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$74+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SAT
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
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 January 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Fri 2/66:20 am
MDW
-
SAT
1 stop10h 43m
Multiple Airlines
Mon 2/910:35 am
SAT
-
MDW
2 stops11h 44m
Multiple Airlines
Deal found 1/20$273
This Southwest deal was found by Cheapflights users on 1/20. 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.
Tue 2/108:20 am
MDW
-
SAT
Nonstop3h 05m
Southwest
Wed 2/112:10 pm
SAT
-
MDW
Nonstop2h 35m
Southwest
Deal found 1/20$275
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
Fri 3/62:16 pm
MDW
-
SAT
2 stops34h 01m
Multiple Airlines
Thu 3/121:22 pm
SAT
-
MDW
1 stop23h 46m
Multiple Airlines
Deal found 1/21$279
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 2/1212:25 pm
MDW
-
SAT
2 stops21h 05m
Multiple Airlines
Mon 2/165:04 pm
SAT
-
MDW
1 stop26h 03m
Multiple Airlines
Deal found 1/21$282
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Fri 3/62:41 pm
MDW
-
SAT
2 stops18h 25m
Frontier
Thu 3/124:54 pm
SAT
-
MDW
1 stop29h 51m
Frontier
Deal found 1/20$284
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
Fri 3/65:08 pm
MDW
-
SAT
1 stop20h 15m
Multiple Airlines
Sun 3/151:22 pm
SAT
-
MDW
1 stop23h 46m
Multiple Airlines
Deal found 1/21$287
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Fri 2/136:00 am
MDW
-
SAT
1 stop10h 15m
Frontier
Mon 2/165:04 pm
SAT
-
MDW
1 stop26h 03m
Frontier
Deal found 1/20$292
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Fri 3/66:00 am
MDW
-
SAT
1 stop8h 41m
Frontier
Fri 3/132:40 pm
SAT
-
MDW
1 stop9h 11m
Frontier
Deal found 1/20$293
This Delta deal was found by Cheapflights users on 1/20. 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 2/176:40 pm
MDW
-
SAT
1 stop5h 55m
Delta
Tue 2/246:30 am
SAT
-
MDW
1 stop5h 29m
Delta
Deal found 1/20$295
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
Fri 2/137:45 am
MDW
-
SAT
2 stops25h 45m
Multiple Airlines
Mon 2/165:04 pm
SAT
-
MDW
1 stop26h 03m
Multiple Airlines
Deal found 1/21$297

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 January 21, 2026.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$270
(Kiwi.com)

One-way from

$74
(Trip.com)

Popular in

November

Cheapest in

October

Average price

$289

Good round-trip deal

$311 or less

Good one-way deal

$130 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. 3% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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

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 January 21, 2026.
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 2/10

8:20 am-11:25 am

Nonstop3h 05m

San Antonio

Wed 2/11

2:10 pm-4:45 pm

Nonstop2h 35m

$275

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sat 4/18

6:15 pm-9:05 pm

Nonstop2h 50m

San Antonio

Sat 4/25

5:05 am-1:55 pm

2 stops8h 50m

$315

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sat 4/25

6:15 pm-9:05 pm

Nonstop2h 50m

San Antonio

Mon 4/27

2:40 pm-5:15 pm

Nonstop2h 35m

$316

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Thu 4/23

9:40 pm-12:30 am

Nonstop2h 50m

San Antonio

Wed 4/29

5:40 pm-9:45 pm

1 stop4h 05m

$322

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Thu 3/26

9:55 pm-12:50 am

Nonstop2h 55m

San Antonio

Tue 3/31

5:45 am-11:35 am

1 stop5h 50m

$326

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Mon 2/23

6:40 pm-12:35 am

1 stop5h 55m

San Antonio

Wed 2/25

5:30 am-11:59 am

1 stop6h 29m

$330

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Thu 4/9

9:40 pm-12:30 am

Nonstop2h 50m

San Antonio

Thu 4/16

2:40 pm-5:15 pm

Nonstop2h 35m

$333

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 3/25

11:25 am-12:17 am

2 stops12h 52m

San Antonio

Mon 3/30

2:13 pm-3:33 pm

1 stop25h 20m

$335

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Thu 3/19

9:55 pm-12:50 am

Nonstop2h 55m

San Antonio

Sat 3/28

7:35 pm-12:50 am

1 stop5h 15m

$336

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Fri 4/24

9:40 pm-12:30 am

Nonstop2h 50m

San Antonio

Thu 4/30

7:45 pm-11:55 pm

1 stop4h 10m

$343

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 21 results
1
2
3

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
PricelinePrice Accuracy1 starTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
Justfly.comPrice 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 February is currently the most expensive (average of $244). 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 January 21, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 14% 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
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW and SAT

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 January 21, 2026.
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
4,266 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

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
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

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
5.7
Fair
3,057 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

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 $285, Southwest can have you in San Antonio from Chicago Midway Airport in 3h. There are 1036 mi between Chicago Midway Airport and San Antonio. All flights are typically nonstop.

  • 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 $138. Another option worth looking into is Southwest, starting at $256 round trip. You may be able to fly from Chicago Midway Airport to San Antonio for 61% 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 $130. On average you can expect to pay $406. The most popular route, (Chicago Midway - San Antonio), can usually be booked for $235.

  • 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 February is currently the most expensive (average of $244). 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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$138Average$241FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$256Average$412FlexibilityNo cancel feeOn-time63%

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