HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$94+ Cheap flights from San Antonio (SAT) to Midway (MDW)

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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — MDW
Mar 20 — Mar 271
Fri 3/20
Fri 3/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from San Antonio to Midway 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 San Antonio to Midway

Cheapest flights from San Antonio to Midway
Explore the most affordable flight options available from San Antonio to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 18, 2026.

This Expedia deal was found by Cheapflights users on 2/16. 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.
Mon 3/25:08 pm
SAT
-
MDW
1 stop5h 21m
Frontier
Mon 3/96:15 am
MDW
-
SAT
1 stop7h 08m
Frontier
Deal found 2/16$189
This Delta deal was found by Cheapflights users on 2/14. 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 3/285:10 am
SAT
-
MDW
1 stop7h 19m
Delta
Sat 4/44:30 pm
MDW
-
SAT
1 stop8h 07m
Delta
Deal found 2/14$197
This CheapOair deal was found by Cheapflights users on 2/17. 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.
Mon 3/162:40 pm
SAT
-
MDW
1 stop27h 33m
Frontier
Wed 3/1811:19 am
MDW
-
SAT
1 stop26h 04m
Frontier
Deal found 2/17$210
This CheapOair deal was found by Cheapflights users on 2/15. 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.
Thu 2/261:57 pm
SAT
-
MDW
1 stop24h 29m
Frontier
Sun 3/16:00 am
MDW
-
SAT
1 stop10h 19m
Frontier
Deal found 2/15$212
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 5/66:00 am
SAT
-
MDW
1 stop26h 04m
Multiple Airlines
Sat 5/99:14 am
MDW
-
SAT
1 stop8h 45m
Multiple Airlines
Deal found 2/17$217
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 5/66:00 am
SAT
-
MDW
1 stop26h 04m
Multiple Airlines
Mon 5/114:09 pm
MDW
-
SAT
2 stops22h 10m
Multiple Airlines
Deal found 2/15$223
This Booking.com deal was found by Cheapflights users on 2/17. 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 3/152:08 pm
SAT
-
MDW
1 stop24h 13m
Frontier
Wed 3/1811:19 am
MDW
-
SAT
1 stop26h 04m
Frontier
Deal found 2/17$228
This Kiwi.com deal was found by Cheapflights users on 2/17. 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.
Sat 4/186:54 pm
SAT
-
MDW
1 stop13h 10m
Multiple Airlines
Wed 4/227:30 am
MDW
-
SAT
2 stops14h 48m
Multiple Airlines
Deal found 2/17$233
This Delta deal was found by Cheapflights users on 2/14. 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 4/216:20 am
SAT
-
MDW
1 stop5h 47m
Delta
Sat 4/252:12 pm
MDW
-
SAT
1 stop7h 18m
Delta
Deal found 2/14$247
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 4/1710:23 am
SAT
-
MDW
1 stop29h 50m
Multiple Airlines
Mon 4/209:14 am
MDW
-
SAT
1 stop13h 04m
Multiple Airlines
Deal found 2/14$248
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Mon 3/232:40 pm
SAT
-
MDW
1 stop24h 53m
Frontier
Wed 3/2511:25 am
MDW
-
SAT
2 stops12h 52m
Frontier
Deal found 2/16$249

Find flight deals from San Antonio to Midway

Discover tips and strategies to find the most affordable flight options for your journey from San Antonio (SAT) to Midway (MDW). 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 February 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$189
(Expedia)

One-way from

$94
(Super.com)

Popular in

February

Cheapest in

January

Average price

$534

Good round-trip deal

$368 or less

Good one-way deal

$208 or less
Provider with most accurate pricing for San Antonio-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Antonio-Chicago Midway flights.
Search Deals
From San Antonio to Chicago Midway
Search Deals
One-way flight from San Antonio to Chicago Midway
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from San Antonio to Chicago Midway.
Search Deals
Price to beat on a one-way flight from San Antonio to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Antonio to Midway 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 February 18, 2026.
Use the filters below to find and compare flights from San Antonio to Chicago Midway Airport that are best for you.

Fly from

San Antonio

Fly to

Midway

Route

Depart

Return

Price

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 3/28

5:10 am-12:29 pm

1 stop7h 19m

Chicago Midway

Sat 4/4

4:30 pm-12:37 am

1 stop8h 07m

$197

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 3/18

2:45 pm-5:15 pm

Nonstop2h 30m

Chicago Midway

Wed 3/25

8:35 pm-11:30 pm

Nonstop2h 55m

$277

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 4/15

9:05 am-11:40 am

Nonstop2h 35m

Chicago Midway

Sat 4/18

6:15 pm-9:05 pm

Nonstop2h 50m

$277

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 5/6

2:35 pm-5:10 pm

Nonstop2h 35m

Chicago Midway

Sat 5/9

3:00 pm-9:30 pm

1 stop6h 30m

$278

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Tue 5/5

2:35 pm-5:10 pm

Nonstop2h 35m

Chicago Midway

Sat 5/9

6:15 pm-9:05 pm

Nonstop2h 50m

$280

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 4/1

2:15 pm-7:40 pm

1 stop5h 25m

Chicago Midway

Wed 4/8

9:00 pm-11:50 pm

Nonstop2h 50m

$287

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 3/28

5:10 am-12:29 pm

1 stop7h 19m

$99

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 6/13

2:51 pm-9:45 pm

1 stop6h 54m

$99

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 3/14

5:10 am-12:29 pm

1 stop7h 19m

$99

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 4/25

6:39 am-1:32 pm

1 stop6h 53m

$99

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/14

Showing 1-10 of 17 results
1
2

Compare providers for flights from San Antonio to Midway

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 San Antonio to Midway in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star

*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 San Antonio-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Antonio-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Antonio-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Antonio-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub 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 San Antonio-Chicago Midway Airport 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 San Antonio to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from San Antonio 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 San Antonio to Chicago Midway Airport

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

Currently, September is the cheapest month in which you can book a flight from San Antonio to Chicago Midway Airport (average of $138). Flying from San Antonio to Chicago Midway Airport in December is currently the most expensive (average of $277). 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 SAT to MDW?

Find hourly flight availability from San Antonio to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 18, 2026.

When flying from San Antonio to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated February 18, 2026.
Read reviews from past customers who have flown Southwest and Frontier from San Antonio to Chicago Midway Airport. 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
4,294 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

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
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

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
5.7
Fair
3,048 reviews
Southwest
8.0
Very good
4,294 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

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 San Antonio to Midway. 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 from for flights from San Antonio to Chicago Midway?

    Most people fly from San Antonio (SAT) if they book a flight from San Antonio to Chicago Midway. On average, San Antonio has 0 outbound flights to Chicago Midway per day from 2 airlines. San Antonio is conveniently located just 7.6 mi from San Antonio’s city center.

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

    For as low as $189, Frontier can have you in Chicago Midway Airport from San Antonio in 5h 21m. The distance between San Antonio and Chicago Midway Airport is about 1036 mi. This flight may include one or multiple stops.

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

    Currently priced at $141, Frontier will fly you from San Antonio to Chicago Midway Airport and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Southwest for as low as $256. You may be able to fly from San Antonio to Chicago Midway Airport for 65% less than the average price by searching for these airlines.

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

    Looking for the cheapest flight from San Antonio to Chicago Midway Airport? While on average our users pay $329, our data indicates the cheapest price to be $173. The most popular route (San Antonio - Chicago Midway), is priced around $217.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from San Antonio to Midway 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 San Antonio to Chicago Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from San Antonio to Chicago Midway Airport (average of $138). Flying from San Antonio to Chicago Midway Airport in December is currently the most expensive (average of $277). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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.

Top 2 airlines flying from San Antonio to Midway

Discover the top 2 airlines that operate flights from San Antonio to Midway. 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 February 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$141Average$222FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$256Average$405FlexibilityNo 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.