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).
  • 14 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
SJC
Direct
MDW
 
Flight
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Aug 3
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Aug 4
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Aug 5
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Aug 9
WN4847
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06:10
WN208
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09:55
09:55
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07:10
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WN4357
10:05
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WN1286
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11:20
11:20
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WN3886
22:55
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WN3607
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23:00
23:00
23:00
23:00
23:00
23:00
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
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
SJC
 
Via DEN
 
MDW
 
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WN1497
WN523
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06:05
06:05
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WN3578
WN4021
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06:10
WN3578
WN1428
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06:45
06:45
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WN3578
WN450
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06:50
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WN1289
WN1561
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07:00
WN1663
WN1561
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07:30
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WN1895
WN295
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08:30
WN1646
WN1428
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08:40
08:40
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WN556
WN1561
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08:55
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WN3666
WN1251
10:25
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WN3579
WN1110
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10:45
10:45
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WN379
WN1563
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11:55
11:55
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WN1063
WN1563
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11:55
WN3580
WN3439
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12:50
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WN3667
WN1604
13:10
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WN3580
WN1563
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13:25
13:25
13:25
13:25
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14:20
WN3668
WN1615
14:35
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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 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
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
SJC
 
Via ONT
 
MDW
 
Flight
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Aug 3
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Aug 9
WN2882
WN2638
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12:10
WN3692
WN3153
20:10
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WN2377
WN3082
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20:10
20:10
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WN2165
WN3082
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21:00
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
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
SJC
 
Via LAS
 
MDW
 
Flight
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Aug 3
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WN2280
WN2271
06:00
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WN2972
WN409
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06:15
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WN1312
WN1231
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06:15
06:15
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WN2972
WN3503
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06:25
WN1277
WN1276
07:40
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WN1538
WN206
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07:55
07:55
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WN3708
WN2273
08:25
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WN4109
WN670
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08:40
08:40
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WN1702
WN3982
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08:45
08:45
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WN2369
WN4506
09:10
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WN1362
WN2206
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09:30
09:30
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WN893
WN556
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09:40
09:40
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WN2884
WN1423
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09:55
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WN2311
WN2273
10:20
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WN1312
WN1423
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10:25
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WN2433
WN2766
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10:30
10:30
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WN3151
WN2274
10:50
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WN1088
WN2766
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10:55
10:55
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WN2288
WN2766
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11:20
WN1702
WN2766
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12:05
12:05
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13:10
WN3182
WN2206
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12:15
12:15
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WN714
WN2274
13:40
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WN3592
WN2211
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15:10
15:10
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WN3590
WN202
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15:20
WN2339
WN3200
15:30
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WN3593
WN202
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16:10
WN2266
WN3200
17:00
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WN626
WN202
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17:00
WN5066
WN2276
19:35
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WN3675
WN2276
20:20
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WN4851
WN2212
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20:30
20:30
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WN749
WN2212
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21:20
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
    Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737-700 Passenger (Scimitar Winglets)
SJC
 
Via PHX
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN3186
WN4066
06:25
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WN900
WN3221
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06:55
06:55
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WN4986
WN3285
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08:00
08:00
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WN3616
WN2012
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09:45
09:45
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WN2745
WN574
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10:15
WN2311
WN3297
10:20
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WN2527
WN4978
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11:35
11:35
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WN3232
WN3297
11:40
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WN1140
WN1129
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11:40
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WN3617
WN657
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12:40
12:40
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WN4577
WN1129
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14:55
WN733
WN1129
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15:20
WN3266
WN2521
16:05
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WN3526
WN3298
17:45
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WN3696
WN3298
19:00
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WN3618
WN3224
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20:20
20:20
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20:15
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 2026-07-21
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