Cheap flights from San Diego to Chicago from $121

The month of February is, on average, the cheapest month to fly to Chicago from San Diego, with most prices found around $253. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from San Diego to Chicago during January average around $262.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $410. 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 Diego to Chicago for around $577.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from San Diego to Chicago during this time can be as low as $364. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $481.

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

You are more likely to see cheaper flights to Chicago from San Diego when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $325 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from San Diego for as low as $273 on momondo.

There are 4 cabin classes available to choose from on San Diego to Chicago 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 5% on your flight if you consider stops on a San Diego to Chicago flight.

As of October 2026, prices for San Diego to Chicago flights are approximately 57% more expensive when compared to flights at the same time last year.

Southwest, Alaska Airlines, and Frontier are the most popular carriers operating from San Diego to Chicago

American Airlines, United Airlines and Alaska Airlines are the top three most popular airlines that fly to Chicago from San Diego 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 Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 9% of flights between San Diego and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 192 minutes.

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 6% of their flights experiencing any sort of delay.

Denver (DEN) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Flights via Phoenix (PHX) offer the lowest average round-trip price of $109.

Flights connecting via Phoenix (PHX) have the shortest average one-way travel time: 6h 08m.

Phoenix (PHX) has the shortest average layover time for this route: 3h 06m.

52 flights are operational daily from San Diego to Chicago as of October 2026. The most popular departure time for this route is 10:00AM, with 59% of flights per day taking off at noon.

The number of flights available between San Diego and Chicago is 364 per week as of October 2026. The most frequent departure day is Fri, with 16% of weekly flights leaving on this day.