Cheap flights from San Francisco to Chicago from $111

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from San Francisco, with most prices found around $225. If you are unable to visit Chicago Midway Airport during the month of January, then departing from San Francisco during the month August is also very affordable. Most momondo users find prices during this month for around $289.

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from San Francisco. The lowest ticket price found for a Wednesday 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. On the other hand, Sunday is the most expensive day to depart from San Francisco because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $484.

Flying to Chicago Midway Airport from San Francisco in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $330 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $631. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from San Francisco to Chicago Midway for the best San Francisco - Chicago Midway flight prices

You are more likely to see cheaper flights to Chicago Midway Airport from San Francisco when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $361 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from San Francisco for as low as $262 on momondo.

There is only 1 cabin class available to choose from on San Francisco to Chicago Midway 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 18% on your flight if you consider stops on a San Francisco to Chicago Midway Airport flight.

Southwest and Delta are the most popular carriers operating from San Francisco to Chicago Midway

Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from San Francisco according to our data. Southwest is the first choice among our users, with 79% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 4 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

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.

2 flights are operational daily from San Francisco to Chicago Midway Airport as of March 2026. The most popular departure time for this route is 11:00PM, with 63% of flights per day taking off in the evening.

As of March 2026, 14 flights take off from San Francisco and land in Chicago Midway Airport each week. The most common flight departure day for this route is Tue, with 21% of weekly flights taking off on this day.