Cheap flights from San Diego to Chicago from $149

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from San Diego, with most prices found around $251. If you are unable to visit Chicago Midway Airport during the month of December, then departing from San Diego during the month February is also very affordable. Most momondo users find prices during this month for around $264.

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from San Diego. The lowest ticket price found for a Wednesday departure recently was $377. 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 $541.

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 $354 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $447. 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 $335 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 $139 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.

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

As of July 2026, prices for San Diego to Chicago Midway Airport flights are approximately 111% more expensive when compared to flights at the same time last year.

As of July 2026, there are 2 flights per day flying from San Diego to Chicago Midway Airport. The most common time of day flights depart is 5:00PM, with 47% of flights taking off in the afternoon.

As of July 2026, there are 15 flights per week flying from San Diego to Chicago Midway Airport. The most common day of the week flights depart is Thu, with 33% of flights taking off on this day.