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

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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 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 March , April 2026

31 Mar - 28 Apr $ 366.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
Pick dates
11 Mar - 01 Apr $ 414.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
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11 Mar - 08 Apr $ 481.00
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

11 Mar - 31 Mar $ 451.00
OAK
Oakland
Hawaiian Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Hawaiian Airlines
1 STOPS
OAK
Oakland
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11 Mar - 31 Mar $ 553.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
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12 Mar - 31 Mar $ 651.00
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

7:00 AM - 12:12 PM
Alaska Airlines
1 Stops
9h 26m
OAK - CHI
$ 235
Kiwi
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6:15 AM - 10:22 AM
Alaska Airlines
1 Stops
8h 18m
OAK - CHI
$ 247
Kiwi
Pick dates
6:15 AM - 10:22 AM
Alaska Airlines
1 Stops
8h 18m
OAK - CHI
$ 345
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.