Southwest® flights from Chicago (O'Hare) to San Antonio from $115
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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
$73
Seen: 37 minutes ago
Chicago (Midway) (MDW)to
San Antonio (SAT)
Depart: 01/27/2026
One-way
Basic
From
$77
Seen: 4 minutes ago
Chicago (Midway) (MDW)to
San Antonio (SAT)
Depart: 01/13/2026
One-way
Basic
From
$91
Seen: 9 minutes ago
Chicago (Midway) (MDW)to
San Antonio (SAT)
Depart: 01/26/2026
One-way
Basic
From
$91
Seen: 5 minutes ago
Chicago (Midway) (MDW)to
San Antonio (SAT)
Depart: 02/28/2026
One-way
Choice
From
$93
Seen: 37 minutes ago
Chicago (Midway) (MDW)to
San Antonio (SAT)
Depart: 01/27/2026
One-way
Choice
From
$97
Seen: 4 minutes ago
Explore flights from Chicago (O'Hare) to San Antonio
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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 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.
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.