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Cheap flights from Oakland (OAK) 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 Oakland (OAK) to Chicago (CHI)

How to find the cheapest flight from Oakland (OAK) to Chicago (CHI)
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How to find the cheapest flight from Oakland (OAK) to Chicago (CHI)
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How to find the cheapest flight from Oakland (OAK) to Chicago (CHI)
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Cheap flights from Oakland to Chicago in September , October 2026

29 Sep - 31 Oct $ 447.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
Pick dates
29 Sep - 10 Oct $ 525.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
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28 Sep - 03 Oct $ 559.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
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Last minute flights from Oakland to Chicago

29 Sep - 30 Sep $ 537.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
Pick dates
29 Sep - 30 Sep $ 537.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
Pick dates
28 Sep - 30 Sep $ 559.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
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One-way flights to Chicago from Oakland

6:51 PM - 11:50 PM
Frontier Airlines
1 Stops
8h 47m
OAK - CHI
$ 214
Kiwi
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2:15 PM - 5:51 PM
Alaska Airlines
1 Stops
7h 44m
OAK - CHI
$ 269
Kiwi
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3:13 PM - 5:45 PM
Alaska Airlines
1 Stops
6h 46m
OAK - CHI
$ 291
Kiwi
Pick dates

How to find the cheapest flight from Oakland (OAK) to Chicago (CHI)

Related info for your journey
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How to find the cheapest flight from Oakland (OAK) 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 Oakland (OAK) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.