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 November , December 2025

25 Nov - 10 Dec $ 438.00
CHI
Chicago
Hawaiian Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Hawaiian Airlines
1 STOPS
CHI
Chicago
Pick dates
25 Nov - 10 Dec $ 447.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
22 Nov - 01 Dec $ 610.00
CHI
Chicago
Hawaiian Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Hawaiian Airlines
1 STOPS
CHI
Chicago
Pick dates

Last minute flights from Chicago to Oakland

25 Nov - 01 Dec $ 643.00
CHI
Chicago
Volaris
1 STOPS
OAK
Oakland
OAK
Oakland
Volaris
1 STOPS
CHI
Chicago
Pick dates
22 Nov - 01 Dec $ 980.00
CHI
Chicago
Alaska Airlines
1 STOPS
OAK
Oakland
OAK
Oakland
Alaska Airlines
1 STOPS
CHI
Chicago
Pick dates
22 Nov - 30 Nov $ 1,019.00
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

6:00 AM - 11:31 AM
Hawaiian Airlines
1 Stops
9h 46m
CHI - OAK
$ 295
Kiwi
Pick dates
8:00 AM - 11:31 AM
Alaska Airlines
1 Stops
7h 46m
CHI - OAK
$ 305
Kiwi
Pick dates
2:10 PM - 5:33 PM
Alaska Airlines
1 Stops
7h 9m
CHI - OAK
$ 345
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.