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$67+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAT
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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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 September 11, 2025.

Round-trip from

$212
(Kiwi.com)

One-way from

$67
(Southwest)

Popular in

March

Cheapest in

August

Average price

$327

Good round-trip deal

$295 or less

Good one-way deal

$315 or less
From Chicago Midway to San Antonio
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One-way flight from Chicago Midway to San Antonio
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Highest demand for flights based on searches. 6% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago Midway to San Antonio.
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Price to beat on a one-way flight from Chicago Midway to San Antonio.
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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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/11. 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 10/155:30 amMDW - SAT
1 stop4h 10mSouthwest
Tue 10/213:55 pmSAT - MDW
1 stop6h 30mSouthwest
Deal found 9/11$194
This Frontier deal was found by Cheapflights users on 9/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1412:30 pmMDW - SAT
1 stop7h 00mFrontier
Sun 11/1610:46 pmSAT - MDW
2 stops12h 44mFrontier
Deal found 9/11$196
This Booking.com deal was found by Cheapflights users on 9/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/136:15 amMDW - SAT
1 stop10h 35mFrontier
Thu 10/1612:09 pmSAT - MDW
1 stop12h 27mFrontier
Deal found 9/11$209
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/235:20 pmMDW - SAT
2 stops20h 27mMultiple Airlines
Mon 10/275:45 pmSAT - MDW
1 stop17h 53mMultiple Airlines
Deal found 9/10$212
This Southwest deal was found by Cheapflights users on 9/10. 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 10/15:10 pmMDW - SAT
Nonstop2h 40mSouthwest
Sat 10/46:15 amSAT - MDW
Nonstop2h 35mSouthwest
Deal found 9/10$213
This Southwest deal was found by Cheapflights users on 9/10. 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 10/85:15 amMDW - SAT
1 stop4h 35mSouthwest
Wed 10/155:05 pmSAT - MDW
1 stop6h 30mSouthwest
Deal found 9/10$214
This Booking.com deal was found by Cheapflights users on 9/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/276:15 amMDW - SAT
1 stop10h 35mFrontier
Thu 10/308:43 pmSAT - MDW
1 stop14h 47mFrontier
Deal found 9/11$215
This Delta deal was found by Cheapflights users on 9/11. 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.
Tue 10/219:35 amMDW - SAT
1 stop6h 21mDelta
Tue 10/2811:35 amSAT - MDW
1 stop6h 50mDelta
Deal found 9/11$217
This Frontier deal was found by Cheapflights users on 9/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/612:30 pmMDW - SAT
1 stop7h 00mFrontier
Sat 11/84:20 pmSAT - MDW
2 stops19h 10mFrontier
Deal found 9/10$224
This Booking.com deal was found by Cheapflights users on 9/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/136:15 amMDW - SAT
1 stop10h 35mFrontier
Sun 10/268:26 pmSAT - MDW
1 stop14h 50mFrontier
Deal found 9/10$230

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 September 11, 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

Tue 10/21

9:35 am-3:56 pm

1 stop6h 21m

San Antonio

Fri 10/24

11:35 am-6:25 pm

1 stop6h 50m

$217

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Tue 10/21

9:35 am-3:56 pm

1 stop6h 21m

San Antonio

Tue 10/28

6:25 am-1:08 pm

1 stop6h 43m

$217

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 10/1

10:35 am-5:06 pm

1 stop6h 31m

San Antonio

Sat 10/4

3:00 pm-9:10 pm

1 stop6h 10m

$217

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 10/22

9:35 am-3:56 pm

1 stop6h 21m

San Antonio

Fri 10/24

11:35 am-6:25 pm

1 stop6h 50m

$217

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Tue 10/21

1:48 pm-9:10 pm

1 stop7h 22m

San Antonio

Wed 10/29

6:25 am-1:08 pm

1 stop6h 43m

$217

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 11/5

1:48 pm-9:10 pm

1 stop7h 22m

San Antonio

Mon 11/10

5:15 am-12:34 pm

1 stop7h 19m

$217

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 10/1

5:10 pm-7:50 pm

Nonstop2h 40m

San Antonio

Sat 10/4

11:50 am-4:30 pm

1 stop4h 40m

$222

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 11/5

4:55 pm-7:50 pm

Nonstop2h 55m

San Antonio

Fri 11/7

2:15 pm-6:55 pm

1 stop4h 40m

$242

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 11/5

10:00 am-4:30 pm

2 stops6h 30m

San Antonio

Sat 11/15

4:10 pm-8:35 pm

1 stop4h 25m

$250

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Fri 10/17

8:15 pm-11:05 pm

Nonstop2h 50m

San Antonio

Tue 10/21

5:55 am-8:30 am

Nonstop2h 35m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 18 results
1
2

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 September 11, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 12% 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 September 11, 2025.
Read reviews from past customers who have flown Southwest 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
4,248 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chicago Midway Airport to San Antonio?

    For as low as $217, Delta can have you in San Antonio from Chicago Midway Airport in 6h 21m. There are 1036 mi between Chicago Midway Airport and San Antonio.

  • 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 $158. Another option worth looking into is Southwest, starting at $232 round trip. You may be able to fly from Chicago Midway Airport to San Antonio for 57% less than the average price by searching for these airlines.

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

    The cheapest flight price from Chicago Midway Airport to San Antonio is $69. On average you can expect to pay $377. The most popular route, (Chicago Midway - San Antonio), can usually be booked for $133.

  • 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
Kerrville

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Alternative routes for Midway to San Antonio

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$158Average$258FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$232Average$414FlexibilityNo cancel feeOn-time63%

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