Direct flights from Chicago to San Jose
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 25 minutes to 4 hours and 50 minutes.
Chicago
, USA
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
The timetable & schedule information was updated at 2026-08-24
Chicago to San Jose scheduled departures
Select a date to see every published non-stop departure between MDW and SJC.
MDW - SJC route facts
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Distance1843 miles (2965 km)
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Flight time4 hours and 25 minutes to 4 hours and 50 minutes
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Airline Southwest
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Airline alliancesLow-cost carrier
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CabinsEconomy
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Arrival terminalsTerminal B
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AircraftBoeing 737MAX 8 Passenger and Boeing 737-700 Passenger (Scimitar Winglets)
Route FAQ
Direct flights from Chicago to CA, USA
From Chicago to Oakland
OAK Metropolitan Oakland International
From Chicago to San Francisco
SFO San Francisco International
From Chicago to Sacramento
SMF Sacramento International
From Chicago to Burbank
BUR Burbank Glendale Pasadena
From Chicago to Los Angeles
LAX Los Angeles International
From Chicago to Long Beach
LGB Long Beach
From Chicago to San Diego
SAN San Diego International Airport
From Chicago to Ontario
ONT Ontario International Airport
From Chicago to Palm Springs
PSP Palm Springs International
