Cheap flights from San Diego to Chicago from $139

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from San Diego, with most prices found around $264. If you are unable to visit Chicago Midway Airport during the month of February, then departing from San Diego during the month January is also very affordable. Most momondo users find prices during this month for around $282.

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from San Diego. The lowest ticket price found for a Saturday departure recently was $385. 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 Diego because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $476.

Flying to Chicago Midway Airport from San Diego in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $386 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $526. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Chicago Midway Airport from San Diego when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $382 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 Diego for as low as $279 on momondo.

There is only 1 cabin class available to choose from on San Diego to Chicago Midway Airport 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 8% on your flight if you consider stops on a San Diego to Chicago Midway Airport flight.

As of November 2026, prices for San Diego to Chicago Midway Airport flights are approximately 58% more expensive when compared to flights at the same time last year.

As of November 2026, there are 2 flights per day flying from San Diego to Chicago Midway Airport. The most common time of day flights depart is 6:00AM, with 55% of flights taking off at noon.

As of November 2026, there are 16 flights per week flying from San Diego to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 19% of flights taking off on this day.