Southwest® flights from Chicago-Midway to San Diego from $137

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.