Cheap flights from Chicago to San Francisco from $119

The month of August is, on average, the cheapest month to fly to Oakland, California from Chicago, with most prices found around $83. If you aren’t able to travel to Oakland, California during the month of August, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $86.

According to our data, Wednesday is the cheapest day to fly to Oakland, California from Chicago. The lowest ticket price found for a Wednesday departure recently was $408. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Oakland, California for around $713.

In the evening is the cheapest time of day to fly from Chicago to Oakland, California when you can find flight prices for as low as $332. Flying to Oakland, California in the evening is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $613.

Fly from Chicago Midway to Oakland for the best Chicago - Oakland flight prices

There is only 1 cabin class available to choose from on Chicago to Oakland, California flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

As of July 2026, prices for Chicago to Oakland, California flights are approximately 92% more expensive when compared to flights at the same time last year.

Southwest, Alaska Airlines, and Delta are the most popular carriers operating from Chicago to Oakland

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Oakland, California from Chicago according to our data. United Airlines is the first choice among our users, with 55% of people opting to fly with this airline when traveling to Oakland, California. Keep in mind that there are 7 different airlines that fly to Oakland, California on a routine basis, so you have a few additional options to choose from.

Historically, on average around 25% of flights between Chicago and Oakland have experienced a delay on any given week. The average delay length over the past 12 months has been 104 minutes.

Generally, flights departing in the early afternoon tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Thursday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 30% of their flights experiencing any sort of delay.

Las Vegas (LAS) was the most common stop: 67% of momondo users choosing 1-stop flights on this route connected there.

Flights via Las Vegas (LAS) offer the lowest average round-trip price of $336.

Flights connecting via Las Vegas (LAS) have the shortest average one-way travel time: 6h 50m.

Las Vegas (LAS) has the shortest average layover time for this route: 1h 43m.

3 flights are operational daily from Chicago to Oakland, California as of July 2026. The most popular departure time for this route is 10:00AM, with 35% of flights per day taking off at noon.

As of July 2026, 22 flights take off from Chicago and land in Oakland, California each week. The most common flight departure day for this route is Mon, with 23% of weekly flights taking off on this day.