Airlines operating on route
Below you will find a list of airlines operating flights on the Chicago — Oakland route and the starting prices for flights of each specific airline on it.
Starting at $180
Helping travelers to find the best flight offers
Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Chicago to Oakland. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Chicago to Oakland
Below you will find a list of airlines operating flights on the Chicago — Oakland route and the starting prices for flights of each specific airline on it.
Starting at $180
A direct flight is the most convenient and comfortable way to fly from Chicago to Oakland, despite the fact that sometimes flights with transfers can cost significantly less.
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Chicago to Oakland:
Unable to find information about the schedule of direct flights from
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
The cheapest one-way flight from Chicago to Oakland departs on 06/11/2025, is operated by American Airlines and costs $89
The cheapest roundtrip flight from Chicago to Oakland departs on 04/16/2025, is operated by Frontier Airlines and costs $148
Fastest flight from Chicago to Oakland takes 4h 39m
There are direct flights on this route 2 days a week: We and Fr
The distance between Chicago and Oakland is 2971km (1842 miles). There are 8 direct flights from Chicago to Oakland. The time difference between Chicago and Oakland is 2h . Flights from Chicago begin at 12:50 PM. The latest flight from Chicago departs at 9:10 PM.
We couldn't find any special offers for flights from Chicago to Oakland
Chicago — San Francisco
04/24/2025
Departure date
Direct flight
UA343
Starting at $254
Chicago — San Francisco
05/06/2025
Departure date
Direct flight
UA1815
Starting at $277
Chicago — San Francisco
05/14/2025
Departure date
Direct flight
WN2276
Starting at $176
Chicago — San Francisco
06/25/2025
Departure date
Direct flight
UA336
Starting at $208
Chicago — San Francisco
06/11/2025
Departure date
Direct flight
AA2113
Starting at $89
Chicago — San Francisco
04/23/2025
Departure date
Direct flight
AS597
Starting at $284
Chicago — San Francisco
09/12/2025
Departure date
Direct flight
AS597
Starting at $173
Chicago — San Francisco
10/12/2025
Departure date
Direct flight
HA6199
Starting at $295
Chicago — Oakland
04/26/2025
Departure date
Direct flight
WN2937
Starting at $209
The cheapest flight ticket from Chicago to Oakland according to data for the last 48 hours costs $89
Often the best time to buy tickets from Chicago to Oakland is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Chicago to Oakland can be found flying in these months: April, September, May.
The fastest flights from Chicago to Oakland start from 4 hours 39 minutes in the air.
The following airlines operate direct flights on the route Chicago — Oakland: United Airlines, Southwest Airlines, American Airlines
