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 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.
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Chicago to Oakland:
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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
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.
The cheapest one-way flight from Chicago to Oakland departs on 12/03/2025, is operated by Alaska Airlines and costs $108
The cheapest roundtrip flight from Chicago to Oakland departs on 12/20/2025, is operated by Frontier Airlines and costs $328
Fastest flight from Chicago to Oakland takes 4h 52m
There are direct flights on this route 1 day a week: We
The distance between Chicago and Oakland is 2971km (1842 miles). There are 9 direct flights from Chicago to Oakland. The time difference between Chicago and Oakland is 2h. Flights from Chicago begin at 7:45 AM. The latest flight from Chicago departs at 7:50 PM
The minimum one-way ticket price from Chicago to Oakland is $144 (February 2026), while the maximum is $360 (November 2025). On average, a ticket costs $227–$536.
Chicago — San Francisco
11/26/2025
Departure
Direct flight
UA448
Starting at $594
Chicago — San Francisco
11/27/2025
Departure
Direct flight
UA1498
Starting at $635
Chicago — San Francisco
11/30/2025
Departure
Direct flight
UA1577
Starting at $1,035
Chicago — San Francisco
12/02/2025
Departure
Direct flight
UA2866
Starting at $420
Chicago — San Francisco
12/04/2025
Departure
Direct flight
WN3780
Starting at $318
Chicago — San Francisco
12/24/2025
Departure
Direct flight
WN2176
Starting at $184
Chicago — San Francisco
12/26/2025
Departure
Direct flight
UA210
Starting at $357
Chicago — San Francisco
01/05/2026
Departure
Direct flight
UA1807
Starting at $166
Chicago — San Francisco
02/18/2026
Departure
Direct flight
UA1318
Starting at $331
Chicago — San Francisco
03/18/2026
Departure
Direct flight
WN2181
Starting at $154
Starting at $166
Starting at $154
Starting at $108
Starting at $112
Starting at $277
The Chicago — Oakland route is served by a wide range of airlines: 5 in total, including United Airlines, Southwest Airlines, Alaska Airlines, Frontier Airlines, and Sun Country Airlines. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $108. Our service helps compare all available offers within seconds and choose the most convenient option. You can filter flights by price, departure time, or baggage rules to make your trip as comfortable as possible. With so many airlines, there’s always a chance to catch special promotions and save.
The cheapest flight ticket from Chicago to Oakland according to data for the last 48 hours costs $108
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: February, May, November.
The fastest flights from Chicago to Oakland start from 4 hours 52 minutes in the air.
The following airlines operate direct flights on the route Chicago — Oakland: United Airlines, Southwest Airlines
We couldn't find any special offers for flights from Chicago to Oakland
