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.
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:
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 11/13/2025, is operated by Frontier Airlines and costs $96
The cheapest roundtrip flight from Chicago to Oakland departs on 10/09/2025, is operated by Frontier Airlines and costs $265
Fastest flight from Chicago to Oakland takes 6h 22m
There are no direct flights on this route.
The distance between Chicago and Oakland is 2971km (1842 miles). There are 9 direct flights from Chicago to Oakland. The time difference between Chicago and Oakland is 2h. Flights from Chicago begin at 7:20 AM. The latest flight from Chicago departs at 9:30 PM
The Chicago — Oakland route is served by a wide range of airlines: 5 in total, including American Airlines, Southwest Airlines, United Airlines, Frontier Airlines, and Spirit Airlines. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $96. Our service helps compare all available offers within seconds and choose the most convenient option. You can filter flights by price, departure time, or baggage rules to make your trip as comfortable as possible. With so many airlines, there’s always a chance to catch special promotions and save.
Starting at $167
Starting at $187
Starting at $212
Starting at $96
Starting at $156
Chicago — San Francisco
10/08/2025
Departure
Direct flight
AA2113
Starting at $283
Chicago — San Francisco
10/10/2025
Departure
Direct flight
WN1193
Starting at $384
Chicago — San Francisco
10/17/2025
Departure
Direct flight
WN1193
Starting at $286
Chicago — San Francisco
10/20/2025
Departure
Direct flight
UA249
Starting at $438
Chicago — San Francisco
10/24/2025
Departure
Direct flight
UA1387
Starting at $297
Chicago — San Francisco
10/26/2025
Departure
Direct flight
AA2113
Starting at $167
Chicago — San Francisco
11/10/2025
Departure
Direct flight
WN3780
Starting at $187
Chicago — San Francisco
11/13/2025
Departure
Direct flight
UA2179
Starting at $218
Chicago — San Francisco
11/23/2025
Departure
Direct flight
UA210
Starting at $212
Unable to find information about the schedule of direct flights from
We couldn't find any special offers for flights from Chicago to Oakland
The cheapest flight ticket from Chicago to Oakland according to data for the last 48 hours costs $96
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: November, October, February.
The fastest flights from Chicago to Oakland start from 6 hours 22 minutes in the air.
The following airlines operate direct flights on the route Chicago — Oakland: American Airlines, Southwest Airlines, United Airlines
The minimum one-way ticket price from Chicago to Oakland is $130 (November 2025), while the maximum is $169 (February 2026). On average, a ticket costs $144–$301.