Cheap Flights from Chicago to San Diego in 2019

Flight information Chicago to San Diego

Cheapest roundtrip price last month


Non-stop airlines


Flights per week


Average flight time, total distance 1702 miles

4h 9min

Most popular airline last month


San Diego International and McClellan – Palomar

2 airports

Explore San Diego

San Diego Hotels

When you travel from the art-deco skyscrapers of Chicago to the Spanish-style homes of San Diego, you’re covering more than 1,700 miles right across the middle of America. A direct flight will get you there with just a little over four hours spent in the air.


If you’re planning on flying from Chicago O’Hare (ORD) to San Diego’s Lindbergh Field (SAN) you can choose between American and United Airlines, which both offer several daily nonstop flights on the route. For those who prefer to leave from Chicago Midway (MDW), Southwest also offers a full direct schedule.


Making your way to Chicago’s airports

Chicago O’Hare is one of the busiest airports in the world by passenger traffic. Navigating your way through the crowds and the four huge terminals can be a challenge, but the airport’s high-speed people mover helps. You’ll still probably want to arrive two hours before even a domestic flight to give yourself a generous cushion.


The good news is that the excellent public transportation to O’Hare will let you forget about parking woes. The CTA Blue Line train runs every 15 minutes between the Loop and the airport, and the trip only takes about half an hour. It’s available 24/7, too.


In contrast, Chicago Midway is simplicity itself, with only one terminal, split into three concourses. Public transit is also a good option for this airport. Catch the CTA Orange Line, which will bring you from the Loop to Midway Airport in about 25 minutes. Remember that there’s a tunnel at the airport end, which means you’ll need to walk for 10-15 minutes before you reach the terminal.


Arriving in San Diego

If you want a full-on introduction to San Diego beach culture, plan a trip to Mission Beach. It can be crowded, but the collective fun and relaxation of thousands of people enjoying the coastline is contagious.


If you’re looking for something a little more peaceful, try hanging out with the sea lions at La Jolla cove. (The protected waters are also teaming with marine life, making it a great destination for snorkeling.)


Sunshine is one of the great natural resources of this part of the world, but it you want to enjoy the best of it, you might want to stay away during May and June, which can be quite overcast. After all that vitamin D, you’ll probably appreciate a cold one: the San Diego Craft Brewery offers some of the best microbrews in the world.


Don’t pay too much for your tickets from Chicago to San Diego. With Skyscanner’s free airfare comparison tool you can make sure you’ve found the cheapest flights out there.


Prices shown on this page are estimated lowest prices only. Found in the last 45 days.