Direct flights from San Jose to Chicago
All flights from SJC to MDW non-stop. There are direct flights from Norman Y Mineta San Jose International (SJC), California, USA to Chicago Midway International (MDW), Illinois, USA with Southwest Airlines. 14 weekly departures are currently scheduled on this route. Departure times range from 06:00 to 23:00 depending on the schedule period. The flight distance is 1843 miles (2965 km). Flight time ranges from 4 hours to 4 hours and 10 minutes.
San Jose
, USA
Flight schedule from San Jose to Chicago 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
The timetable & schedule information was updated at 2026-07-12
San Jose to Chicago scheduled departures
Select a date to see every published non-stop departure between SJC and MDW.
SJC - MDW route facts
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Distance1843 miles (2965 km)
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Flight time4 hours to 4 hours and 10 minutes
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Airline Southwest
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Airline alliancesLow-cost carrier
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CabinsEconomy
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Departure terminalsTerminal B
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AircraftBoeing 737MAX 8 Passenger, Boeing 737-800 (winglets) Passenger/BBJ2 and Boeing 737-700 Passenger (Scimitar Winglets)
Route FAQ
Direct flights from San Jose to IL, USA
From San Jose to Chicago
ORD Chicago O Hare International
