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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 May , June 2026

31 May - 07 Jun $ 402.00
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
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28 May - 08 Jun $ 447.00
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
27 May - 02 Jun $ 502.00
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
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Last minute flights from Chicago to San Jose

27 May - 31 May $ 502.00
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
26 May - 31 May $ 502.00
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
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28 May - 31 May $ 795.00
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

2:18 PM - 5:30 PM
Alaska Airlines
1 Stops
7h 3m
CHI - SJC
$ 274
Kiwi
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9:00 AM - 12:39 PM
Alaska Airlines
1 Stops
7h 13m
CHI - SJC
$ 274
Kiwi
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7:50 PM - 7:50 PM
United Airlines
0 Stops
4h 45m
CHI - SJC
$ 364
Kiwi
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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.