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 40 minutes.

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Choose airline

Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 4 hours and 40 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 14 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
Direct
SJC
 
Flight
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Aug 3
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WN3752
10:05
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WN2756
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10:10
WN2830
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10:15
10:15
13:15
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WN3502
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10:20
10:20
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WN3810
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20:30
20:30
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18:25
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WN4996
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20:40
WN576
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20:50
20:50
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WN2659
20:50
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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 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via DEN
 
SJC
 
Flight
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WN494
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WN2765
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WN199
WN1676
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WN314
WN1676
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WN687
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09:15
WN2412
WN4499
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WN1536
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WN2654
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WN271
WN1500
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WN271
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WN2718
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WN1148
WN4744
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WN2719
WN4744
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WN2719
WN4499
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WN4450
WN1727
13:10
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WN1893
WN1727
13:15
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WN2718
WN427
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13:40
WN2721
WN236
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14:05
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WN1271
WN4675
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WN2718
WN4744
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14:15
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WN2768
WN1727
14:30
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WN2769
WN1727
16:15
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WN655
WN1679
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16:25
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WN2721
WN1679
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18:00
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WN163
WN1679
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17:00
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WN2721
WN4675
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17:05
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WN1497
WN1728
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 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via LAS
 
SJC
 
Flight
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Aug 3
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WN2740
WN4761
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WN1182
WN439
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WN2723
WN843
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WN2740
WN1682
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WN1063
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WN347
WN1242
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WN4079
WN2293
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08:35
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WN2741
WN955
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08:35
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WN776
WN840
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08:50
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WN1793
WN372
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09:00
WN2794
WN1242
09:10
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WN2104
WN2350
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WN1321
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WN4618
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WN4874
WN2290
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10:05
10:05
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WN3086
WN2290
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10:05
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WN1685
WN2293
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10:10
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WN2741
WN2290
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WN1771
WN2350
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WN1731
WN2293
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WN332
WN2293
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WN578
WN372
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10:20
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WN4874
WN2293
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10:25
WN3086
WN2293
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10:30
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WN2742
WN2290
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11:10
11:10
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WN4233
WN2293
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12:15
WN351
WN2118
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WN2795
WN342
13:40
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WN4233
WN843
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WN3874
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16:00
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WN2742
WN2294
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16:45
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WN2797
WN3865
16:55
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WN3957
WN2296
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17:40
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 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via SAN
 
SJC
 
Flight
Mon
Aug 3
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WN3103
WN4509
05:45
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WN2815
WN1667
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06:10
WN2814
WN755
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06:15
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WN347
WN1181
07:30
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WN2814
WN480
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WN4648
WN3538
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WN2814
WN3462
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10:05
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WN2809
WN3540
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WN2815
WN2205
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10:15
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WN2814
WN4465
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WN1139
WN3540
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WN534
WN3527
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WN298
WN4137
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WN363
WN3527
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WN2883
WN3541
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WN518
WN1430
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14:50
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WN2816
WN818
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15:05
15:05
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WN1356
WN4137
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15:10
15:10
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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 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
MDW
 
Via LAX
 
SJC
 
Flight
Mon
Aug 3
Tue
Aug 4
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WN4637
WN2431
05:10
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WN1104
WN1758
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06:00
WN1748
WN1532
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07:00
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WN188
WN2449
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09:25
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WN4164
WN2449
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10:05
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WN2433
WN1570
10:10
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WN3343
WN2684
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10:10
10:10
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WN4772
WN2684
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10:10
WN865
WN2449
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10:15
10:15
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WN2723
WN2449
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10:20
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WN4772
WN2449
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12:20
12:20
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WN2327
WN596
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13:50
13:50
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WN997
WN1316
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17:15
17:15
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WN4683
WN2380
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17:20
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - SJC

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

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