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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)
Save up to 31%
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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 August , September 2026

31 Aug - 06 Sep $ 313.00
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
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29 Aug - 11 Sep $ 357.00
CHI
Chicago
Frontier Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Frontier Airlines
1 STOPS
CHI
Chicago
Pick dates
28 Aug - 10 Sep $ 418.00
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

29 Aug - 31 Aug $ 492.00
CHI
Chicago
Frontier Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Frontier Airlines
1 STOPS
CHI
Chicago
Pick dates
28 Aug - 31 Aug $ 514.00
CHI
Chicago
Frontier Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Frontier Airlines
1 STOPS
CHI
Chicago
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27 Aug - 31 Aug $ 737.00
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

6:00 AM - 1:55 PM
Alaska Airlines
1 Stops
12h 15m
CHI - SJC
$ 257
Kiwi
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2:18 PM - 5:39 PM
Alaska Airlines
1 Stops
6h 51m
CHI - SJC
$ 279
Kiwi
Pick dates
9:00 AM - 9:00 AM
United Airlines
0 Stops
4h 46m
CHI - SJC
$ 369
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.