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

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0 Children (2~11)
0 Infants (0~2)
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How to find the cheapest flight from Chicago (CHI) to Oakland (OAK)

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

26 Jan - 25 Feb $ 325.00
CHI
Chicago
Hawaiian Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Hawaiian Airlines
1 STOPS
CHI
Chicago
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21 Jan - 02 Feb $ 400.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
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16 Jan - 03 Feb $ 520.00
CHI
Chicago
Hawaiian Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Hawaiian Airlines
1 STOPS
CHI
Chicago
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Last minute flights from Chicago to Oakland

26 Jan - 31 Jan $ 330.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
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21 Jan - 31 Jan $ 582.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
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16 Jan - 31 Jan $ 665.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
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One-way flights to Oakland from Chicago

2:06 PM - 5:32 PM
Alaska Airlines
1 Stops
7h 17m
CHI - OAK
$ 190
Kiwi
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8:00 AM - 2:14 PM
Alaska Airlines
1 Stops
10h 23m
CHI - OAK
$ 239
Kiwi
Pick dates
2:06 PM - 5:32 PM
Alaska Airlines
1 Stops
7h 17m
CHI - OAK
$ 347
Kiwi
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How to find the cheapest flight from Chicago (CHI) to Oakland (OAK)

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