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

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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 San Jose (SJC) to Chicago (CHI)

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

18 Mar - 24 Apr $ 217.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
11 Mar - 01 Apr $ 289.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
09 Mar - 03 Apr $ 336.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
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Last minute flights from San Jose to Chicago

18 Mar - 31 Mar $ 263.00
SJC
San Jose
Hawaiian Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Hawaiian Airlines
1 STOPS
SJC
San Jose
Pick dates
11 Mar - 31 Mar $ 309.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
09 Mar - 31 Mar $ 520.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
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One-way flights to Chicago from San Jose

6:30 AM - 6:30 AM
United Airlines
0 Stops
4h 29m
SJC - CHI
$ 149
Kiwi
Pick dates
12:45 PM - 5:42 PM
Alaska Airlines
1 Stops
9h 14m
SJC - CHI
$ 173
Kiwi
Pick dates
10:55 PM - 10:55 PM
United Airlines
0 Stops
4h 19m
SJC - CHI
$ 334
Kiwi
Pick dates

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

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