$112 Cheap Flights from Chicago (MDW) to San Antonio (SAT)

View $112 flight on Thu, May 15, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to San Antonio International Airport (SAT)

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Find available prices by choosing your travel dates.

Cheap Flights from Chicago to San Antonio (MDW-SAT)

Prices were available within the past 7 days and start at $112 for one-way flights and $188 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, May 31 - Wed, Jun 4
MDW
Chicago
SAT
San Antonio
$188 Roundtrip, found 12 hours ago
$188
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Sat, May 31 from Chicago to San Antonio, returning Wed, Jun 4, priced at $188 found 12 hours ago
Frontier Airlines
Sun, Jun 1 - Wed, Jun 4
MDW
Chicago
SAT
San Antonio
$198 Roundtrip, found 12 hours ago
$198
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Sun, Jun 1 from Chicago to San Antonio, returning Wed, Jun 4, priced at $198 found 12 hours ago
Southwest Airlines
Thu, May 15 - Sun, May 18
MDW
Chicago
SAT
San Antonio
$216 Roundtrip, found 16 hours ago
$216
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Thu, May 15 from Chicago to San Antonio, returning Sun, May 18, priced at $216 found 16 hours ago
Frontier Airlines
Sat, Jun 7 - Mon, Jun 9
MDW
Chicago
SAT
San Antonio
$218 Roundtrip, found 8 hours ago
$218
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, Jun 7 from Chicago to San Antonio, returning Mon, Jun 9, priced at $218 found 8 hours ago
Frontier Airlines
Fri, Jun 6 - Mon, Jun 9
MDW
Chicago
SAT
San Antonio
$228 Roundtrip, just found
$228
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Jun 6 from Chicago to San Antonio, returning Mon, Jun 9, priced at $228 just found
Frontier Airlines
Thu, May 22 - Wed, May 28
MDW
Chicago
SAT
San Antonio
$230 Roundtrip, found 1 day ago
$230
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, May 22 from Chicago to San Antonio, returning Wed, May 28, priced at $230 found 1 day ago
Frontier Airlines
Sun, May 18 - Fri, May 23
MDW
Chicago
SAT
San Antonio
$240 Roundtrip, found 1 day ago
$240
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, May 18 from Chicago to San Antonio, returning Fri, May 23, priced at $240 found 1 day ago
Southwest Airlines
Tue, May 27 - Fri, May 30
MDW
Chicago
SAT
San Antonio
$241 Roundtrip, found 2 days ago
$241
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, May 27 from Chicago to San Antonio, returning Fri, May 30, priced at $241 found 2 days ago
Southwest Airlines
Thu, May 15 - Sun, May 18
MDW
Chicago
SAT
San Antonio
$246 Roundtrip, found 16 hours ago
$246
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Thu, May 15 from Chicago to San Antonio, returning Sun, May 18, priced at $246 found 16 hours ago
Delta
Wed, May 28 - Tue, Jun 3
MDW
Chicago
SAT
San Antonio
$307 Roundtrip, found 3 days ago
$307
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, May 28 from Chicago to San Antonio, returning Tue, Jun 3, priced at $307 found 3 days ago
Flights from Chicago (MDW) to San Antonio (SAT)
Origin airport
Midway Intl.
Destination airport
San Antonio Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$188
Distance
1037 mi

Chicago to San Antonio Flights

The cheapest times to fly from Chicago to San Antonio

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to San Antonio are during the month of May. You can find some of the cheapest flights from Chicago to San Antonio with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to San Antonio

Sunday is one of the best days to book for cheap flights from Chicago to San Antonio: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Chicago to San Antonio

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to San Antonio in 2025. You can also book with separate airlines for your outbound and return journeys, from $112 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to San Antonio flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to San Antonio airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to San Antonio Intl. Airport (SAT) cost?
Pick up cheap return flights starting at $297 from Midway Intl. Airport (MDW) to San Antonio Intl. Airport (SAT). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and United flight leaving MDW on May 11 2025 and touching down at SAT. The price was last updated on April 23 2025 and has not changed since.
What is the cheapest month to fly from MDW to SAT?
The cheapest flights from MDW to SAT are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to San Antonio Intl. Airport (SAT)?
When setting off from Midway Intl. Airport (MDW), you can take a nonstop flight to San Antonio Intl. Airport (SAT) with Southwest Airlines.
What is the cheapest airline that flies from MDW to SAT?
Jet off from MDW to SAT with Southwest Airlines. This airline currently offers the cheapest one-way fare for this route, starting from $144. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on May 27 2025. Prices were last updated on April 23 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to San Antonio Intl. Airport (SAT)?
On average, there is just 1 direct flight taking off from Midway Intl. Airport (MDW) to San Antonio Intl. Airport (SAT) each day. If this doesn’t fit your plans, check out flights with layovers. Simply filter your search on Expedia to include one or more stops to find a better alternative.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to San Antonio Intl. Airport (SAT)?
Flights between MDW and SAT are their busiest at 8 AM. If you’d like a more relaxed atmosphere and possibly cheaper fares, look for a time when demand is lower.
What day of the week has the most flights from MDW to SAT?
If you travel on a Friday, you’ll get the widest range of options for flights from Midway Intl. Airport (MDW) to San Antonio Intl. Airport (SAT).
What is the earliest flight from Midway Intl. Airport (MDW) to San Antonio Intl. Airport (SAT)?
Catch the earliest flight at around 8:25AM UTC-6, heading out of Midway Intl. Airport (MDW). You’ll be in the air for around 3h 5m, landing at San Antonio Intl. Airport (SAT) at approximately 11:30AM UTC-6.
How long does it take to fly from Midway Intl. Airport (MDW) to San Antonio Intl. Airport (SAT)?
Flights from MDW to SAT have an average travel time of 3 hours and 3 minutes. The distance between the two airports is 1,050 mi.
What airline has the least delays from MDW to SAT?
Southwest Airlines has the strongest track record for on-time direct flights from Midway Intl. Airport (MDW) to San Antonio Intl. Airport (SAT), with an on-time rating of 85%. Use the Expedia App to check your flight schedule before you jet off and get notified of any trip changes.
What is the best time to fly from Midway Intl. Airport (MDW) to San Antonio Intl. Airport (SAT)?
To avoid possible delays on the Midway Intl. Airport (MDW) to San Antonio Intl. Airport (SAT) route, travel before 3 PM. Later flights are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for San Antonio from Midway Intl. Airport (MDW)?
San Antonio Intl. Airport (SAT) is the only airport in San Antonio with direct flights from Midway Intl. Airport (MDW). Compare your options and discover cheap fares on Expedia.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to San Antonio Intl. Airport (SAT) last-minute?
Last-minute fares from MDW to SAT are generally more expensive. For the best rates, start searching for flights ahead of time. That being said, if your travel plans are flexible, you may land a cheap fare right before you leave.
Is it cheaper to book a MDW to SAT flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to SAT flight and hotel package with Expedia could result in significant savings. Better yet, having it all in one place takes the hassle out of travel planning. Just pick your flights and select from our extensive range of stays, then customize your trip with extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to San Antonio Intl. Airport (SAT)?
If you reserved your MDW to SAT flight within the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of fare you have, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you’d like more information.

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*Available to One Key members.