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Find low faresSouthwest® flights from Chicago (O'Hare) to San Antonio from $146
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1 Passenger
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Low fares from Chicago (O'Hare) to San Antonio
$
Chicago (Midway) (MDW)to
San Antonio (SAT)
Depart: 02/28/2026
One-way
Basic
From
$113
Seen: 12 hrs ago
Chicago (Midway) (MDW)to
San Antonio (SAT)
Depart: 03/28/2026
One-way
Basic
From
$123
Seen: 10 hrs ago
Chicago (Midway) (MDW)to
San Antonio (SAT)
Depart: 04/25/2026
One-way
Basic
From
$123
Seen: 9 hrs ago
Chicago (Midway) (MDW)to
San Antonio (SAT)
Depart: 03/21/2026
One-way
Basic
From
$123
Seen: 2 hrs ago
Chicago (Midway) (MDW)to
San Antonio (SAT)
Depart: 03/28/2026
One-way
Choice
From
$137
Seen: 10 hrs ago
Chicago (Midway) (MDW)to
San Antonio (SAT)
Depart: 04/25/2026
One-way
Choice
From
$137
Seen: 9 hrs ago
Explore flights from Chicago (O'Hare) to San Antonio
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Flight Details
Departing from:
O'Hare International Airport
Arriving at:
San Antonio International Airport
Distance:
1041 miles
Route Information
125† 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 Antonio
On the banks of its eponymous river, San Antonio combines traditional Spanish and Mexican style with modern-day amenities, making it a comfortable and unique destination. The first thing you’ll want to do is check out the famed River Walk. Stroll along the San Antonio River, stop for a meal, and do some shopping—window or otherwise. Or you could take it all in by taking a boat ride to enjoy unforgettable views of the River Walk and other nearby attractions.
San Antonio is a must-visit for history buffs. Remember the Alamo? Well, it’s in San Antonio. A popular part of American history, this fortress was the site of the Battle of the Alamo in 1836; today it’s a museum and a church. There’s even more to explore at San Antonio Missions National Historic Park. It’s home to four of the five Spanish missions in San Antonio: Mission Concepción, Mission San Jose, Mission San Juan, and Mission Espada. You’ll also find the Espada Aqueduct there. Built in 1745, it was used to irrigate 3,500 acres of land.
Questions we hear the most
There are 125 weekly flights from Chicago (O'Hare) to San Antonio on Southwest Airlines.
To find the lowest fares by day and time to fly Chicago (O'Hare) to San Antonio with Southwest, check out our Low Fare Calendar.
You can rent a car at San Antonio International Airport book yours with your flight.
Yes! Flights from Chicago (O'Hare) to San Antonio—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.