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!
Chicago (Midway), IL to San Diego, CA
departing on 1/5
one-way starting at*$164
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 43 travel days available.
|Departing from||Chicago Midway International Airport (MDW)|
|Arriving at||San Diego International Airport (SAN)|
|Average flight time||4 hours 30 minutes|
|3‡||Nonstop flights per day Monday through Friday|
|2‡||Nonstop flights on Saturday|
|3‡||Nonstop flights on Sunday|
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 12/1/2023 and 12/31/2023. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 12/1/2023 and 12/31/2023.
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.
Arrive 3 miles northwest of downtown San Diego to begin your Southern California adventure.
At Southwest, we know it takes more than great deals on San Diego airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from Chicago (Midway) to San Diego the best it can be. Learn more about the Southwest® travel experience before you book your flight from Chicago Midway International Airport to San Diego International Airport.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. When you search for your next flight to San Diego, know that you won’t be surprised at checkout. Low fares and no hidden fees. That's Transfarency®. And as always, two bags fly free®1. Want the latest news, information, and promotional offers from Southwest? Sign up to receive email from us. Book your flight today and know that you'll earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
3Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.
4Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our systems are updated. See full details here.
5Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
6Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
7Internet access for $8 per device from takeoff to landing. Price is subject to change. May not be available for the full duration of flight. In order to provide a top-notch Internet experience, we prohibit access to certain high-bandwidth applications and websites. We also prohibit access to certain obscene or offensive content.