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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 October , November 2026

28 Oct - 18 Nov $ 496.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
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28 Oct - 10 Nov $ 510.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
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29 Oct - 10 Nov $ 512.00
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

29 Oct - 31 Oct $ 615.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
27 Oct - 31 Oct $ 615.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
29 Oct - 31 Oct $ 911.00
SJC
San Jose
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
SJC
San Jose
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One-way flights to Chicago from San Jose

9:15 AM - 12:35 PM
Alaska Airlines
1 Stops
7h 38m
SJC - CHI
$ 305
Kiwi
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8:44 PM - 11:41 PM
Alaska Airlines
1 Stops
6h 56m
SJC - CHI
$ 308
Kiwi
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2:14 PM - 2:14 PM
United Airlines
0 Stops
4h 16m
SJC - CHI
$ 453
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.