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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 December 2025 , January 2026

21 Dec - 14 Jan $ 404.00
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
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22 Dec - 07 Jan $ 529.00
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
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22 Dec - 08 Jan $ 659.00
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

22 Dec - 31 Dec $ 652.00
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
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23 Dec - 31 Dec $ 692.00
CHI
Chicago
United Airlines
DIRECT
SJC
San Jose
SJC
San Jose
United Airlines
1 STOPS
CHI
Chicago
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23 Dec - 31 Dec $ 781.00
CHI
Chicago
United Airlines
DIRECT
SJC
San Jose
SJC
San Jose
United Airlines
1 STOPS
CHI
Chicago
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One-way flights to San Jose from Chicago

12:45 PM - 5:06 PM
Frontier Airlines
1 Stops
8h 3m
CHI - SJC
$ 321
Kiwi
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3:37 PM - 8:56 PM
Alaska Airlines
1 Stops
9h 2m
CHI - SJC
$ 368
Kiwi
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7:35 PM - 7:35 PM
United Airlines
0 Stops
4h 59m
CHI - SJC
$ 615
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.