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

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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 November , December 2026

18 Nov - 05 Dec $ 447.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
Pick dates
18 Nov - 09 Dec $ 451.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
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18 Nov - 08 Dec $ 451.00
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

17 Nov - 01 Dec $ 553.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
Pick dates
17 Nov - 01 Dec $ 553.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
Pick dates
18 Nov - 30 Nov $ 1,421.00
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

12:57 PM - 5:51 PM
Alaska Airlines
1 Stops
9h 2m
OAK - CHI
$ 275
Kiwi
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10:00 AM - 12:41 PM
Alaska Airlines
1 Stops
6h 59m
OAK - CHI
$ 277
Kiwi
Pick dates
10:00 AM - 12:41 PM
Alaska Airlines
1 Stops
6h 59m
OAK - CHI
$ 282
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.