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Cheap flights from Chicago (CHI) to San Jose (SJC)

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1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
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How to find the cheapest flight from Chicago (CHI) to San Jose (SJC)

How to find the cheapest flight from Chicago (CHI) to San Jose (SJC)
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How to find the cheapest flight from Chicago (CHI) to San Jose (SJC)
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How to find the cheapest flight from Chicago (CHI) to San Jose (SJC)
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Cheap flights from Chicago to San Jose in April , May 2026

30 Apr - 02 May $ 285.00
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
18 Apr - 05 May $ 404.00
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
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10 Apr - 15 May $ 1,383.00
CHI
Chicago
United Airlines
DIRECT
SJC
San Jose
SJC
San Jose
United Airlines
DIRECT
CHI
Chicago
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Last minute flights from Chicago to San Jose

16 Apr - 30 Apr $ 396.00
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
16 Apr - 30 Apr $ 460.00
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
16 Apr - 30 Apr $ 729.00
CHI
Chicago
United Airlines
DIRECT
SJC
San Jose
SJC
San Jose
United Airlines
DIRECT
CHI
Chicago
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One-way flights to San Jose from Chicago

8:50 AM - 12:03 PM
Alaska Airlines
1 Stops
6h 54m
CHI - SJC
$ 229
Kiwi
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2:09 PM - 5:32 PM
Alaska Airlines
1 Stops
7h 23m
CHI - SJC
$ 254
Kiwi
Pick dates
3:35 PM - 3:35 PM
United Airlines
0 Stops
4h 55m
CHI - SJC
$ 344
Kiwi
Pick dates

How to find the cheapest flight from Chicago (CHI) to San Jose (SJC)

Related info for your journey
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How to find the cheapest flight from Chicago (CHI) to San Jose (SJC)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Chicago (CHI) to San Jose (SJC)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.