Southwest Airlines flights from San Jose (SJC) to Chicago O'Hare (ORD).

Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:
Sun 15:00 San Jose (SJC) B 22:55 Chicago O'Hare (ORD) 5
Southwest Airlines WN 2953 1-stop Boeing 737 MAX 8 (7M8) 5:55 Effective 2026-04-12 through 2026-05-17
Sun 15:00 San Jose (SJC) B 22:55 Chicago O'Hare (ORD) 5
Southwest Airlines WN 2953 1-stop Boeing 737 MAX 8 (7M8) 5:55 Operates only on 2026-05-31
Sun 14:20 San Jose (SJC) B 23:55 Chicago O'Hare (ORD) 5
Southwest Airlines WN 882 2-stop Boeing 737 MAX 8 (7M8) 7:35 Operates only on 2026-05-24
Sun 13:05 San Jose (SJC) B 22:55 Chicago O'Hare (ORD) 5
Southwest Airlines WN 2305 2-stop Boeing 737 MAX 8 (7M8) 7:50 Effective 2026-06-07 through 2026-08-02


Southwest Airlines flights from San Jose (SJC) to Chicago O'Hare (ORD).
Select flight date:
FLIGHT SCHEDULE
Non-Direct Flights:

Effective 2026-04-12 through 2026-05-17
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:55, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Operates only on 2026-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 5:55, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Operates only on 2026-05-24
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 7:35, 2-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Effective 2026-06-07 through 2026-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 7:50, 2-stop
Boeing 737 MAX 8 (7M8)
  • A domestic route departing from the San Jose airport (SJC) and arriving at Chicago O'Hare airport (ORD).
  • The flight distance is 1824 miles, or 2935 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.