San Jose to Chicago
SJCMDW
Fly from San Jose to Chicago starting at USD 137 with WN.
Best fare available on Jun 16, 2026.
Limited seats. Better plans. Book before it's gone.
San Jose to Chicago cheapest flights this week
16 Jun
WN
19:35SJC
02:40MDW
1 Stop$137VIEW DEAL
24 Jun
WN
20:55SJC
03:25MDW
1 Stop$137VIEW DEAL
25 Jun
WN
13:50SJC
21:25MDW
1 Stop$229VIEW DEAL
San Jose to Chicago monthly flight fare trend
May
No flights
Jun
from USD 137
Jul
No flights
Aug
No flights
Sep
No flights
Oct
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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