Chicago to San Jose

MDWSJC

Fly from Chicago to San Jose starting at USD 139 with Southwest Airlines.Best fare available on Feb 1, 2027.Limited seats. Better plans. Book before it's gone.

Chicago to San Jose cheapest flights this week

12 Oct
Southwest Airlines
22:55MDW
09:20SJC
1 StopUSD 194VIEW DEAL
15 Nov
Southwest Airlines
10:10MDW
14:55SJC
DirectUSD 219VIEW DEAL
29 Nov
Southwest Airlines
23:10MDW
15:25SJC
1 StopUSD 363VIEW DEAL
1 Feb
Southwest Airlines
20:00MDW
00:45SJC
DirectUSD 139VIEW DEAL
17 Feb
Southwest Airlines
10:15MDW
15:05SJC
DirectUSD 183VIEW DEAL
31 May
Volaris
19:17MDW
01:54SJC
2 StopUSD 755VIEW DEAL

Chicago to San Jose monthly flight fare trend

Sep
No flights
Oct
from USD 194
Nov
from USD 219
Dec
No flights
Jan
No flights
Feb
from USD 139

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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