$77 Cheap Flights from San Antonio (SAT) to Chicago (MDW)

View $77 flight on Tue, Jan 13, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at $77 for one-way flights and $164 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sun, Dec 21 - Wed, Dec 31
SAT
San Antonio
MDW
Chicago
$164 Roundtrip, found 3 hours ago
$164
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sun, Dec 21 from San Antonio to Chicago, returning Wed, Dec 31, priced at $164 found 3 hours ago
Frontier Airlines
Tue, Dec 30 - Wed, Dec 31
SAT
San Antonio
MDW
Chicago
$173 Roundtrip, found 20 hours ago
$173
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Tue, Dec 30 from San Antonio to Chicago, returning Wed, Dec 31, priced at $173 found 20 hours ago
Frontier Airlines
Mon, Feb 23 - Mon, Mar 2
SAT
San Antonio
MDW
Chicago
$182 Roundtrip, found 5 days ago
$182
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Feb 23 from San Antonio to Chicago, returning Mon, Mar 2, priced at $182 found 5 days ago
Frontier Airlines
Tue, Dec 30 - Wed, Dec 31
SAT
San Antonio
MDW
Chicago
$183 Roundtrip, found 5 hours ago
$183
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Dec 30 from San Antonio to Chicago, returning Wed, Dec 31, priced at $183 found 5 hours ago
Frontier Airlines
Mon, Mar 2 - Mon, Mar 9
SAT
San Antonio
MDW
Chicago
$192 Roundtrip, just found
$192
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Mar 2 from San Antonio to Chicago, returning Mon, Mar 9, priced at $192 just found
Southwest Airlines
Sat, Feb 21 - Wed, Feb 25
SAT
San Antonio
MDW
Chicago
$198 Roundtrip, found 1 hour ago
$198
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sat, Feb 21 from San Antonio to Chicago, returning Wed, Feb 25, priced at $198 found 1 hour ago
Frontier Airlines
Thu, Dec 11 - Wed, Dec 31
SAT
San Antonio
MDW
Chicago
$204 Roundtrip, found 6 hours ago
$204
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Thu, Dec 11 from San Antonio to Chicago, returning Wed, Dec 31, priced at $204 found 6 hours ago
Frontier Airlines
Wed, Dec 24 - Wed, Dec 31
SAT
San Antonio
MDW
Chicago
$208 Roundtrip, just found
$208
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Dec 24 from San Antonio to Chicago, returning Wed, Dec 31, priced at $208 just found
Southwest Airlines
Sat, Feb 21 - Wed, Feb 25
SAT
San Antonio
MDW
Chicago
$212 Roundtrip, found 1 hour ago
$212
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sat, Feb 21 from San Antonio to Chicago, returning Wed, Feb 25, priced at $212 found 1 hour ago
Delta
Sat, Feb 21 - Wed, Feb 25
SAT
San Antonio
MDW
Chicago
$235 Roundtrip, found 1 hour ago
$235
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Feb 21 from San Antonio to Chicago, returning Wed, Feb 25, priced at $235 found 1 hour ago

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

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

March is typically the cheapest month to fly

From $118 - $626 per traveler.

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $207
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $207
Flights from San Antonio (SAT) to Chicago (MDW)
Origin airport
San Antonio Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$164
Distance
1037 mi
Average flight time
3 hours 5 mins

San Antonio to Chicago Flights

The cheapest times to fly from San Antonio to Chicago

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 San Antonio to Chicago are during the month of December. You can find some of the cheapest flights from San Antonio to Chicago with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from San Antonio to Chicago: 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 San Antonio to Chicago

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 San Antonio to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $77 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 San Antonio to Chicago 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 San Antonio to Chicago 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 San Antonio Intl. Airport (SAT) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight from $77 or cheap return flight from $164 from San Antonio Intl. Airport (SAT) to Midway Intl. Airport (MDW) 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 San Antonio Intl. Airport (SAT) to Midway Intl. Airport (MDW)?
The cheapest month to fly from SAT to MDW is December, when there's less demand. Off-peak months are often when airlines offer better prices between these airports.
Which airlines fly direct from San Antonio Intl. Airport (SAT) to Midway Intl. Airport (MDW)?
Fly nonstop from San Antonio Intl. Airport (SAT) to Midway Intl. Airport (MDW) on a Southwest Airlines flight.
What is the cheapest airline that flies from San Antonio Intl. Airport (SAT) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare airlines and find the cheapest carrier that'll fly you from SAT to MDW. Then, sort your results by "Price (lowest to highest)" to snag a good deal.
How many flights per day from San Antonio Intl. Airport (SAT) to Midway Intl. Airport (MDW)?
On average, San Antonio Intl. Airport (SAT) only has 1 direct flight to Midway Intl. Airport (MDW) daily. For additional options, try Expedia's easy-to-use filters. Simply enter your details, then choose "1 Stop" or "2+ Stops" to find flights offering layovers.
What are the most popular departure times for flights from San Antonio Intl. Airport (SAT) to Midway Intl. Airport (MDW)?
Flights between SAT and MDW are their busiest at 6 AM. If you're after a more relaxed experience and possibly cheaper fares, choose a time outside the usual busy windows.
What day of the week has the most flights from SAT to MDW?
If you travel on a Friday, you'll get the biggest range of choices for flights from San Antonio Intl. Airport (SAT) to Midway Intl. Airport (MDW).
What is the earliest flight from San Antonio Intl. Airport (SAT) to Midway Intl. Airport (MDW)?
Catch the earliest flight at around 5:40AM UTC-6, heading out of San Antonio Intl. Airport (SAT). You'll be flying for roughly 2h 30m, reaching Midway Intl. Airport (MDW) at approximately 8:10AM UTC-6.
How long does it take to fly from San Antonio Intl. Airport (SAT) to Midway Intl. Airport (MDW)?
Flights from SAT to MDW have an average travel time of 2 hours and 32 minutes. The distance between the two is 1,050 mi.
What airline has the least delays from SAT to MDW?
With 81% of flights usually landing on schedule, Southwest Airlines has the best on-time performance for nonstop flights from San Antonio Intl. Airport (SAT) to Midway Intl. Airport (MDW). To monitor your flight status and receive notifications about any changes, simply head to the Expedia App.
What is the best time to fly from San Antonio Intl. Airport (SAT) to Midway Intl. Airport (MDW)?
To reach Midway Intl. Airport (MDW) without delays, pick a flight that leaves San Antonio Intl. Airport (SAT) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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 Chicago from San Antonio Intl. Airport (SAT)?
Board a direct flight from San Antonio Intl. Airport (SAT) to Chicago and land at O'Hare Intl. Airport (ORD). Another entry point into the city is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from San Antonio Intl. Airport (SAT) to Midway Intl. Airport (MDW) last-minute?
Holding off until right before your break to book your flight from SAT to MDW generally means paying more. While you may come across some last-minute offers, they're not always guaranteed. Allow some flexibility in your schedule to maximize your chances of snagging a bargain.
Is it cheaper to book a SAT to MDW flight and hotel package?
You'll generally save money by booking a SAT to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one place. After selecting your ideal flights and accommodations, you can add extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from San Antonio Intl. Airport (SAT) to Midway Intl. Airport (MDW)?
In most instances, you can cancel or modify your SAT to MDW flight. However, additional charges may apply, especially if you booked over 24 hours ago. Double-check your itinerary for the airline's fees and guidelines on flight changes, or if you need further information, head to our Customer Service portal.

Explore a world of travel with Expedia

*Available to One Key members.