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Find low faresSouthwest® flights from Chicago (Midway) to San Antonio from $113
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1 Passenger
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today
Low fares from Chicago (Midway) to San Antonio
$
Chicago (Midway) (MDW)to
San Antonio (SAT)
Depart: 02/21/2026
One-way
Choice
From
$113
Seen: 4 hrs ago
Chicago (Midway) (MDW)to
San Antonio (SAT)
Depart: 02/28/2026
One-way
Basic
From
$113
Seen: 20 hrs ago
Chicago (Midway) (MDW)to
San Antonio (SAT)
Depart: 04/25/2026
One-way
Basic
From
$123
Seen: 18 hrs ago
Chicago (Midway) (MDW)to
San Antonio (SAT)
Depart: 03/28/2026
One-way
Basic
From
$123
Seen: 19 hrs ago
Chicago (Midway) (MDW)to
San Antonio (SAT)
Depart: 04/18/2026
One-way
Choice
From
$123
Seen: 44 minutes ago
Chicago (Midway) (MDW)to
San Antonio (SAT)
Depart: 04/18/2026
One-way
Basic
From
$123
Seen: 44 minutes ago
Explore flights from Chicago (Midway) to San Antonio
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Flight Details
Departing from:
Chicago Midway International Airport
Arriving at:
San Antonio International Airport
Average flight time:
2 hours 48 minutes
Distance:
1036 miles
Route Information
156† Weekly flights
- 2‡ Nonstop flights per day Monday through Friday
- 2‡ Nonstop flights on Saturday
- 2‡ 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.
Questions we hear the most
The average flight time from Chicago (Midway) to San Antonio is 2 hours 48 minutes.
There are 156 weekly flights from Chicago (Midway) to San Antonio on Southwest Airlines.
Yes, Southwest flies nonstop from Chicago (Midway) to San Antonio 2 times per day from Monday through Friday.
Yes, Southwest flies nonstop from Chicago (Midway) to San Antonio 2 times per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Chicago (Midway) 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 (Midway) 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.