Cheap Flight Tickets from Chicago (MDW) to San Antonio (SAT), Starting at $296

Good to Know: Cheapest and Fastest MDW - SAT Flights

Useful information for finding best airline tickets from Chicago Midway International to San Antonio International on your next trip.

Cheapest Round Trip Flight

$296

WN Southwest Airlines • 1 stop • 6h 55m

Oct 12 – Oct 19

The cheapest round trip flight from Chicago to San Antonio (MDW-SAT-MDW) is currently $296

🔍 Search Flights

Cheapest Direct Flight

$296

WN Southwest Airlines • nonstop • 4h 5m

Oct 12

The cheapest nonstop flight from Chicago to San Antonio (MDW-SAT) is currently $296

🔍 Search Flights

Fastest Flight

4h 5m

The fastest nonstop flight from Chicago to San Antonio (MDW-SAT) takes 4h 5m

Top Airlines Flying from Chicago to San Antonio

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

Latest Flight Deals from Chicago (MDW) to San Antonio (SAT)

Compare and book low fare round-trip air tickets from Chicago to San Antonio. Ideal for travelers with confirmed return itineraries.

Oct 12 - Oct 19, Economy
WN
Chicago → San Antonio
6h 55m
3:50 PM - 8:05 PM • 1 stop
WN
Chicago → San Antonio
4h
2:35 PM - 5:15 PM • nonstop
$296
Southwest Airlines
Oct 12 - Oct 19, Economy
WN
Chicago → San Antonio
10h 5m
5:50 PM - 11:55 PM • 1 stop
WN
Chicago → San Antonio
4h
9:20 AM - 12:00 PM • nonstop
$296
Southwest Airlines
Oct 12 - Oct 19, Economy
WN
Chicago → San Antonio
4h 5m
9:45 AM - 12:30 PM • nonstop
WN
Chicago → San Antonio
4h
2:35 PM - 5:15 PM • nonstop
$296
Southwest Airlines
Oct 12 - Oct 19, Economy
WN
Chicago → San Antonio
10h 25m
9:40 AM - 4:05 PM • 1 stop
WN
Chicago → San Antonio
4h
9:20 AM - 12:00 PM • nonstop
$296
Southwest Airlines
Oct 12 - Oct 19, Economy
WN
Chicago → San Antonio
8h 55m
9:40 AM - 3:15 PM • 1 stop
WN
Chicago → San Antonio
4h
2:35 PM - 5:15 PM • nonstop
$296
Southwest Airlines
Oct 12 - Oct 19, Economy
DL
Chicago → San Antonio
12h 4m
5:09 PM - 12:33 AM • 1 stop
DL
Chicago → San Antonio
10h 24m
5:30 AM - 11:54 AM • 1 stop
$339
Delta Airlines

Fly from Chicago to San Antonio with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to San Antonio? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Chicago to San Antonio Flights

What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from MDW to SAT?
The most popular airline flying from Chicago to San Antonio are
Can I fly from MDW to SAT non-stop?
Yes, you can fly MDW to SAT non-stop on
Which airlines fly nonstop between Chicago and San Antonio?
The non-stop flights between Chicago and San Antonio are .
What’s the earliest departure time from MDW to SAT Airport?
The earliest flight leaves MDW at 9:40 am and lands in SAT - San Antonio International
What are the airports in San Antonio?
SAT
Can I make changes to my Chicago to San Antonio flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from MDW to SAT?
Read the fare rules of the Chicago to San Antonio air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Chicago and San Antonio?
operate flights between Chicago and San Antonio
How long does a flight from Chicago to San Antonio take?
It takes approximately 3 hour to fly non-stop from MDW to SAT, which is 1035.99 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to San Antonio (SAT) ?
In the past couple of days, the cheapest tickets to SAT from MDW were found on WN : USD 296
Do I need a passport to fly between MDW and SAT?
No
What’s the latest departure time from MDW to SAT ?
The last flight leaves MDW at 9:20 pm

Chicago (MDW) to San Antonio (SAT): Airport Information

Origin Airport Chicago Midway International , Chicago, US
Destination Airport San Antonio International , San Antonio, US
Distance 1036 miles

More Flight Options for Chicago (MDW) and San Antonio (SAT)

Why Fareleaders for MDW to SAT Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Chicago to San Antonio flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on MDW to SAT flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Chicago to San Antonio flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Chicago (MDW) to San Antonio (SAT)
Terms and Conditions*