$153 Find Cheap Flights from Chicago Midway Airport to San Diego - Compare and Save

If your flying dates are flexible, you should consider flying to San Diego on a Sunday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Chicago Midway Airport to San Diego. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals.

The cheapest month for flights from Chicago Midway Airport to San Diego is February, where tickets cost $207 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is $451 and $430 respectively.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $357 on average.

To get a below average price on the flight from Chicago Midway Airport to San Diego, you should book around 4 weeks before departure, which saves you about 47% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

In the past 5 days, the cheapest round-trip tickets from Chicago Midway Airport to San Diego were found on Southwest ($267) and Delta ($269).

There is just one airline that flies from Chicago Midway Airport to San Diego direct and that is Southwest. The best round-trip deal found from Southwest for the route is $177.

Phoenix (PHX) is the top choice – 50% of KAYAK users who clicked on 1-stop flights from Chicago Midway Airport to San Diego picked an itinerary connecting there.

Flights via Atlanta (ATL) offer the most affordable fares, with an average round-trip price of $186.

Consider flying via Phoenix (PHX) for the shortest journey. The average one-way travel time for flights connecting there is 6h 18m.

If you prefer a quick connection, Phoenix (PHX) often has the shortest layovers from Chicago Midway Airport to San Diego, with an average of 1h 12m.

There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Each day, there are between 3 and 4 nonstop flights that take off from Chicago Midway Airport and land in San Diego, with an average flight time of 4h 08m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 24 flights. The most frequent day of departure is Monday, when 17% of all weekly flights depart. The fewest flights depart on a Tuesday.