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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 August , September 2026

31 Aug - 09 Sep $ 373.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
20 Aug - 09 Sep $ 377.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
26 Aug - 04 Sep $ 542.00
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

20 Aug - 31 Aug $ 530.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
27 Aug - 31 Aug $ 557.00
SJC
San Jose
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
SJC
San Jose
Pick dates
25 Aug - 31 Aug $ 737.00
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

1:02 PM - 12:56 PM
Frontier Airlines
1 Stops
28h
SJC - CHI
$ 233
Kiwi
Pick dates
10:12 AM - 1:03 PM
Alaska Airlines
1 Stops
7h 9m
SJC - CHI
$ 279
Kiwi
Pick dates
6:20 AM - 6:20 AM
United Airlines
0 Stops
4h 25m
SJC - CHI
$ 369
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.