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Direct flights from Chicago to San Jose

Airlines Schedules

MDW - SJC route map All flights from MDW to SJC non-stop. There are direct flights from Chicago Midway International (MDW), Illinois, USA to Norman Y Mineta San Jose International (SJC), California, USA with Southwest Airlines. 14 weekly departures are currently scheduled on this route. Departure times range from 09:35 to 21:20 depending on the schedule period. The flight distance is 1843 miles (2965 km). Flight time ranges from 4 hours and 35 minutes to 4 hours and 50 minutes.

MDW
Chicago Midway
USAChicago , USA
SJC
Norman Y Mineta San Jose
USASan Jose , USA
MDW
Chicago Midway
USAChicago , USA
Norman Y Mineta San Jose
USASan Jose , USA
SJC
Flight time 4h 35min to 4h 50min
Updated Sep 28, 2026
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Airlines with non-stop routes:

Southwest Airlines Low-cost carrier

Departure times vary between 09:35 and 21:20
S
M
T
W
T
F
S
Sun
Mon
Tue
Wed
Thu
Fri
Sat
14 flights/week
14 flights/week
Weekday-labels: HAS FLIGHTS UPCOMING NO FLIGHTS
View all flight dates
Flight schedule from Chicago to San Jose with Southwest Airlines

This is a weekly direct flight schedule for Southwest Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.

 
Flight
Mon
Nov 2
Tue
Nov 3
Wed
Nov 4
Thu
Nov 5
Fri
Nov 6
Sat
Nov 7
Sun
Nov 8
WN3035
10:10
10:10
10:10
10:10
10:10
----
10:10
WN2386
----
15:50
15:50
----
----
----
----
WN1930
21:15
----
----
21:15
21:15
18:10
21:15

The timetable & schedule information was updated at 2026-09-28

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Chicago to San Jose scheduled departures

Select a date to see every published non-stop departure between MDW and SJC.

Friday
Fri
Oct 30
2 flights(2)
Saturday
Sat
Oct 31
1 flights(1)
Sunday
Sun
Nov 01
2 flights(2)
Monday
Mon
Nov 02
2 flights(2)
Tuesday
Tue
Nov 03
2 flights(2)
Wednesday
Wed
Nov 04
2 flights(2)
Thursday
Thu
Nov 05
2 flights(2)
Time
Airline
Flight
09:50
Southwest Airlines Southwest Airlines
WN2990
21:15
Southwest Airlines Southwest Airlines
WN2080
10:35
Southwest Airlines Southwest Airlines
WN2880
10:10
Southwest Airlines Southwest Airlines
WN3035
21:15
Southwest Airlines Southwest Airlines
WN1930
10:10
Southwest Airlines Southwest Airlines
WN3035
21:15
Southwest Airlines Southwest Airlines
WN1930
10:10
Southwest Airlines Southwest Airlines
WN3035
15:50
Southwest Airlines Southwest Airlines
WN2386
10:10
Southwest Airlines Southwest Airlines
WN3035
15:50
Southwest Airlines Southwest Airlines
WN2386
10:10
Southwest Airlines Southwest Airlines
WN3035
21:15
Southwest Airlines Southwest Airlines
WN1930
Arriving at Norman Y Mineta San Jose International
Norman Y Mineta San Jose International
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MDW-SJC flight route
Route map from Chicago, MDW to San Jose, SJC. The distance is 1843 miles or 2965 km.
Chicago - San Jose direct flight map
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MDW - SJC route facts

  • Distance
    1843 miles (2965 km)
  • Flight time
    4 hours and 35 minutes to 4 hours and 50 minutes
  • Airline
    Southwest Southwest
  • Airline alliances
    Low-cost carrier
  • Cabins
    Economy
  • Arrival terminals
    Terminal B
  • Aircraft
    Boeing 737MAX 8 Passenger and Boeing 737-700 Passenger (Scimitar Winglets)

Route FAQ

Southwest Airlines operates non-stop flights from MDW to SJC with 14 weekly departures.

Scheduled flight time from MDW to SJC ranges from 4 hours and 35 minutes to 4 hours and 50 minutes. The route covers 1843 miles (2965 km).

14 weekly departures are currently scheduled on this route, with published departure times ranging from 09:35 to 21:20 depending on the schedule period.

Arrival terminal: Terminal B.

Economy are currently scheduled on non-stop flights for this route.
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