Southwest® flights from Chicago (O'Hare) to San Diego from $67
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Low fares from Chicago (O'Hare) to San Diego
$
Chicago (Midway) (MDW)to
San Diego (SAN)
Depart: 02/18/2026
One-way
Basic
From
$55
Seen: 1 hour ago
Chicago (Midway) (MDW)to
San Diego (SAN)
Depart: 03/04/2026
One-way
Basic
From
$55
Seen: 1 hour ago
Chicago (Midway) (MDW)to
San Diego (SAN)
Depart: 01/07/2026
One-way
Basic
From
$62
Seen: 6 minutes ago
Chicago (Midway) (MDW)to
San Diego (SAN)
Depart: 03/04/2026
One-way
Choice
From
$75
Seen: 1 hour ago
Chicago (Midway) (MDW)to
San Diego (SAN)
Depart: 02/18/2026
One-way
Choice
From
$75
Seen: 1 hour ago
Chicago (Midway) (MDW)to
San Diego (SAN)
Depart: 01/12/2026
One-way
Basic
From
$77
Seen: 47 minutes ago
Explore flights from Chicago (O'Hare) to San Diego
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Travel tips for your next Southwest flight
How to board the plane earlier on open seating flights departing on or before January 26, 2026:
Southwest seats are first come, first served based on check-in order. But there are ways to board the plane earlier!
- Purchase EarlyBird Check-In®1 for automatic check-in and a better boarding position.
- Purchase Upgraded Boarding2 to get an A1-A15 boarding position (depending on availability).
- Purchase a Business Select® fare or upgrade to Business Select to get a guaranteed A1-A15 boarding position.
Enjoy movies, sips, and snacks during your flight.
Take advantage of inflight entertainment with free movies4, free live TV5, free texting6, and $8 inflight Internet7.
We also offer free sodas, coffee, and snacks8—learn more about the inflight food and beverage experience.
Make the most of our Rapid Rewards® Program.
Rapid Rewards Members can redeem their points for flights, hotel stays, rental cars, gift cards, and more. And your points never expire!
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.
Explore Flights from Other Popular Origins
Popular Flights from Chicago (O'Hare)
1EarlyBird Check-In® pricing starts at $15 one-way, and is subject to availability. Pricing may vary based on the popularity and length of each (one-way) flight. Please see optional travel charges for more details.
2Upgraded boarding prices and benefits are per eligible segment. Flights must be within 24 hours of departure to be eligible for upgraded boarding.
3Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
4Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
5Texting only allows access to iMessage and WhatsApp (which must be downloaded and activated before connecting to SouthwestWiFi).
6Internet 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.
7Flights traveling 175 miles or less will have only water available. Complimentary snacks are served on flights over 175 miles. If you’re flying between Hawaii and the continental U.S., you’ll have even more snacks to choose from.