Cheap flights from Chicago O'Hare Intl Airport to San Francisco from $105

The month of April is, on average, the cheapest month to fly to Oakland, California from Chicago O'Hare Intl Airport, with most prices found around $264. If you aren’t able to travel to Oakland, California during the month of April, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $276.

According to our data, Wednesday is the cheapest day to fly to Oakland, California from Chicago O'Hare Intl Airport. 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 O'Hare Intl Airport to Oakland, California for around $711.

In the evening is the cheapest time of day to fly from Chicago O'Hare Intl Airport 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 $609.

As of August 2026, prices for Chicago O'Hare Intl Airport to Oakland, California flights are approximately 70% more expensive when compared to flights at the same time last year.

Frontier and Alaska Airlines are the most popular carriers operating from Chicago O'Hare Intl to Oakland

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Oakland, California from Chicago O'Hare Intl Airport according to our data. United Airlines is the first choice among our users, with 60% 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 10% 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 76 minutes.

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

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