Cheap flights from San Francisco to Chicago from $109

The month of September is, on average, the cheapest month to fly to Chicago from San Francisco, with most prices found around $291. If you’re not able to fly to Chicago in September, then April is your next best option. Flight prices from San Francisco to Chicago during April average around $323.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $404. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from San Francisco to Chicago for around $496.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from San Francisco to Chicago during this time can be as low as $409. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $456.

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 $379 when searching weeks out. 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 $297 on momondo.

There are 4 cabin classes 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.

You could potentially save up to 13% on your flight if you consider stops on a San Francisco to Chicago flight.

As of February 2026, prices for San Francisco to Chicago flights are approximately 26% more expensive when compared to flights at the same time last year.

Southwest and United Airlines are the most popular carriers operating from San Francisco to Chicago

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from San Francisco according to our data. United Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 9 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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 186 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening 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. Sunday has historically seen more delays on average compared to the rest of the week.

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

Orlando (MCO) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Flights via Minneapolis (MSP) offer the lowest average round-trip price of $261.

Flights connecting via Minneapolis (MSP) have the shortest average one-way travel time: 6h 15m.

Minneapolis (MSP) has the shortest average layover time for this route: 1h 00m.

54 flights are operational daily from San Francisco to Chicago as of February 2026. The most popular departure time for this route is 6:00AM, with 52% of flights per day taking off at noon.

The number of flights available between San Francisco and Chicago is 380 per week as of February 2026. The most frequent departure day is Mon, with 18% of weekly flights leaving on this day.