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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 January , February 2026

31 Jan - 02 Feb $ 283.00
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
20 Jan - 03 Feb $ 420.00
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
15 Jan - 05 Feb $ 683.00
CHI
Chicago
Hawaiian Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Hawaiian Airlines
1 STOPS
CHI
Chicago
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Last minute flights from Chicago to San Jose

29 Jan - 31 Jan $ 344.00
CHI
Chicago
Hawaiian Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Hawaiian Airlines
1 STOPS
CHI
Chicago
Pick dates
20 Jan - 31 Jan $ 422.00
CHI
Chicago
Hawaiian Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
Hawaiian Airlines
1 STOPS
CHI
Chicago
Pick dates
17 Jan - 31 Jan $ 630.00
CHI
Chicago
United Airlines
1 STOPS
SJC
San Jose
SJC
San Jose
United Airlines
1 STOPS
CHI
Chicago
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One-way flights to San Jose from Chicago

9:00 AM - 12:47 PM
Alaska Airlines
1 Stops
7h 21m
CHI - SJC
$ 207
Kiwi
Pick dates
3:44 PM - 8:59 PM
Hawaiian Airlines
1 Stops
8h 51m
CHI - SJC
$ 280
Kiwi
Pick dates
8:45 AM - 11:50 AM
United Airlines
1 Stops
6h 54m
CHI - SJC
$ 377
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.