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 most convenient and comfortable way to fly from Oakland to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Oakland to Chicago:
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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
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San Francisco — Chicago
12/16/2025
Departure
Direct flight
AA1353
Starting at $256
San Francisco — Chicago
12/16/2025
Departure
Direct flight
UA2243
Starting at $184
San Francisco — Chicago
01/19/2026
Departure
Direct flight
UA1184
Starting at $361
San Francisco — Chicago
01/24/2026
Departure
Direct flight
UA1288
Starting at $143
San Francisco — Chicago
03/17/2026
Departure
Direct flight
AA2614
Starting at $131
San Francisco — Chicago
12/11/2025
Departure
Direct flight
UA1557
Starting at $620
San Francisco — Chicago
12/12/2025
Departure
Direct flight
UA2231
Starting at $463
San Francisco — Chicago
12/13/2025
Departure
Direct flight
UA2243
Starting at $323
Starting at $131
Starting at $143
Starting at $70
Starting at $131
Starting at $136
The route Oakland — Chicago is served by many carriers — 5 in total, including American Airlines, United Airlines, Frontier Airlines, Alaska Airlines, and Southwest Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $70) 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 01/24/2026, is operated by Frontier Airlines and costs $70
The cheapest roundtrip flight from Oakland to Chicago departs on 12/17/2025, is operated by Southwest Airlines and costs $310
Fastest flight from Oakland to Chicago takes 4h 5m
There are direct flights on this route 1 day a week: Tu
The distance between Oakland and Chicago is 2971km (1842 miles). There are 9 direct flights from Oakland to Chicago. The time difference between Oakland and Chicago is 2h. Flights from Oakland begin at 5:10 AM. The latest flight from Oakland departs at 1:30 PM
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 $70
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: January, December.
The fastest flights from Oakland to Chicago start from 4 hours 5 minutes in the air.
The following airlines operate direct flights on the route Oakland — Chicago: American Airlines, United Airlines
In different months, ticket prices from Oakland to Chicago vary: minimum — $142 (January 2026), maximum — $250 (December 2025). Typically, the flight costs $196–$250.
