Cheap flights from Chicago to San Diego from $105

If you are unable to visit San Diego during the month of February, then departing from Chicago during the month January is also very affordable. Most momondo users find prices during this month for around $258.

The cheapest day to depart from Chicago to San Diego is on a Saturday. Travelers who choose to depart for San Diego on a Saturday will often find tickets for as low as $279. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $336. 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 at noon when flights can be purchased for as low as $270. Flights in the afternoon are often more expensive with an average ticket price of $311.

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 $277 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 $243 on momondo.

You could potentially save up to 12% on your flight if you consider stops on a Chicago to San Diego flight.

As of May 2026, prices for Chicago to San Diego flights are approximately 49% more expensive when compared to flights at the same time last year.

Alaska Airlines, Delta, and Southwest 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 44% of people opting to fly with this airline when traveling to San Diego. Keep in mind that there are 9 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 40 per day as of May 2026. The most frequent departure time is 6:00PM, with 54% of daily flights leaving in the evening.

284 flights are operational weekly from Chicago to San Diego as of May 2026. The most popular departure day for this route is Sun, with 17% of flights per week taking off on this day.