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Midway

$86+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — MDW
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Find 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 October 14, 2025.

This Booking.com deal was found by Cheapflights users on 10/13. 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.
Thu 12/1110:13 amSAT - MDW
1 stop10h 23mFrontier
Mon 12/156:00 amMDW - SAT
1 stop11h 47mFrontier
Deal found 10/13$162
This Frontier deal was found by Cheapflights users on 10/12. 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.
Mon 10/2710:54 amSAT - MDW
1 stop10h 52mFrontier
Thu 11/612:30 pmMDW - SAT
1 stop6h 36mFrontier
Deal found 10/12$172
This Booking.com deal was found by Cheapflights users on 10/13. 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.
Fri 10/247:10 pmSAT - MDW
1 stop15h 11mFrontier
Mon 10/276:15 amMDW - SAT
1 stop10h 35mFrontier
Deal found 10/13$181
This Trip.com deal was found by Cheapflights users on 10/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:33 pmSAT - MDW
1 stop18h 37mFrontier
Mon 12/156:00 amMDW - SAT
1 stop11h 47mFrontier
Deal found 10/13$190
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 10/275:45 pmSAT - MDW
1 stop17h 53mFrontier
Fri 10/316:20 amMDW - SAT
1 stop10h 20mFrontier
Deal found 10/12$198
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/83:12 pmSAT - MDW
1 stop20h 18mFrontier
Sat 11/151:37 pmMDW - SAT
2 stops29h 53mFrontier
Deal found 10/11$199
This Frontier deal was found by Cheapflights users on 10/12. 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.
Sun 11/29:59 amSAT - MDW
1 stop7h 23mFrontier
Mon 11/36:20 amMDW - SAT
1 stop10h 20mFrontier
Deal found 10/12$200
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 11/510:58 amSAT - MDW
1 stop22h 14mMultiple Airlines
Thu 11/61:37 pmMDW - SAT
2 stops29h 53mMultiple Airlines
Deal found 10/12$215
This Frontier deal was found by Cheapflights users on 10/12. 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.
Mon 11/310:04 amSAT - MDW
1 stop6h 48mFrontier
Fri 11/76:15 amMDW - SAT
1 stop10h 25mFrontier
Deal found 10/12$217
This Frontier deal was found by Cheapflights users on 10/12. 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.
Sun 11/99:59 amSAT - MDW
1 stop7h 23mFrontier
Mon 11/106:15 amMDW - SAT
1 stop10h 25mFrontier
Deal found 10/12$218

Cheap 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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$162
(Booking.com)

One-way from

$86
(Priceline)

Popular in

July

Cheapest in

September

Average price

$329

Good round-trip deal

$317 or less

Good one-way deal

$229 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. 9% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 14, 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

Fri 12/5

10:13 am-8:36 pm

1 stop10h 23m

Chicago Midway

Mon 12/8

6:00 am-5:47 pm

1 stop11h 47m

$296

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 11/12

6:40 am-9:15 am

Nonstop2h 35m

Chicago Midway

Wed 11/19

4:55 pm-7:50 pm

Nonstop2h 55m

$297

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 10/31

5:25 am-12:28 pm

1 stop7h 03m

Chicago Midway

Tue 11/4

5:09 pm-12:20 am

1 stop7h 11m

$307

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 11/8

6:50 am-11:45 am

1 stop4h 55m

Chicago Midway

Sat 11/8

1:15 pm-8:50 pm

1 stop7h 35m

$317

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Tue 11/4

11:35 am-6:25 pm

1 stop6h 50m

Chicago Midway

Sat 11/8

4:23 pm-12:20 am

1 stop7h 57m

$317

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 11/8

5:15 pm-10:14 pm

1 stop4h 59m

Chicago Midway

Wed 11/12

5:34 pm-12:38 am

1 stop7h 04m

$317

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 12/10

5:15 pm-11:49 pm

1 stop6h 34m

Chicago Midway

Tue 12/16

9:34 am-4:04 pm

1 stop6h 30m

$317

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 11/5

5:25 am-12:28 pm

1 stop7h 03m

Chicago Midway

Tue 11/11

6:00 am-1:41 pm

1 stop7h 41m

$317

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 11/13

3:45 pm-6:20 pm

Nonstop2h 35m

Chicago Midway

Thu 11/27

5:45 am-12:20 pm

1 stop6h 35m

$322

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 12/31

6:40 am-9:15 am

Nonstop2h 35m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

Showing 1-10 of 20 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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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, December is the cheapest month in which you can book a flight from San Antonio to Chicago Midway Airport (average of $120). Flying from San Antonio to Chicago Midway Airport in May is currently the most expensive (average of $194). 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 October 14, 2025.

It’s typically best to fly out from San Antonio to Chicago Midway Airport in the evening. Doing so could potentially save you 46% 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

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 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 October 14, 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
8.0
Very good
4,235 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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
8.0
Very good
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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
3,136 reviews
Southwest
8.0
Very good
4,235 reviews

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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 2 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 $297, Frontier can have you in Chicago Midway Airport from San Antonio in 2h 35m. 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 $156, 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 61% 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 $350, our data indicates the cheapest price to be $168. The most popular route (San Antonio - Chicago Midway), is priced around $223.

  • 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, December is the cheapest month in which you can book a flight from San Antonio to Chicago Midway Airport (average of $120). Flying from San Antonio to Chicago Midway Airport in May is currently the most expensive (average of $194). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

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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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$156Average$227FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$256Average$425FlexibilityNo cancel feeOn-time63%

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