Cheap flights from Chicago to San Diego from $139

If you are unable to visit San Diego during the month of January, then departing from Chicago during the month February is also very affordable. Most momondo users find prices during this month for around $245.

The cheapest day to depart from Chicago to San Diego is on a Thursday. Travelers who choose to depart for San Diego on a Thursday will often find tickets for as low as $317. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $356. These prices are subject to change though, so be sure to set up a Price Alert for flights to San Diego.

The cheapest time of day to fly to San Diego is in the evening when flights can be purchased for as low as $293. Flights at noon are often more expensive with an average ticket price of $356.

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

You are more likely to see cheaper flights to San Diego from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San Diego for around $295 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Diego from Chicago for as low as $245 on momondo.

There are 4 cabin classes available to choose from on Chicago to San Diego 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 35% on your flight if you consider stops on a Chicago to San Diego flight.

As of August 2026, prices for Chicago to San Diego flights are approximately 42% more expensive when compared to flights at the same time last year.

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

American Airlines, United Airlines and Alaska Airlines are the top three most popular airlines that fly to San Diego from Chicago according to our data. American Airlines is the first choice among our users, with 41% of people opting to fly with this airline when traveling to San Diego. Keep in mind that there are 8 different airlines that fly to San Diego on a routine basis, so you have a few additional options to choose from.

The number of flights available between Chicago and San Diego is 27 per day as of August 2026. The most frequent departure time is 4:00PM, with 45% of daily flights leaving in the evening.

191 flights are operational weekly from Chicago to San Diego as of August 2026. The most popular departure day for this route is Mon, with 30% of flights per week taking off on this day.