Chicago to San Jose
MDWSJC
Fly from Chicago to San Jose starting at USD 137 with WN.
Best fare available on Jun 17, 2026.
Limited seats. Better plans. Book before it's gone.
Chicago to San Jose cheapest flights this week
23 Apr
F9
06:00MDW
--:--SJC
2 Stop$322VIEW DEAL
17 Jun
WN
06:00MDW
--:--SJC
1 Stop$137VIEW DEAL
24 Jun
WN
05:35MDW
--:--SJC
1 Stop$137VIEW DEAL
Chicago to San Jose monthly flight fare trend
Apr
from USD 322
May
No flights
Jun
from USD 137
Jul
No flights
Aug
No flights
Sep
No flights
Airport Details
Origin
Chicago
Chicago Midway International Airport (MDW)
Chicago, MDW
Zone
Chicago
Elev
620 ft
Destination
San Jose
Norman Y. Mineta San Jose International Airport (SJC)
San Jose, SJC
Zone
Los Angeles
Elev
62 ft
