Unable to find information about the schedule of direct flights from
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 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 easiest way to get to your destination. The following airlines operate non-stop flights from Oakland to Chicago:
•
•
•
•
•
•
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.
Unable to find information about the schedule of direct flights from
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.
San Francisco — Chicago
12/16/2025
Departure
Direct flight
AA1353
Starting at $252
Oakland — Chicago
12/26/2025
Departure
Direct flight
WN3808
Starting at $250
Starting at $252
Starting at $189
Starting at $136
Starting at $381
The route Oakland — Chicago is served by many carriers — 4 in total, including American Airlines, Southwest Airlines, Frontier Airlines, and VivaAerobus. This gives passengers wide opportunities: from finding the lowest fare (from $136) to selecting flights by schedule or service class. Our service aggregates data from multiple booking systems so you can compare offers in one place. This saves time and money: no need to check dozens of sites — just pick the right option and book online.
The cheapest one-way flight from Oakland to Chicago departs on 12/15/2025, is operated by Frontier Airlines and costs $136
There is no information about the cheapest roundtrip flight from Oakland to Chicago
Fastest flight from Oakland to Chicago takes 6h 25m
There are no direct flights on this route.
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 5:25 AM. The latest flight from Oakland departs at 11:00 AM
We couldn't find any special offers for flights from Oakland to Chicago
The cheapest flight ticket from Oakland to Chicago according to data for the last 48 hours costs $136
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: December.
The fastest flights from Oakland to Chicago start from 6 hours 25 minutes in the air.
The following airlines operate direct flights on the route Oakland — Chicago: American Airlines, Southwest Airlines
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
