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

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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 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 April , May 2026

28 Apr - 04 May $ 270.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
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08 Apr - 06 May $ 401.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
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08 Apr - 04 May $ 401.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
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Last minute flights from Chicago to Oakland

28 Apr - 30 Apr $ 376.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
08 Apr - 30 Apr $ 487.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
08 Apr - 30 Apr $ 507.00
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

8:50 AM - 1:00 PM
Alaska Airlines
1 Stops
7h 48m
CHI - OAK
$ 128
Kiwi
Pick dates
2:09 PM - 5:35 PM
Alaska Airlines
1 Stops
7h 16m
CHI - OAK
$ 259
Kiwi
Pick dates
2:09 PM - 5:35 PM
Alaska Airlines
1 Stops
7h 16m
CHI - OAK
$ 259
Kiwi
Pick dates

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.