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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 September , October 2026

20 Sep - 15 Oct $ 297.00
CHI
Chicago
Allegiant Air
1 STOPS
OAK
Oakland
OAK
Oakland
Allegiant Air
1 STOPS
CHI
Chicago
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19 Sep - 06 Oct $ 427.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
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19 Sep - 05 Oct $ 428.00
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

25 Sep - 30 Sep $ 458.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
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19 Sep - 30 Sep $ 492.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
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19 Sep - 30 Sep $ 492.00
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

9:29 PM - 7:46 AM
Frontier Airlines
1 Stops
13h 53m
CHI - OAK
$ 135
Kiwi
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2:18 PM - 6:00 PM
Alaska Airlines
1 Stops
7h 34m
CHI - OAK
$ 247
Kiwi
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7:20 AM - 12:40 PM
Alaska Airlines
1 Stops
9h 13m
CHI - OAK
$ 247
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.