Chicago to San Jose

MDWSJC

Fly from Chicago to San Jose starting at USD 121 with Southwest Airlines.Best fare available on Sep 17, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to San Jose cheapest flights this week

11 Sept
Frontier Airlines
06:25MDW
21:53SJC
2 StopUSD 212VIEW DEAL
17 Sept
Southwest Airlines
20:50MDW
01:25SJC
DirectUSD 121VIEW DEAL
19 Sept
Southwest Airlines
18:25MDW
22:55SJC
DirectUSD 122VIEW DEAL
22 Sept
Southwest Airlines
10:20MDW
14:45SJC
DirectUSD 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
31 May
Volaris
19:17MDW
01:54SJC
2 StopUSD 755VIEW DEAL

Chicago to San Jose monthly flight fare trend

Sep
from USD 121
Oct
No flights
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

Flights from Chicago

Flights from Chicago to AtlantaFlights from Chicago to AustinFlights from Chicago to BostonFlights from Chicago to CharlotteFlights from Chicago to DenverFlights from Chicago to DallasFlights from Chicago to DetroitFlights from Chicago to NewarkFlights from Chicago to Fort LauderdaleFlights from Chicago to Honolulu