Cheap flights from Chicago to San Francisco from $109

The month of April is, on average, the cheapest month to fly to Oakland, California from Chicago, with most prices found around $327. If you aren’t able to travel to Oakland, California during the month of April, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $329.

According to our data, Saturday is the cheapest day to fly to Oakland, California from Chicago. The lowest ticket price found for a Saturday departure recently was $365. 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 $699.

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 $350. 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 $599.

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.

You could potentially save up to 11% on your flight if you consider stops on a Chicago to Oakland, California flight.

Southwest and Alaska Airlines 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 58% 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 27% 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 105 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. Friday 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 33% of their flights experiencing any sort of delay.

1 flights are operational daily from Chicago to Oakland, California as of November 2026. The most popular departure time for this route is 10:00AM, with 40% of flights per day taking off at noon.

As of November 2026, 9 flights take off from Chicago and land in Oakland, California each week. The most common flight departure day for this route is Mon, with 22% of weekly flights taking off on this day.