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Find low faresSouthwest® flights from Chicago (O'Hare) to San Diego from $84
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1 Passenger
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Low fares from Chicago (O'Hare) 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: 04/18/2026
One-way
Basic
From
$66
Seen: 11 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: 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: 03/10/2026
One-way
Basic
From
$79
Seen: 9 hrs ago
Explore flights from Chicago (O'Hare) to San Diego
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Flight Details
Departing from:
O'Hare International Airport
Arriving at:
San Diego International Airport
Distance:
1723 miles
Route Information
147† Weekly flights
† 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
San Diego has deep roots in aviation. While you’ll deplane at San Diego International Airport, this single-runway portal to the skies was originally named for Charles Lindbergh. Lindbergh tested his San Diego-built Spirit of St. Louis before his famous 1927 flight at the nearby Dutch Flats, inspiring the city to build the airport and invite more Americans to take to the air. When you deplane—or on your way home after your stay—consider swinging by Terminal 2 to see a recreation of Lindy’s famous plane.
You didn’t come to San Diego to explore the airport, of course! If your arrival marks your first visit to California, you can appreciate the city’s Birthplace of California moniker—Europeans first landed in San Diego Bay in 1542. Back then, it was claimed for Spain; this influence still echoes in the architecture of the city. Sightseers interested in exploring can’t-miss neighborhoods or landmarks can take a walking tour and let a local show them the way.
Questions we hear the most
There are 147 weekly flights from Chicago (O'Hare) to San Diego on Southwest Airlines.
To find the lowest fares by day and time to fly Chicago (O'Hare) 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 (O'Hare) 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.