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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 June , July 2026

29 Jun - 14 Jul $ 315.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
Pick dates
17 Jun - 07 Jul $ 384.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
Pick dates
16 Jun - 07 Jul $ 534.00
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

17 Jun - 30 Jun $ 441.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
Pick dates
29 Jun - 30 Jun $ 454.00
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
Pick dates
10 Jun - 30 Jun $ 534.00
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

7:13 PM - 10:59 PM
Alaska Airlines
1 Stops
7h 47m
OAK - CHI
$ 179
Kiwi
Pick dates
10:37 AM - 5:23 PM
Alaska Airlines
1 Stops
10h 59m
OAK - CHI
$ 247
Kiwi
Pick dates
2:50 PM - 5:23 PM
Alaska Airlines
1 Stops
6h 46m
OAK - CHI
$ 259
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.