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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 April , May 2026

27 Apr - 06 May $ 270.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
Pick dates
09 Apr - 05 May $ 385.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
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05 Apr - 05 May $ 6,808.00
OAK
Oakland
Alaska Airlines
2 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
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Last minute flights from Oakland to Chicago

27 Apr - 30 Apr $ 285.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
Pick dates
07 Apr - 30 Apr $ 401.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
Pick dates
05 Apr - 30 Apr $ 7,036.00
OAK
Oakland
Alaska Airlines
2 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
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One-way flights to Chicago from Oakland

3:18 PM - 5:36 PM
Alaska Airlines
1 Stops
6h 25m
OAK - CHI
$ 142
Kiwi
Pick dates
7:00 AM - 12:12 PM
Alaska Airlines
1 Stops
9h 26m
OAK - CHI
$ 258
Kiwi
Pick dates
7:00 AM - 12:12 PM
Hawaiian Airlines
1 Stops
9h 26m
OAK - CHI
$ 269
Kiwi
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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.