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.
The minimum one-way ticket price from Chicago to Oakland is $136 (October 2026), while the maximum is $192 (May 2027). On average, a ticket costs $140–$151.
A non-stop 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.
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Answers to questions about the route that travelers are most interested in.
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.
Tickets from Chicago to Oakland are getting more expensive each month. From September 2026 to May 2027, the increase reached 41%, with prices now at $192. It's unlikely to get cheaper than the current level.
The most significant price increase was from September 2026 to May 2027 — up 41%. The best time to fly is September 2026–October 2026, when the average price is $136. In November 2026–May 2027, tickets cost around $166.
Given the rising prices, it's best not to delay your purchase. Flying in September 2026–October 2026 can save you up to 18% compared to the most expensive months.
Price variation across months on this route is 15.7%. Your choice of departure month significantly affects the total flight cost.
The route Chicago — Oakland is served by several airlines: American Airlines, Allegiant Air, and Frontier Airlines. This gives passengers more freedom in choosing flights. You can consider not only the price but also schedules, baggage policies, and onboard service. Our service compares all offers so you can find tickets from $154 and choose the most convenient option. Thanks to airline competition, you may also find promotional fares or special offers, helping you save even more. Plan your trip in advance and choose the best flights without overpaying.
Chicago — San Francisco
09/27/2026
Departure
Direct flight
AA2885
starting at $477
There are most likely no direct flights on the Chicago — Oakland route
The cheapest flight ticket from Chicago to Oakland according to data for the last 48 hours costs $154
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: October, September, November.
The fastest flights from Chicago to Oakland start from 13 hours 53 minutes in the air.
The following airlines operate direct flights on the route Chicago — Oakland: American Airlines
All airports
We couldn't find any special offers for flights from Chicago to Oakland
The cheapest one-way flight from Chicago to Oakland departs on 09/28/2026, is operated by Allegiant Air and costs $154
The cheapest roundtrip flight from Chicago to Oakland departs on 10/16/2026, is operated by Frontier Airlines and costs $291
Fastest flight from Chicago to Oakland takes 13h 53m
There are direct flights on this route 1 day a week: Su
The distance between Chicago and Oakland is 2971km (1842 miles). There are 15 direct flights from Chicago to Oakland. The time difference between Chicago and Oakland is 2h. Flights from Chicago begin at 10:15 AM. The latest flight from Chicago departs at 8:35 PM