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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.
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.
We couldn't find any special offers for flights from Chicago to Oakland
The cheapest one-way flight from Chicago to Oakland departs on 09/29/2025, is operated by United Airlines and costs $141
The cheapest roundtrip flight from Chicago to Oakland departs on 12/26/2024, is operated by Southwest Airlines and costs $301
Fastest non-stop flight from Chicago to Oakland takes 4h 35m
There are direct flights on this route 2 days a week: Mo and Sa
The cheapest flight ticket from Chicago to Oakland according to data for the last 48 hours costs $141
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: January, September, May.
The fastest flights from Chicago to Oakland start from 4 hours 35 minutes in the air.
The following airlines operate direct flights on the route Chicago — Oakland: American Airlines, United Airlines, Southwest Airlines