HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
San Antonio

$111+ Cheap flights from Midway (MDW) to San Antonio (SAT)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAT
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to San Antonio with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Midway to San Antonio

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San Antonio (SAT). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 28, 2025.

Round-trip from

$224
(Cheapflightsfares)

One-way from

$111
(Trip.com)

Popular in

March

Cheapest in

August

Average price

$317

Good round-trip deal

$235 or less

Good one-way deal

$213 or less
From Chicago Midway to San Antonio
Search Deals
One-way flight from Chicago Midway to San Antonio
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to San Antonio.
Search Deals
Price to beat on a one-way flight from Chicago Midway to San Antonio.
Search Deals

Find flight deals from Midway to San Antonio

Cheapest flights from Midway to San Antonio
Explore the most affordable flight options available from Midway to San Antonio. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 28, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/248:39 amMDW - SAT
1 stop6h 46mFrontier
Mon 10/275:35 pmSAT - MDW
1 stop5h 50mFrontier
Deal found 7/26$224
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/125:35 pmMDW - SAT
1 stop4h 15mSouthwest
Tue 11/186:40 amSAT - MDW
Nonstop2h 35mSouthwest
Deal found 7/27$241
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/304:25 pmMDW - SAT
1 stop7h 32mDelta
Tue 9/25:10 amSAT - MDW
1 stop7h 18mDelta
Deal found 7/28$255

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to San Antonio that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 28, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to San Antonio that are best for you.

Fly from

Midway

Fly to

San Antonio

Route

Depart

Return

Price

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Fri 10/24

8:39 am-3:25 pm

1 stop6h 46m

San Antonio

Mon 10/27

5:35 pm-11:25 pm

1 stop5h 50m

$224

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Thu 9/25

7:40 am-10:20 am

Nonstop2h 40m

San Antonio

Tue 9/30

11:00 am-5:15 pm

2 stops6h 15m

$250

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sat 8/30

4:25 pm-11:57 pm

1 stop7h 32m

San Antonio

Tue 9/2

5:10 am-12:28 pm

1 stop7h 18m

$255

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Mon 9/15

6:20 am-4:30 pm

1 stop10h 10m

$111

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 8/27

5:10 pm-7:50 pm

Nonstop2h 40m

$118

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sat 9/6

4:25 pm-11:57 pm

1 stop7h 32m

$128

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Mon 10/20

12:08 pm-4:55 am

2 stops16h 47m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

The best insider tips for Chicago Midway Airport to San Antonio flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to San Antonio trip
Airports
MDW

Use the Orange Line train for a quick, affordable trip to MDW, taking less than 30 minutes from downtown Chicago.

Read more about MDWby Ramsey Qubein
SAT

For a quick trip to downtown San Antonio, use Route 5 bus, taking about 30 minutes from SAT.

Read more about SATby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW and SAT

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Best time to book a flight from Midway to San Antonio

Have a flexible travel schedule? Discover the best time to fly to San Antonio from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to San Antonio

What is the cheapest month to book a flight from Chicago Midway Airport to San Antonio?

Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to San Antonio (average of $295). Flying from Chicago Midway Airport to San Antonio in March is currently the most expensive (average of $376). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to SAT?

Find hourly flight availability from Midway to San Antonio. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 28, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 11% on flights from Chicago Midway Airport to San Antonio by exploring options for tickets in the afternoon.

Reviews of airlines servicing San Antonio

Get insights into the airlines that provide service to San Antonio. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Antonio. Reviews last updated July 28, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Frontier from Chicago Midway Airport to San Antonio. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,975 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
5.9
Fair
3,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Midway to San Antonio. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to San Antonio from Chicago Midway?

    San Antonio (SAT), located 7.6 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to San Antonio. 2 airlines have flights to San Antonio from Chicago Midway on a regular basis. Booking flights from Chicago Midway to San Antonio should not be difficult; the airport handles an average of 1 inbound flight from Chicago Midway per day.

  • What are the cheapest airlines flying from Chicago Midway Airport to San Antonio round-trip?

    Flying on Frontier is currently your cheapest option to San Antonio, with prices starting at $224. Additional round-trip tickets that might be worth considering are offered by Southwest and Delta, with the lowest prices starting at $250 and $255, respectively. You may be able to fly from Chicago Midway Airport to San Antonio for 39% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Chicago Midway Airport to San Antonio one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $111. Southwest flights start at $118 while deals on Delta start at $128 one-way.

  • What are the cheapest flights from Chicago Midway Airport to San Antonio?

    The cheapest flight price from Chicago Midway Airport to San Antonio is $117. On average you can expect to pay $336. The most popular route, (Chicago Midway - San Antonio), can usually be booked for $224.

  • Can I find deals for flights from Midway to San Antonio that include hotel bookings?

    Yes. In addition to deals on Midway to San Antonio flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to San Antonio?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to San Antonio.

  • Can I find deals for business class flights from Midway to San Antonio?

    Yes. Cheapflights offers flight deals from Midway to San Antonio by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to San Antonio?

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to San Antonio (average of $295). Flying from Chicago Midway Airport to San Antonio in March is currently the most expensive (average of $376). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near San Antonio?

Book flights to San Antonio if you plan to visit one of these locations
New Braunfels

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to San Antonio

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Dallas/Fort Worth flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Austin flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Love Field flights
O'Hare Intl to Hobby flights
O'Hare Intl to San Antonio flights
Midway to Hobby flights
Midway to Love Field flights
O'Hare Intl to El Paso flights
Midway to Austin flights
Midway to George Bush Intcntl flights
O'Hare Intl to McAllen flights
O'Hare Intl to Brownsville flights
Midway to El Paso flights
O'Hare Intl to Harlingen flights
O'Hare Intl to Corpus Christi flights
O'Hare Intl to Lubbock flights
O'Hare Intl to Laredo flights
O'Hare Intl to Waco flights
O'Hare Intl to Amarillo flights
O'Hare Intl to Midland flights
O'Hare Intl to Killeen flights
O'Hare Intl to Longview flights
O'Hare Intl to Texarkana flights
O'Hare Intl to Tyler flights
O'Hare Intl to Abilene flights
O'Hare Intl to San Angelo flights
O'Hare Intl to Carlsbad flights

Top 2 airlines flying from Midway to San Antonio

Discover the top 2 airlines that operate flights from Midway to San Antonio. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$158Average$260FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$232Average$413FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.