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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 July , August 2026

31 Jul - 15 Aug $ 407.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
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31 Jul - 07 Aug $ 643.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
28 Jul - 04 Aug $ 710.00
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 Jul - 31 Jul $ 709.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
28 Jul - 31 Jul $ 710.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
31 Jul - 31 Jul $ 867.00
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

9:09 AM - 5:23 PM
Alaska Airlines
1 Stops
12h 27m
SJC - CHI
$ 410
Kiwi
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3:15 PM - 5:23 PM
Alaska Airlines
1 Stops
6h 21m
SJC - CHI
$ 432
Kiwi
Pick dates
6:30 AM - 6:30 AM
United Airlines
0 Stops
4h 24m
SJC - CHI
$ 665
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.