45
06:45
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WN1277
WN1276
07:40
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07:40
07:40
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WN868
WN2273
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07:45
07:45
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WN1204
WN162
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07:50
WN3708
WN2273
08:25
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08:25
08:25
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WN2298
WN4249
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08:55
WN2369
WN2273
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08:55
08:55
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WN2369
WN4506
09:10
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09:10
09:10
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WN2178
WN1782
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09:55
WN2311
WN2273
10:20
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10:20
10:20
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WN3151
WN2274
10:50
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10:50
10:50
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WN205
WN2812
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11:25
11:25
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WN3341
WN2274
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12:50
WN714
WN4143
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13:05
WN2305
WN2274
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13:05
WN4783
WN2812
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13:15
13:15
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WN2039
WN997
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13:30
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WN714
WN2274
13:40
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13:40
13:40
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WN3543
WN2274
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15:15
WN2339
WN3200
15:30
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15:30
15:30
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WN1162
WN3200
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16:10
WN2266
WN3200
17:00
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17:00
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WN1863
WN3200
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17:05
WN2335
WN2276
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19:30
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WN5066
WN2276
19:35
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19:35
19:35
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WN3675
WN2276
20:20
19:50
19:50
20:20
20:20
20:45
21:25
WN3676
WN2276
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20:55
20:55
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SHOW RETURN SCHEDULE
CHECK PRICES FOR SJC - MDW

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

Southwest Airlines

Via Phoenix with Southwest Airlines

  • Total flight time: 5h 40m - 9h 50m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 161 flights per week
  • Boeing 737MAX 8 Passenger
SJC
 
Via PHX
 
MDW
 
Flight
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Jun 15
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Jun 16
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Jun 17
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Jun 21
WN3186
WN1677
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06:00
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WN3232
WN284
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06:05
WN1855
WN554
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06:10
06:10
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WN3186
WN4066
06:25
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06:25
06:25
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WN3708
WN4418
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08:00
WN2154
WN2340
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09:05
WN2311
WN3297
10:20
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10:20
10:20
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WN765
WN3297
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11:15
11:15
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WN3232
WN3297
11:40
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11:40
11:40
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WN3525
WN3190
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13:00
13:00
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WN1230
WN3297
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13:30
13:30
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WN714
WN2521
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14:15
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WN3266
WN2521
16:05
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16:05
16:05
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WN3526
WN3298
17:45
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17:45
17:45
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WN3696
WN3298
19:00
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19:00
19:00
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19:30
WN3112
WN3298
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19:45
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WN3697
WN3298
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21:10
21:10
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SHOW RETURN SCHEDULE
CHECK PRICES FOR SJC - 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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