Cheap flights from San Francisco to Chicago from $167

If you don’t want to visit Chicago in September, then you should wait until April to fly from San Francisco, when ticket prices are also cheap, with an average price of $465.

Our data shows that Monday is the least expensive day to fly to Chicago. Tickets to fly out on this day can be as low as $620. Flights from San Francisco to Chicago on a Friday will generally be more expensive and average around $858. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Our data shows that the cheapest San Francisco to Chicago flights are usually those with departure times in the evening. Our users have found flights to Chicago in the evening for as low as $555. Flights in the morning are often more expensive, with an average ticket price of $620.

Fly from San Francisco to Chicago O'Hare Intl for the best San Francisco - Chicago flight prices

You are more likely to see cheaper flights to Chicago from San Francisco when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $544 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from San Francisco for as low as $439 on momondo.

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

No. A direct flight is the cheapest option for a flight between San Francisco to Chicago.

As of March 2026, prices for San Francisco to Chicago flights are approximately 44% more expensive when compared to flights at the same time last year.

Historically, on average around 10% of flights between San Francisco and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 187 minutes.

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

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

According to our data, American Airlines have had the fewest delays on this route over the last 12 months, with about 10% of their flights experiencing any sort of delay.

The number of flights available between San Francisco and Chicago is 63 per day as of March 2026. The most frequent departure time is 10:00, with 51% of daily flights leaving at midday.

As of March 2026, there are 441 flights per week flying from San Francisco to Chicago. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.