Cheap flights from San Francisco to Chicago from $184

If you don’t want to visit Chicago in September, then you should wait until July to fly from San Francisco, when ticket prices are also cheap, with an average price of $416.

Our data shows that the cheapest San Francisco to Chicago flights are usually those with departure times in the morning. Our users have found flights to Chicago in the morning for as low as $665. Flights in the evening are often more expensive, with an average ticket price of $829.

Fly from San Francisco to Chicago Midway 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 $543 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 $450 on momondo.

You could potentially save up to 29% on your flight if you consider stops on a San Francisco to Chicago flight.

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 185 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, United 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 71 per day as of May 2026. The most frequent departure time is 10:00, with 35% of daily flights leaving at midday.

As of May 2026, there are 503 flights per week flying from San Francisco to Chicago. The most common day of the week flights depart is Wed, with 18% of flights taking off on this day.