Helping travelers to find the best flight offers
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 Oakland to Chicago
Below you will find a list of airlines operating flights on the Oakland — Chicago route and the starting prices for flights of each specific airline on it.
Starting at $82
Starting at $92
Starting at $105
Starting at $141
Starting at $147
San Francisco — Chicago
01/08/2026
Departure date
Direct flight
AA2614
Starting at $116
San Francisco — Chicago
12/16/2025
Departure date
Direct flight
UA1791
Starting at $275
Oakland — Chicago
11/10/2025
Departure date
Direct flight
WN2363
Starting at $216
Oakland — Chicago
11/12/2025
Departure date
Direct flight
WN1772
Starting at $261
Oakland — Chicago
11/13/2025
Departure date
Direct flight
WN2363
Starting at $216
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Oakland to Chicago:
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.
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 Oakland to Chicago. 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 Oakland to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
The cheapest flight ticket from Oakland to Chicago according to data for the last 48 hours costs $98
Often the best time to buy tickets from Oakland to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Oakland to Chicago can be found flying in these months: June, December, July.
The fastest flights from Oakland to Chicago start from 4 hours 23 minutes in the air.
The following airlines operate direct flights on the route Oakland — Chicago: American Airlines, United Airlines, Southwest Airlines
The cheapest one-way flight from Oakland to Chicago departs on 11/12/2025, is operated by Spirit Airlines and costs $98
The cheapest roundtrip flight from Oakland to Chicago departs on 05/17/2025, is operated by United Airlines and costs $257
Fastest flight from Oakland to Chicago takes 4h 23m
There are direct flights on this route 1 day a week: Th
The distance between Oakland and Chicago is 2971km (1842 miles). There are 8 direct flights from Oakland to Chicago. The time difference between Oakland and Chicago is 2h . Flights from Oakland begin at 5:05 AM. The latest flight from Oakland departs at 6:05 AM.
We couldn't find any special offers for flights from Oakland to Chicago
