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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 May , June 2026

29 May - 10 Jun $ 382.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
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24 May - 10 Jun $ 423.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
24 May - 10 Jun $ 478.00
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

24 May - 31 May $ 502.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
25 May - 01 Jun $ 530.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
25 May - 31 May $ 766.00
SJC
San Jose
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
SJC
San Jose
Pick dates

One-way flights to Chicago from San Jose

2:00 PM - 5:44 PM
Alaska Airlines
1 Stops
7h 55m
SJC - CHI
$ 270
Kiwi
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6:30 AM - 6:30 AM
United Airlines
0 Stops
4h 24m
SJC - CHI
$ 279
Kiwi
Pick dates
6:30 AM - 6:30 AM
United Airlines
0 Stops
4h 22m
SJC - CHI
$ 655
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.