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$70+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAT
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:12 amMDW - SAT
1 stop10h 49mFrontier
Wed 12/247:11 pmSAT - MDW
1 stop26h 47mFrontier
Deal found 12/10$207
This Booking.com deal was found by Cheapflights users on 12/11. 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.
Sun 12/2110:50 pmMDW - SAT
1 stop12h 31mFrontier
Wed 12/247:11 pmSAT - MDW
1 stop26h 47mFrontier
Deal found 12/11$220
This CheapOair deal was found by Cheapflights users on 12/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:12 amMDW - SAT
1 stop10h 49mFrontier
Sun 12/216:45 amSAT - MDW
1 stop15h 05mFrontier
Deal found 12/9$233
This Expedia deal was found by Cheapflights users on 12/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:12 amMDW - SAT
1 stop10h 49mFrontier
Tue 12/306:45 amSAT - MDW
1 stop13h 10mFrontier
Deal found 12/11$253
This Southwest deal was found by Cheapflights users on 12/10. 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.
Thu 12/258:10 amMDW - SAT
Nonstop3h 00mSouthwest
Wed 12/312:30 pmSAT - MDW
Nonstop2h 35mSouthwest
Deal found 12/10$261
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Wed 12/316:12 amMDW - SAT
1 stop10h 49mFrontier
Mon 1/57:11 pmSAT - MDW
2 stops27h 06mFrontier
Deal found 12/10$288
This Southwest deal was found by Cheapflights users on 12/10. 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 12/245:35 pmMDW - SAT
1 stop4h 15mSouthwest
Wed 12/316:40 amSAT - MDW
Nonstop2h 35mSouthwest
Deal found 12/10$307
This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:12 amMDW - SAT
1 stop10h 49mFrontier
Sun 12/286:45 amSAT - MDW
1 stop15h 05mFrontier
Deal found 12/10$317

Find 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 December 12, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$192
(Kiwi.com)

One-way from

$70
(Priceline)

Popular in

November

Cheapest in

October

Average price

$432

Good round-trip deal

$437 or less
Provider with most accurate pricing for Chicago Midway-San Antonio flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-San Antonio flights.
Search Deals
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. 0% potential increase in price ($1 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to San Antonio.
Search Deals

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 December 12, 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 1/13

11:39 am-11:52 pm

2 stops12h 13m

San Antonio

Thu 1/15

9:09 am-9:09 am

1 stop24h 00m

$245

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sun 2/22

7:30 am-1:12 pm

1 stop29h 42m

San Antonio

Sat 2/28

7:56 pm-7:59 pm

2 stops24h 03m

$251

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sat 1/17

7:50 pm-10:50 pm

Nonstop3h 00m

San Antonio

Sun 1/18

2:10 pm-4:45 pm

Nonstop2h 35m

$261

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sat 2/14

8:40 pm-11:40 pm

Nonstop3h 00m

San Antonio

Tue 2/17

2:40 pm-5:15 pm

Nonstop2h 35m

$269

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Tue 1/13

8:20 am-11:25 am

Nonstop3h 05m

San Antonio

Sat 1/17

6:00 am-8:35 am

Nonstop2h 35m

$269

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Thu 12/25

4:55 pm-7:50 pm

Nonstop2h 55m

San Antonio

Wed 12/31

6:10 am-1:40 pm

1 stop7h 30m

$271

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 1/7

8:20 am-11:25 am

Nonstop3h 05m

San Antonio

Tue 1/13

2:10 pm-4:45 pm

Nonstop2h 35m

$277

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 1/7

8:20 am-11:25 am

Nonstop3h 05m

San Antonio

Sat 1/10

6:00 am-8:35 am

Nonstop2h 35m

$277

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 1/14

11:39 am-8:14 am

2 stops20h 35m

$90

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 12/31

4:55 pm-7:50 pm

Nonstop2h 55m

$131

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 18 results
1
2

Compare providers for flights from Midway to San Antonio

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to San Antonio in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-San Antonio flights, users find the pricing of Justfly.com to be most consistent on Cheapflights vs. Justfly.com Users can find the same prices on Chicago Midway Airport-San Antonio flight deals on Cheapflights vs. Justfly.com >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San Antonio flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-San Antonio flights, Cheapflights users trust Justfly.com the most. Justfly.com has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-San Antonio flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, December is the cheapest month in which you can book a flight from Chicago Midway Airport to San Antonio (average of $131). Flying from Chicago Midway Airport to San Antonio in May is currently the most expensive (average of $232). 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 December 12, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 13% on flights from Chicago Midway Airport to San Antonio by exploring options for tickets in the evening.

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

AI-powered summary based on content written by travel experts. AI can make mistakes.
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

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 December 12, 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
7.9
Good
4,252 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

7.9

Entertainment

7.5

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
7.9
Good
4,252 reviews
Southwest
7.9
Good
4,252 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

7.9

Entertainment

7.5

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
3,084 reviews
Southwest
7.9
Good
4,252 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

7.9

Entertainment

7.5

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 $261, Frontier can have you in San Antonio from Chicago Midway Airport in 3h. There are 1036 mi between Chicago Midway Airport and San Antonio. This flight may include one or multiple stops.

  • 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 $169. Another option worth looking into is Southwest, starting at $282 round trip. You may be able to fly from Chicago Midway Airport to San Antonio for 54% 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 $347. On average you can expect to pay $505. The most popular route, (Chicago Midway - San Antonio), can usually be booked for $204.

  • 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, December is the cheapest month in which you can book a flight from Chicago Midway Airport to San Antonio (average of $131). Flying from Chicago Midway Airport to San Antonio in May is currently the most expensive (average of $232). 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$169Average$227FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$282Average$427FlexibilityNo cancel feeOn-time63%

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