Our data shows that the cheapest route for a return flight from Chicago to San Diego cost $320 and was between Chicago O'Hare Intl Airport (ORD) and San Diego (SAN). On average, the best prices are found if you fly from Chicago Midway Airport (MDW) to San Diego (SAN).

Find United Airlines cheap flights from Chicago to San Diego. Enjoy a Chicago to San Diego modern flight experience in premium cabins with Wi-Fi.

Each day, there are 2 nonstop flights that take off from Chicago Midway Airport and land in San Diego, with an average flight time of 4h 36m. The most common departure time is 8:00 am and most flights take off in the morning.

Flights from Chicago to San Diego. Use Google Flights to plan your next trip and find cheap one way or round trip flights from Chicago to San Diego. Find the best...

Finding the right flight to San Diego from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit.

Are you searching for American Airlines flights from Chicago to San Diego? Find the best selections and fly in style.

Fly one-way from Chicago (Midway) to San Diego starting at $171. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

Cheap Flights from Chicago (CHI) to San Diego (SAN) start at $33 for one-way and $66 for round trip. Earn your airline miles on top of our rewards!

Cheap Flights from Chicago (MDW) to San Diego (SAN) start at $60 for one-way and $120 for round trip. Earn your airline miles on top of our rewards!

If you are looking for an easy and convenient flight from Chicago to San Diego, you will be glad to know that there are several direct departures per day. These are typically operated by either American Airlines or United Airlines.