San Jose to Chicago
SJCMDW
Fly from San Jose to Chicago starting at USD 294 with Southwest Airlines.
Best fare available on Jul 30, 2026.
Limited seats. Better plans. Book before it's gone.
San Jose to Chicago cheapest flights this week
San Jose to Chicago monthly flight fare trend
Jul
from USD 294
Aug
No flights
Sep
No flights
Oct
No flights
Nov
No flights
Dec
No flights
Airport Details
Origin
San Jose
Norman Y. Mineta San Jose International Airport (SJC)
San Jose, SJC
Zone
Los Angeles
Elev
62 ft
Destination
Chicago
Chicago Midway International Airport (MDW)
Chicago, MDW
Zone
Chicago
Elev
620 ft
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