Cheap flights from San Francisco Bay Area to Chicago from $80

The month of September is, on average, the cheapest month to fly to Chicago from San Francisco Bay Area, 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 Bay Area to Chicago during April average around $325.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $403. 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 Bay Area to Chicago for around $500.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from San Francisco Bay Area to Chicago during this time can be as low as $415. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $456.

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

You are more likely to see cheaper flights to Chicago from San Francisco Bay Area when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $381 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 Bay Area for as low as $307 on momondo.

There are 4 cabin classes available to choose from on San Francisco Bay Area to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Southwest, Delta, and United Airlines are the most popular carriers operating from San Francisco Bay Area to Chicago

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from San Francisco Bay Area according to our data. United Airlines is the first choice among our users, with 47% 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.

As of March 2026, 64 flights take off from San Francisco Bay Area and land in Chicago each day. The most common flight departure time for this route is 10:00AM, with 49% of daily flights taking off at noon.

As of March 2026, there are 449 flights per week flying from San Francisco Bay Area to Chicago. The most common day of the week flights depart is Sun, with 21% of flights taking off on this day.