All airlines flying from San Jose (SJC) to Midway, Chicago (MDW).

Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:
Sat 07:20 San Jose (SJC) B 15:15 Midway, Chicago (MDW)
Southwest Airlines WN 106 1-stop Boeing 737-700 (73W) 5:55 Effective 2025-01-11 through 2025-02-08
Mon,Thu,Fri 06:30 San Jose (SJC) B 15:00 Midway, Chicago (MDW)
Southwest Airlines WN 967 1-stop Boeing 737 MAX 8 (7M8) 6:30 Valid until 2024-09-30
Sun 16:45 San Jose (SJC) B 00:50 Midway, Chicago (MDW)
Southwest Airlines WN 1376 1-stop Boeing 737-800 (73H) 6:05 Operates only on 2024-12-01
The flight arrives 1 day after departure.
Mon,Thu,Fri 15:30 San Jose (SJC) B 23:35 Midway, Chicago (MDW)
Southwest Airlines WN 1498 1-stop Boeing 737-700 (73W) 6:05 Valid until 2024-09-30
Sat 12:25 San Jose (SJC) B 20:35 Midway, Chicago (MDW)
Southwest Airlines WN 1584 1-stop Boeing 737-700 (73W) 6:10 Effective 2024-10-05 through 2024-11-02
Sun 07:50 San Jose (SJC) B 15:40 Midway, Chicago (MDW)
Southwest Airlines WN 1933 1-stop Boeing 737-800 (73H) 5:50 Operates only on 2024-12-01
Sun 08:35 San Jose (SJC) B 17:00 Midway, Chicago (MDW)
Southwest Airlines WN 1944 1-stop Boeing 737 MAX 8 (7M8) 6:25 Operates only on 2024-09-01
Tue,Wed 07:45 San Jose (SJC) B 16:45 Midway, Chicago (MDW)
Southwest Airlines WN 2113 1-stop Boeing 737 MAX 8 (7M8) 7:00 Valid until 2024-10-02
Thu,Fri,Sun 08:40 San Jose (SJC) B 17:35 Midway, Chicago (MDW)
Southwest Airlines WN 2299 1-stop Boeing 737-700 (73W) 6:55 Effective 2025-01-12 through 2025-01-17
Mon,Sun 08:40 San Jose (SJC) B 17:35 Midway, Chicago (MDW)
Southwest Airlines WN 2299 1-stop Boeing 737-700 (73W) 6:55 Effective 2025-01-20 through 2025-01-26
Thu,Fri,Sun 08:40 San Jose (SJC) B 17:35 Midway, Chicago (MDW)
Southwest Airlines WN 2299 1-stop Boeing 737-700 (73W) 6:55 Effective 2025-02-02 through 2025-02-07
Mon 08:40 San Jose (SJC) B 17:35 Midway, Chicago (MDW)
Southwest Airlines WN 2299 1-stop Boeing 737-700 (73W) 6:55 Operates only on 2025-02-10
Mon,Tue,Thu 08:40 San Jose (SJC) B 17:35 Midway, Chicago (MDW)
Southwest Airlines WN 2299 1-stop Boeing 737-700 (73W) 6:55 Effective 2025-02-18 through 2025-02-24
Mon 08:40 San Jose (SJC) B 17:35 Midway, Chicago (MDW)
Southwest Airlines WN 2299 1-stop Boeing 737-700 (73W) 6:55 Operates only on 2025-03-03
Tue,Wed 11:45 San Jose (SJC) B 19:40 Midway, Chicago (MDW)
Southwest Airlines WN 2728 1-stop Boeing 737-700 (73W) 5:55 Valid until 2024-10-02
Sun 15:30 San Jose (SJC) B 23:15 Midway, Chicago (MDW)
Southwest Airlines WN 2817 1-stop Boeing 737-700 (73W) 5:45 Effective 2024-09-08 through 2024-09-29
Sun 14:40 San Jose (SJC) B 22:50 Midway, Chicago (MDW)
Southwest Airlines WN 2860 1-stop Boeing 737-700 (73W) 6:10 Operates only on 2024-09-01
Sun 11:45 San Jose (SJC) B 19:15 Midway, Chicago (MDW)
Southwest Airlines WN 2912 1-stop Boeing 737-700 (73W) 5:30 Operates only on 2024-12-01
Tue,Wed 08:05 San Jose (SJC) B 16:35 Midway, Chicago (MDW)
Southwest Airlines WN 2995 1-stop Boeing 737 MAX 8 (7M8) 6:30 Valid until 2024-10-02
Thu 09:05 San Jose (SJC) B 17:10 Midway, Chicago (MDW)
Southwest Airlines WN 3002 1-stop Boeing 737-700 (73W) 6:05 Operates only on 2024-11-28
Sun 07:50 San Jose (SJC) B 16:45 Midway, Chicago (MDW)
Southwest Airlines WN 3069 1-stop Boeing 737-700 (73W) 6:55 Operates only on 2024-09-01
Mon,Thu,Fri 10:35 San Jose (SJC) B 19:00 Midway, Chicago (MDW)
Southwest Airlines WN 3191 1-stop Boeing 737 MAX 8 (7M8) 6:25 Effective 2024-10-03 through 2024-10-28
Fri 10:35 San Jose (SJC) B 19:00 Midway, Chicago (MDW)
Southwest Airlines WN 3191 1-stop Boeing 737 MAX 8 (7M8) 6:25 Operates only on 2024-11-01
Tue,Wed 14:45 San Jose (SJC) B 22:45 Midway, Chicago (MDW)
Southwest Airlines WN 3883 1-stop Boeing 737-700 (73W) 6:00 Effective 2024-10-08 through 2024-10-30
Mon,Thu,Fri 14:25 San Jose (SJC) B 21:55 Midway, Chicago (MDW)
Southwest Airlines WN 4132 1-stop Boeing 737-700 (73W) 5:30 Effective 2024-10-03 through 2024-10-28
Fri 14:25 San Jose (SJC) B 21:55 Midway, Chicago (MDW)
Southwest Airlines WN 4132 1-stop Boeing 737-700 (73W) 5:30 Operates only on 2024-11-01
Mon,Thu,Fri 08:30 San Jose (SJC) B 18:00 Midway, Chicago (MDW)
Southwest Airlines WN 597 2-stop Boeing 737-700 (73W) 7:30 Valid until 2024-09-30
Sat 12:55 San Jose (SJC) B 22:25 Midway, Chicago (MDW)
Southwest Airlines WN 1049 2-stop Boeing 737-700 (73W) 7:30 Effective 2025-02-15 through 2025-03-01
Mon-Wed 12:10 San Jose (SJC) B 22:05 Midway, Chicago (MDW)
Southwest Airlines WN 1389 2-stop Boeing 737-700 (73W) 7:55 Effective 2024-11-26 through 2024-12-02
Mon,Thu,Fri,Sun 12:10 San Jose (SJC) B 22:05 Midway, Chicago (MDW)
Southwest Airlines WN 1389 2-stop Boeing 737-700 (73W) 7:55 Effective 2024-12-20 through 2025-01-02
Sun 12:10 San Jose (SJC) B 22:05 Midway, Chicago (MDW)
Southwest Airlines WN 1389 2-stop Boeing 737-700 (73W) 7:55 Operates only on 2025-01-05
Mon,Thu,Fri 15:55 San Jose (SJC) B 01:20 Midway, Chicago (MDW)
Southwest Airlines WN 1763 2-stop Boeing 737-700 (73W) 7:25 Effective 2024-10-03 through 2024-10-28
The flight arrives 1 day after departure.
Fri 15:55 San Jose (SJC) B 01:20 Midway, Chicago (MDW)
Southwest Airlines WN 1763 2-stop Boeing 737-700 (73W) 7:25 Operates only on 2024-11-01
The flight arrives 1 day after departure.
Mon,Thu,Fri 08:15 San Jose (SJC) B 17:35 Midway, Chicago (MDW)
Southwest Airlines WN 1781 2-stop Boeing 737-700 (73W) 7:20 Effective 2024-10-03 through 2024-10-28
Fri 08:15 San Jose (SJC) B 17:35 Midway, Chicago (MDW)
Southwest Airlines WN 1781 2-stop Boeing 737-700 (73W) 7:20 Operates only on 2024-11-01
Mon,Thu,Fri 07:50 San Jose (SJC) B 16:50 Midway, Chicago (MDW)
Southwest Airlines WN 2462 2-stop Boeing 737-700 (73W) 7:00 Valid until 2024-09-30
Thu,Fri,Sun 09:30 San Jose (SJC) B 18:55 Midway, Chicago (MDW)
Southwest Airlines WN 2756 2-stop Boeing 737-700 (73W) 7:25 Effective 2024-11-03 through 2024-11-10
Mon,Thu,Fri,Sun 09:30 San Jose (SJC) B 18:55 Midway, Chicago (MDW)
Southwest Airlines WN 2756 2-stop Boeing 737-700 (73W) 7:25 Effective 2024-11-11 through 2024-11-25
Fri,Sun 09:30 San Jose (SJC) B 18:55 Midway, Chicago (MDW)
Southwest Airlines WN 2756 2-stop Boeing 737-700 (73W) 7:25 Effective 2024-12-08 through 2024-12-15
Thu 09:30 San Jose (SJC) B 18:55 Midway, Chicago (MDW)
Southwest Airlines WN 2756 2-stop Boeing 737-700 (73W) 7:25 Operates only on 2024-12-19
Fri 09:30 San Jose (SJC) B 18:55 Midway, Chicago (MDW)
Southwest Airlines WN 2756 2-stop Boeing 737-700 (73W) 7:25 Operates only on 2025-01-03
Sun 14:50 San Jose (SJC) B 00:25 Midway, Chicago (MDW)
Southwest Airlines WN 4569 2-stop Boeing 737-700 (73W) 7:35 Effective 2024-10-06 through 2024-10-27
The flight arrives 1 day after departure.
Mon,Thu,Fri,Sun 07:55 San Jose (SJC) B 19:25 Midway, Chicago (MDW)
Southwest Airlines WN 805 3-stop Boeing 737-700 (73W) 9:30 Effective 2025-02-13 through 2025-02-17
Thu,Fri,Sun 07:55 San Jose (SJC) B 19:25 Midway, Chicago (MDW)
Southwest Airlines WN 805 3-stop Boeing 737-700 (73W) 9:30 Effective 2025-02-21 through 2025-03-02
Mon,Thu,Fri 10:05 San Jose (SJC) B 21:15 Midway, Chicago (MDW)
Southwest Airlines WN 2375 3-stop Boeing 737-700 (73W) 9:10 Effective 2024-10-03 through 2024-10-28
Fri 10:05 San Jose (SJC) B 21:15 Midway, Chicago (MDW)
Southwest Airlines WN 2375 3-stop Boeing 737-700 (73W) 9:10 Operates only on 2024-11-01
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All airlines flying from San Jose (SJC) to Midway, Chicago (MDW).
Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:

Effective 2025-01-11 through 2025-02-08
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 5:55, 1-stop
Boeing 737-700 (73W)

Valid until 2024-09-30
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 6:30, 1-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2024-12-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 6:05, 1-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Valid until 2024-09-30
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 6:05, 1-stop
Boeing 737-700 (73W)

Effective 2024-10-05 through 2024-11-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 6:10, 1-stop
Boeing 737-700 (73W)

Operates only on 2024-12-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:50, 1-stop
Boeing 737-800 (73H)

Operates only on 2024-09-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 6:25, 1-stop
Boeing 737 MAX 8 (7M8)

Valid until 2024-10-02
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 7:00, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-01-12 through 2025-01-17
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 6:55, 1-stop
Boeing 737-700 (73W)

Effective 2025-01-20 through 2025-01-26
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 6:55, 1-stop
Boeing 737-700 (73W)

Effective 2025-02-02 through 2025-02-07
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 6:55, 1-stop
Boeing 737-700 (73W)

Operates only on 2025-02-10
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 6:55, 1-stop
Boeing 737-700 (73W)

Effective 2025-02-18 through 2025-02-24
Mon
Tue
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 6:55, 1-stop
Boeing 737-700 (73W)

Operates only on 2025-03-03
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 6:55, 1-stop
Boeing 737-700 (73W)

Valid until 2024-10-02
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 5:55, 1-stop
Boeing 737-700 (73W)

Effective 2024-09-08 through 2024-09-29
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:45, 1-stop
Boeing 737-700 (73W)

Operates only on 2024-09-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 6:10, 1-stop
Boeing 737-700 (73W)

Operates only on 2024-12-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:30, 1-stop
Boeing 737-700 (73W)

Valid until 2024-10-02
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 6:30, 1-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2024-11-28
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 6:05, 1-stop
Boeing 737-700 (73W)

Operates only on 2024-09-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 6:55, 1-stop
Boeing 737-700 (73W)

Effective 2024-10-03 through 2024-10-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 6:25, 1-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2024-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 6:25, 1-stop
Boeing 737 MAX 8 (7M8)

Effective 2024-10-08 through 2024-10-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 6:00, 1-stop
Boeing 737-700 (73W)

Effective 2024-10-03 through 2024-10-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 5:30, 1-stop
Boeing 737-700 (73W)

Operates only on 2024-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 5:30, 1-stop
Boeing 737-700 (73W)

Valid until 2024-09-30
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 7:30, 2-stop
Boeing 737-700 (73W)

Effective 2025-02-15 through 2025-03-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 7:30, 2-stop
Boeing 737-700 (73W)

Effective 2024-11-26 through 2024-12-02
Mon
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 7:55, 2-stop
Boeing 737-700 (73W)

Effective 2024-12-20 through 2025-01-02
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 7:55, 2-stop
Boeing 737-700 (73W)

Operates only on 2025-01-05
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 7:55, 2-stop
Boeing 737-700 (73W)

Effective 2024-10-03 through 2024-10-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 7:25, 2-stop
Boeing 737-700 (73W)
The flight arrives 1 day after departure.

Operates only on 2024-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 7:25, 2-stop
Boeing 737-700 (73W)
The flight arrives 1 day after departure.

Effective 2024-10-03 through 2024-10-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 7:20, 2-stop
Boeing 737-700 (73W)

Operates only on 2024-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 7:20, 2-stop
Boeing 737-700 (73W)

Valid until 2024-09-30
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 7:00, 2-stop
Boeing 737-700 (73W)

Effective 2024-11-03 through 2024-11-10
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 7:25, 2-stop
Boeing 737-700 (73W)

Effective 2024-11-11 through 2024-11-25
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 7:25, 2-stop
Boeing 737-700 (73W)

Effective 2024-12-08 through 2024-12-15
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 7:25, 2-stop
Boeing 737-700 (73W)

Operates only on 2024-12-19
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 7:25, 2-stop
Boeing 737-700 (73W)

Operates only on 2025-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 7:25, 2-stop
Boeing 737-700 (73W)

Effective 2024-10-06 through 2024-10-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 7:35, 2-stop
Boeing 737-700 (73W)
The flight arrives 1 day after departure.

Effective 2025-02-13 through 2025-02-17
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 9:30, 3-stop
Boeing 737-700 (73W)

Effective 2025-02-21 through 2025-03-02
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 9:30, 3-stop
Boeing 737-700 (73W)

Effective 2024-10-03 through 2024-10-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 9:10, 3-stop
Boeing 737-700 (73W)

Operates only on 2024-11-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
-
Duration: 9:10, 3-stop
Boeing 737-700 (73W)
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  • A domestic route departing from the San Jose airport (SJC) and arriving at Midway, Chicago airport (MDW).
  • The flight distance is 1832 miles, or 2948 km.
  • The timezone of the departure airport is UTC-8 , and the timezone of the arrival airport is UTC-6 . Current time at the point of departure is (loading...), and (loading...) at the point of arrival. There is a (loading...) hour time difference between the airports.
  • For direct flights, the flight time varies between 4:05 and 4:15.