Earn point on your loyalty program!arrow arc left

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

Know your dates, get live prices in seconds
airplane logo

pin logo

calendar
Departure
calendar backward
Return
airplane logo
1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
Book Flight + Hotel at the same time

How to find the cheapest flight from Chicago (CHI) to Oakland (OAK)

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.
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.

Cheap flights from Chicago to Oakland in March , April 2026

24 Mar - 22 Apr $ 371.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
09 Mar - 07 Apr $ 415.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
07 Mar - 06 Apr $ 6,719.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
2 STOPS
CHI
Chicago
Pick dates

Last minute flights from Chicago to Oakland

24 Mar - 31 Mar $ 417.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
10 Mar - 31 Mar $ 423.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
07 Mar - 31 Mar $ 530.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates

One-way flights to Oakland from Chicago

2:09 PM - 5:35 PM
Hawaiian Airlines
1 Stops
7h 16m
CHI - OAK
$ 235
Kiwi
Pick dates
5:29 PM - 9:45 PM
Alaska Airlines
1 Stops
8h 29m
CHI - OAK
$ 239
Kiwi
Pick dates
5:29 PM - 9:45 PM
Alaska Airlines
1 Stops
8h 25m
CHI - OAK
$ 353
Kiwi
Pick dates

How to find the cheapest flight from Chicago (CHI) to Oakland (OAK)

Related info for your journey
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.
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.