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
14 May
WN
20:25MDW
01:00SJC
Direct$151VIEW DEAL
17 Jun
WN
06:00MDW
13:25SJC
1 Stop$137VIEW DEAL
24 Jun
WN
05:35MDW
12:40SJC
1 Stop$137VIEW DEAL
Chicago to San Jose monthly flight fare trend
May
from USD 151
Jun
from USD 137
Jul
No flights
Aug
No flights
Sep
No flights
Oct
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
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