Airlines with flights from Chicago to San Jose

There are two airlines with scheduled flights between MDW and SJC. Southwest is the only airline with non-stop flights from Midway International Airport to Norman Y Mineta San Jose 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 is a Southwest Airlines focus city (Operating base).
  • 18 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
MDW
Direct
SJC
 
Flight
Mon
Jun 15
Tue
Jun 16
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Jun 17
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Jun 18
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Jun 20
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Jun 21
WN3115
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10:05
WN3752
10:05
10:05
10:05
10:05
10:05
10:20
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WN2659
20:50
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20:50
20:50
20:25
21:25
WN1662
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20:55
20:55
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SJC

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

Southwest Airlines

Via Denver with Southwest Airlines

  • Total flight time: 5h 50m - 11h 10m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 178 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
MDW
 
Via DEN
 
SJC
 
Flight
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Jun 15
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Jun 19
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Jun 20
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Jun 21
WN2989
WN494
05:15
05:30
05:30
05:15
05:15
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WN2989
WN439
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05:25
WN2989
WN1568
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05:25
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WN2765
WN2384
06:45
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06:45
06:45
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WN2765
WN397
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07:00
07:00
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WN1267
WN2743
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08:00
WN1866
WN2743
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08:50
WN1102
WN4130
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09:00
09:00
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WN2654
WN2743
09:55
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09:55
09:55
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WN206
WN2743
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09:55
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WN2733
WN2743
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10:10
WN680
WN2743
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10:15
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WN1331
WN290
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12:50
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WN4450
WN1727
13:10
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13:10
13:10
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WN1893
WN1727
13:15
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13:15
13:15
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WN2142
WN1727
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13:45
WN2768
WN290
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14:15
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WN2768
WN1727
14:30
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14:30
14:30
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WN2766
WN1727
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14:45
14:45
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WN2769
WN1727
16:15
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16:15
16:15
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15:25
WN4450
WN1728
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15:30
WN1893
WN1728
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16:35
WN2769
WN1728
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16:40
16:40
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16:50
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WN2844
WN1728
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17:10
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WN481
WN1728
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17:20
WN1497
WN1728
18:00
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18:00
18:00
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WN2675
WN1728
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18:00
18:00
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SJC

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

Southwest Airlines

Via Las Vegas with Southwest Airlines

  • Total flight time: 6h 00m - 11h 40m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 221 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
MDW
 
Via LAS
 
SJC
 
Flight
Mon
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 21
WN519
WN439
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05:00
WN1182
WN713
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05:10
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WN1182
WN919
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06:20
06:20
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WN1182
WN439
06:30
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06:30
06:30
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06:30
WN347
WN1242
07:30
08:00
08:00
07:30
07:30
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WN2464
WN2260
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08:00
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WN2794
WN1242
09:10
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09:10
09:10
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WN296
WN984
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10:00
WN314
WN2350
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10:00
10:00
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WN2104
WN2350
10:00
10:00
10:00
10:00
10:00
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WN1321
WN2350
10:00
10:30
10:30
10:00
10:00
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WN2809
WN1321
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10:00
WN1771
WN984
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10:05
WN2104
WN984
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10:10
WN1771
WN2350
10:10
10:10
10:10
10:10
10:10
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WN2794
WN3845
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10:15
WN2794
WN4275
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11:20
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WN2350
WN166
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12:20
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WN2221
WN2352
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13:20
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WN2795
WN342
13:40
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13:40
13:40
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WN2795
WN3865
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14:55
14:55
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16:10
WN1951
WN2350
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15:25
WN2797
WN3865
16:55
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16:55
16:55
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WN2797
WN2352
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17:25
17:25
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17:10
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WN3345
WN2352
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17:35
WN2844
WN660
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17:50
17:50
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WN2701
WN660
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18:40
18:40
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SJC

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

Southwest Airlines

Via San Diego with Southwest Airlines

  • Total flight time: 6h 05m - 11h 25m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 91 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
MDW
 
Via SAN
 
SJC
 
Flight
Mon
Jun 15
Tue
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
WN3103
WN4509
05:45
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05:45
05:45
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06:05
WN3103
WN2100
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06:00
06:00
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WN347
WN1181
07:30
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07:30
07:30
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WN4648
WN3538
10:00
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10:00
10:00
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WN2809
WN3540
10:05
10:15
10:15
10:05
10:05
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WN4905
WN3820
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10:15
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WN4648
WN3820
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10:15
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WN4648
WN3539
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10:20
10:20
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WN2570
WN3539
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10:50
WN1139
WN3540
11:00
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11:00
11:00
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WN2876
WN3823
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12:30
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WN2883
WN3541
14:15
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14:15
14:15
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SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SJC

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

Southwest Airlines

Via Los Angeles with Southwest Airlines

  • Total flight time: 6h 05m - 9h 25m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 55 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
MDW
 
Via LAX
 
SJC
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN4637
WN2431
05:10
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05:10
05:10
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WN3014
WN2431
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05:35
05:35
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WN2433
WN1570
10:10
10:10
10:10
10:10
10:10
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WN188
WN2434
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15:05
15:05
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WN188
WN3222
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18:30
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SJC

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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