Cheap flights from Chicago Midway Airport to San Diego from $139

If you are unable to visit San Diego during the month of February, then departing from Chicago Midway Airport during the month May is also very affordable. Most momondo users find prices during this month for around $291.

The cheapest day to depart from Chicago Midway Airport 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 $346. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $389. 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 $327. Flights at noon are often more expensive with an average ticket price of $363.

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

You are more likely to see cheaper flights to San Diego from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to San Diego for around $356 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 Midway Airport for as low as $272 on momondo.

There is only 1 cabin class available to choose from on Chicago Midway Airport to San Diego flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to San Diego.

As of November 2026, prices for Chicago Midway Airport to San Diego flights are approximately 203% more expensive when compared to flights at the same time last year.

2 flights are operational daily from Chicago Midway Airport to San Diego as of November 2026. The most popular departure time for this route is 10:00AM, with 63% of flights per day taking off at noon.

As of November 2026, there are 19 flights per week flying from Chicago Midway Airport to San Diego. The most common day of the week flights depart is Fri, with 37% of flights taking off on this day.