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Find low faresSouthwest® flights from Chicago (Midway) to San Diego from $66
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Low fares from Chicago (Midway) to San Diego
$
Chicago (Midway) (MDW)to
San Diego (SAN)
Depart: 02/28/2026
One-way
Basic
From
$66
Seen: 23 hrs ago
Chicago (Midway) (MDW)to
San Diego (SAN)
Depart: 03/07/2026
One-way
Basic
From
$66
Seen: 22 hrs ago
Chicago (Midway) (MDW)to
San Diego (SAN)
Depart: 04/18/2026
One-way
Basic
From
$66
Seen: 12 hrs ago
Chicago (Midway) (MDW)to
San Diego (SAN)
Depart: 05/02/2026
One-way
Basic
From
$66
Seen: 3 hrs ago
Chicago (Midway) (MDW)to
San Diego (SAN)
Depart: 02/21/2026
One-way
Basic
From
$66
Seen: 21 hrs ago
Chicago (Midway) (MDW)to
San Diego (SAN)
Depart: 02/24/2026
One-way
Basic
From
$79
Seen: 11 hrs ago
Explore flights from Chicago (Midway) to San Diego
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Flight Details
Departing from:
Chicago Midway International Airport
Arriving at:
San Diego International Airport
Average flight time:
4 hours 19 minutes
Distance:
1728 miles
Route Information
156† Weekly flights
- 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 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.
‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.
Explore San Diego
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.
Questions we hear the most
The average flight time from Chicago (Midway) to San Diego is 4 hours 19 minutes.
There are 156 weekly flights from Chicago (Midway) to San Diego on Southwest Airlines.
Yes, Southwest flies nonstop from Chicago (Midway) to San Diego 3 times per day from Monday through Friday.
Yes, Southwest flies nonstop from Chicago (Midway) to San Diego 2 times per day on Saturdays and 3 times per day on Sundays.
To find the lowest fares by day and time to fly Chicago (Midway) to San Diego with Southwest, check out our Low Fare Calendar.
You can rent a car at San Diego International Airport book yours with your flight.
Yes! Flights from Chicago (Midway) to San Diego—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Check the status of your upcoming Southwest flight.
Check out the Southwest Airlines® Help Center for answers about everything Southwest.