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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)
Save up to 31%
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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 June , July 2026

30 Jun - 04 Jul $ 310.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
19 Jun - 01 Jul $ 410.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
10 Jun - 12 Jul $ 1,062.00
SJC
San Jose
United Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
SJC
San Jose
Pick dates

Last minute flights from San Jose to Chicago

23 Jun - 30 Jun $ 365.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
19 Jun - 30 Jun $ 502.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
16 Jun - 30 Jun $ 983.00
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

4:00 PM - 9:05 PM
United Airlines
1 Stops
6h 44m
SJC - CHI
$ 194
Kiwi
Pick dates
3:15 PM - 5:23 PM
Alaska Airlines
1 Stops
6h 21m
SJC - CHI
$ 274
Kiwi
Pick dates
6:30 AM - 6:30 AM
United Airlines
0 Stops
4h 24m
SJC - CHI
$ 441
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.