$66 Cheap Flights from Chicago (MDW) to San Antonio (SAT)

View $66 flight on Mon, Nov 17, 2025Opens in a new window

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

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Today's featured flight deals from Chicago Midway Airport (MDW) to San Antonio International Airport (SAT)

Nonstop
Carry-on included
Lower price than typical

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

Prices were available within the past 7 days and start at $66 for one-way flights and $124 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Mon, Dec 8 - Sun, Dec 14
MDW
Chicago
SAT
San Antonio
$124 Roundtrip, found 6 hours ago
$124
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Mon, Dec 8 from Chicago to San Antonio, returning Sun, Dec 14, priced at $124 found 6 hours ago
Frontier Airlines
Mon, Dec 8 - Sun, Dec 14
MDW
Chicago
SAT
San Antonio
$128 Roundtrip, found 6 hours ago
$128
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Mon, Dec 8 from Chicago to San Antonio, returning Sun, Dec 14, priced at $128 found 6 hours ago
Frontier Airlines
Mon, Jan 12 - Sun, Jan 18
MDW
Chicago
SAT
San Antonio
$134 Roundtrip, found 3 days ago
$134
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Jan 12 from Chicago to San Antonio, returning Sun, Jan 18, priced at $134 found 3 days ago
Frontier Airlines
Fri, Jan 9 - Sun, Jan 18
MDW
Chicago
SAT
San Antonio
$138 Roundtrip, found 2 days ago
$138
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Jan 9 from Chicago to San Antonio, returning Sun, Jan 18, priced at $138 found 2 days ago
Frontier Airlines
Fri, Jan 9 - Sun, Jan 11
MDW
Chicago
SAT
San Antonio
$148 Roundtrip, found 4 hours ago
$148
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Fri, Jan 9 from Chicago to San Antonio, returning Sun, Jan 11, priced at $148 found 4 hours ago
Frontier Airlines
Fri, Jan 23 - Mon, Jan 26
MDW
Chicago
SAT
San Antonio
$152 Roundtrip, found 4 hours ago
$152
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Fri, Jan 23 from Chicago to San Antonio, returning Mon, Jan 26, priced at $152 found 4 hours ago
Frontier Airlines
Thu, Jan 8 - Fri, Jan 9
MDW
Chicago
SAT
San Antonio
$154 Roundtrip, found 3 days ago
$154
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Jan 8 from Chicago to San Antonio, returning Fri, Jan 9, priced at $154 found 3 days ago
Frontier Airlines
Fri, Dec 5 - Thu, Dec 11
MDW
Chicago
SAT
San Antonio
$173 Roundtrip, found 5 days ago
$173
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Dec 5 from Chicago to San Antonio, returning Thu, Dec 11, priced at $173 found 5 days ago
Southwest Airlines
Thu, Jan 8 - Sat, Jan 10
MDW
Chicago
SAT
San Antonio
$240 Roundtrip, found 3 days ago
$240
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Jan 8 from Chicago to San Antonio, returning Sat, Jan 10, priced at $240 found 3 days ago
Delta
Thu, Dec 25 - Thu, Jan 1
MDW
Chicago
SAT
San Antonio
$327 Roundtrip, found 4 days ago
$327
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Dec 25 from Chicago to San Antonio, returning Thu, Jan 1, priced at $327 found 4 days ago

Find the cheapest month to fly from Chicago (MDW) to San Antonio (SAT)

February is typically the cheapest month to fly

From $128 - $475 per traveler.

Alternative airports near San Antonio

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to San Antonio Intl. SAT. Cheapest and Closest option available. Average driving time to city center is 11 minutes. Flights from $533
SAT
San Antonio Intl.
CheapestClosest
Average driving time to city center11 min
Flights from $533
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
$124
Distance
1037 mi
Average flight time
3 hours 18 mins

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 December. 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 $66 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?
Secure a cheap one-way flight from $66 or cheap return flight from $124 from Midway Intl. Airport (MDW) to San Antonio Intl. Airport (SAT) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to San Antonio Intl. Airport (SAT)?
Flying in December can help you save, as it's the cheapest month for flights between MDW and SAT. You'll typically find the lowest fares during off-peak months.
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 Midway Intl. Airport (MDW) to San Antonio Intl. Airport (SAT)?
Expedia's filter tool lets you easily compare different airlines, travel time and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find the carrier with the cheapest MDW to SAT flight.
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.