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Take a break from the Windy City and head west to sunny San Diego! Southwest Airlines® has flights from Chicago Midway International Airport to San Diego International Airport that make booking your next getaway a breeze. Find your flight to San Diego with Southwest® and book with confidence. If your upcoming travel schedule is flexible, search for flights with our Low Fare Calendar and find the lowest fares we’ve got. Don't forget to check out Southwest Vacations® to find package deals on flights, hotels, rental cars, and more.
Find Chicago (Midway) to San Diego flights and book yours today!
Average Flight Time: 4 hours 10 minutes
Departing from: Chicago Midway International Airport (MDW)
Arriving at: San Diego International Airport (SAN)
Downtown San Diego is a quick drive, bus trip, or even bike ride from the airport, so you can head straight into the action after landing! San Diego is the oldest city in California and filled to the brim with cultural history and notable landmarks. Military history buffs will want to take a tour through the USS Midway Aircraft Carrier Museum, one of the United States military's largest ships. Those interested in religious history should pay a visit to Mission Basilica San Diego de Alcala, California’s first mission, which hosts a small museum. In downtown San Diego, a stroll through the historic Gaslamp Quarter makes for a lovely afternoon of exploring restored late-19th- and early 20th-century Victorian buildings.
When you need a break from the history lesson, take a plunge into the Pacific! San Diego is known for its sunny weather and has over 68 miles of beaches, making it a prime destination for surfers—professional and amateur alike. Rollerblade down the classic Southern Californian Mission Beach Boardwalk, take a dip at Coronado Beach, try snorkeling or scuba diving at La Jolla Shores, or simply enjoy a fresh fish taco (or two) under the palm trees.
San Diego’s natural wonders go beyond the beach! Visitors can enjoy a variety of hikes and scenic views all along the Pacific coast. Torrey Pines State Reserve boasts 1,750 acres of unspoiled land, including salt marshes and waterfowl refuges. It’s even home to the Torrey Pine, America’s rarest pine tree! A walk out to Point Loma rewards visitors with breathtaking views of the city, and the opportunity to tour the Old Point Loma Lighthouse. And locals will agree that the best way to end a day of hiking is by watching the sunset from the coastal bluffs at Sunset Cliffs Natural Park!
One child over 14 days and under two (2) years of age, not occupying a seat, may be carried free of charge when traveling with an adult (12 years of age or older). Learn more.
Customers flying with a pet are subject to a pet fare. To learn more about traveling with your furry friend, explore the Southwest Pet Policy.
Minors under the age of 18 are not permitted to fly unaccompanied on international flights or any itinerary that includes an international flight. Learn more.
Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.
Here at Southwest, we know that a memorable trip from Chicago to San Diego is made of more than just cheap flights from Midway to San Diego International Airport. That’s why we offer services and perks that make your travel experience as smooth as possible, from booking to boarding. Learn more about the Southwest Experience before you book your Chicago (Midway) to San Diego flight.
Flying with Southwest is simple and fun, no matter which of our exciting destinations you choose. And when you search for your next flight to San Diego, you know you won’t be hassled by hidden fees—we offer low fares and, as always, bags fly free1. That’s our Transfarency® promise. Enroll in our Click 'N Save® emails and stay up to date on our latest flight deals. Also interested in tours, activities, and more hidden gems? Explore Southwest Airlines® Experiences and earn Rapid Rewards® when you book.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.