There are most likely no direct flights on the Chicago — Oakland route
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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.
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There are most likely no direct flights on the Chicago — Oakland route
The minimum one-way ticket price from Chicago to Oakland is $118 (July 2026), while the maximum is $126 (September 2026). On average, a ticket costs $122–$126.
Chicago — San Francisco
08/03/2026
Departure
Direct flight
AA3054
starting at $662
Chicago — San Francisco
08/21/2026
Departure
Direct flight
UA511
starting at $239
The route Chicago — Oakland is served by several airlines: American Airlines, United Airlines, 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 $137 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.
The cheapest flight ticket from Chicago to Oakland according to data for the last 48 hours costs $137
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: July, September.
The fastest flights from Chicago to Oakland start from 9 hours 13 minutes in the air.
The following airlines operate direct flights on the route Chicago — Oakland: American Airlines, United Airlines
The cheapest one-way flight from Chicago to Oakland departs on 08/21/2026, is operated by Frontier Airlines and costs $137
There is no information about the cheapest roundtrip flight from Chicago to Oakland
Fastest flight from Chicago to Oakland takes 9h 13m
There are direct flights on this route 2 days a week: Mo and Fr
The distance between Chicago and Oakland is 2971km (1842 miles). There are 12 direct flights from Chicago to Oakland. The time difference between Chicago and Oakland is 2h. Flights from Chicago begin at 10:00 AM. The latest flight from Chicago departs at 9:40 PM
We couldn't find any special offers for flights from Chicago to Oakland