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Midway

$71+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — MDW
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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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 December 18, 2025.

This CheapOair deal was found by Cheapflights users on 12/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:11 pmSAT - MDW
1 stop26h 47mFrontier
Sun 1/410:50 pmMDW - SAT
1 stop25h 27mFrontier
Deal found 12/16$225
This CheapOair deal was found by Cheapflights users on 12/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:45 amSAT - MDW
1 stop13h 10mFrontier
Sun 1/410:50 pmMDW - SAT
1 stop25h 27mFrontier
Deal found 12/16$245
This CheapOair deal was found by Cheapflights users on 12/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:11 pmSAT - MDW
1 stop26h 47mFrontier
Sun 1/410:50 pmMDW - SAT
1 stop12h 31mFrontier
Deal found 12/16$259
This Expedia deal was found by Cheapflights users on 12/16. 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.
Fri 12/267:11 pmSAT - MDW
1 stop25h 53mFrontier
Sun 2/17:30 amMDW - SAT
1 stop13h 39mFrontier
Deal found 12/16$277
This Booking.com deal was found by Cheapflights users on 12/17. 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.
Wed 12/247:11 pmSAT - MDW
1 stop26h 47mFrontier
Wed 12/318:15 amMDW - SAT
1 stop8h 46mFrontier
Deal found 12/17$301
This Mytrip deal was found by Cheapflights users on 12/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/267:11 pmSAT - MDW
1 stop25h 53mFrontier
Fri 1/26:12 amMDW - SAT
1 stop10h 49mFrontier
Deal found 12/16$327
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/3112:45 pmSAT - MDW
2 stops9h 27mMultiple Airlines
Sun 1/410:50 pmMDW - SAT
1 stop12h 31mMultiple Airlines
Deal found 12/16$394
This Expedia deal was found by Cheapflights users on 12/16. 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.
Sun 12/2110:18 amSAT - MDW
1 stop13h 03mFrontier
Tue 12/232:01 pmMDW - SAT
1 stop10h 16mFrontier
Deal found 12/16$397
This Southwest deal was found by Cheapflights users on 12/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:40 amSAT - MDW
Nonstop2h 35mSouthwest
Fri 1/25:25 amMDW - SAT
1 stop4h 45mSouthwest
Deal found 12/14$407
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Fri 12/2612:45 pmSAT - MDW
2 stops9h 27mMultiple Airlines
Sun 2/15:01 pmMDW - SAT
1 stop24h 02mMultiple Airlines
Deal found 12/16$415

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 December 18, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$216
(Kiwi.com)

One-way from

$71
(CheapOair)

Popular in

November

Cheapest in

September

Average price

$467

Good round-trip deal

$425 or less

Good one-way deal

$228 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. 3% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 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 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 December 18, 2025.
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 1/17

11:18 am-4:29 pm

1 stop5h 11m

Chicago Midway

Sun 1/18

11:21 am-5:15 pm

1 stop5h 54m

$281

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 1/17

5:30 am-12:48 pm

1 stop7h 18m

Chicago Midway

Tue 1/20

1:49 pm-9:34 pm

1 stop7h 45m

$281

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Tue 1/13

11:40 am-7:05 pm

1 stop7h 25m

Chicago Midway

Tue 1/27

8:20 am-11:25 am

Nonstop3h 05m

$287

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 1/14

12:25 pm-9:15 pm

1 stop8h 50m

Chicago Midway

Wed 1/21

8:20 am-11:25 am

Nonstop3h 05m

$287

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Mon 2/9

2:40 pm-5:15 pm

Nonstop2h 35m

Chicago Midway

Sat 2/14

8:40 pm-11:40 pm

Nonstop3h 00m

$304

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 1/17

6:00 am-8:35 am

Nonstop2h 35m

Chicago Midway

Tue 1/20

10:10 am-6:20 pm

1 stop8h 10m

$311

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Tue 3/3

2:10 pm-4:45 pm

Nonstop2h 35m

Chicago Midway

Mon 3/9

9:55 pm-12:50 am

Nonstop2h 55m

$312

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 1/15

5:30 am-12:48 pm

1 stop7h 18m

Chicago Midway

Sat 1/17

6:45 am-12:45 pm

1 stop6h 00m

$324

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Tue 1/6

2:10 pm-4:45 pm

Nonstop2h 35m

$139

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Tue 2/10

2:10 pm-4:45 pm

Nonstop2h 35m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 19 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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
PricelinePrice Accuracy1 starTrust 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 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 Expedia the most. Expedia 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 $287). 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 December 18, 2025.

It’s typically best to fly out from San Antonio to Chicago Midway Airport in the evening. Doing so could potentially save you 45% on the flight price compared to flying in the afternoon, which is usually more expensive.

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
Airports
SAT

For longer trips, economy lots with shuttle service offer better value than parking directly at SAT's garage.

Read more about SATBy Ramsey Qubein
MDW

The Orange Line train connects MDW to downtown Chicago in under 30 minutes, offering a convenient and affordable option.

Read more about MDWBy 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 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 December 18, 2025.
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
7.9
Good
4,252 reviews

Entertainment

7.5

Boarding

8.1

Overall

7.9

Food

7.0

Crew

8.6

Comfort

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

Entertainment

7.5

Boarding

8.1

Overall

7.9

Food

7.0

Crew

8.6

Comfort

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
5.8
Fair
3,080 reviews
Southwest
7.9
Good
4,252 reviews

Entertainment

7.5

Boarding

8.1

Overall

7.9

Food

7.0

Crew

8.6

Comfort

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 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 1 outbound flight 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 $281, Delta can have you in Chicago Midway Airport from San Antonio in 5h 11m. 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 airlines to fly from San Antonio to Chicago Midway Airport one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $94. Southwest flights start at $153 while deals on Delta start at $513 one-way.

  • 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 $468, our data indicates the cheapest price to be $138. The most popular route (San Antonio - Chicago Midway), is priced around $216.

  • 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 $287). 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

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$156Average$222FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$256Average$425FlexibilityNo cancel feeOn-time63%

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