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Midway

$102+ 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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — MDW
Aug 12 — Aug 191
Tue 8/12
Tue 8/19
1 adult, Economy
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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 August 7, 2025.

Round-trip from

$204
(Southwest)

One-way from

$102
(Southwest)

Popular in

July

Cheapest in

October

Average price

$380

Good round-trip deal

$260 or less

Good one-way deal

$179 or less
From San Antonio to Chicago Midway
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One-way flight from San Antonio to Chicago Midway
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Highest demand for flights based on searches. 6% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from San Antonio to Chicago Midway.
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Price to beat on a one-way flight from San Antonio to Chicago Midway.
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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 August 7, 2025.

This Southwest deal was found by Cheapflights users on 8/7. 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.
Mon 11/32:30 pmSAT - MDW
Nonstop2h 35mSouthwest
Sat 11/85:20 amMDW - SAT
1 stop5h 45mSouthwest
Deal found 8/7$204
This Southwest deal was found by Cheapflights users on 8/7. 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 10/164:55 pmSAT - MDW
1 stop6h 35mSouthwest
Sat 10/185:15 amMDW - SAT
1 stop5h 45mSouthwest
Deal found 8/7$205
This Southwest deal was found by Cheapflights users on 8/5. 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 9/45:50 amSAT - MDW
Nonstop2h 35mSouthwest
Wed 9/175:10 pmMDW - SAT
Nonstop2h 40mSouthwest
Deal found 8/5$212
This Delta deal was found by Cheapflights users on 8/6. 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 9/25:10 amSAT - MDW
1 stop7h 18mDelta
Tue 9/96:00 amMDW - SAT
1 stop5h 00mDelta
Deal found 8/6$217
This Southwest deal was found by Cheapflights users on 8/7. 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 9/187:10 pmSAT - MDW
1 stop4h 55mSouthwest
Tue 9/231:00 pmMDW - SAT
1 stop5h 05mSouthwest
Deal found 8/7$219
This Southwest deal was found by Cheapflights users on 8/7. 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.
Sat 8/302:05 pmSAT - MDW
1 stop4h 30mSouthwest
Tue 9/168:25 amMDW - SAT
Nonstop2h 45mSouthwest
Deal found 8/7$222
This Southwest deal was found by Cheapflights users on 8/6. 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.
Mon 9/87:45 pmSAT - MDW
1 stop4h 05mSouthwest
Wed 9/108:30 amMDW - SAT
2 stops7h 35mSouthwest
Deal found 8/6$224
This Southwest deal was found by Cheapflights users on 8/7. 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 9/32:40 pmSAT - MDW
Nonstop2h 35mSouthwest
Fri 9/57:40 amMDW - SAT
Nonstop2h 40mSouthwest
Deal found 8/7$225
This Southwest deal was found by Cheapflights users on 8/6. 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 9/187:10 pmSAT - MDW
1 stop4h 55mSouthwest
Sun 9/219:00 amMDW - SAT
1 stop6h 25mSouthwest
Deal found 8/6$229
This Frontier deal was found by Cheapflights users on 8/7. 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.
Fri 9/125:40 pmSAT - MDW
1 stop5h 40mFrontier
Mon 9/156:20 amMDW - SAT
1 stop10h 10mFrontier
Deal found 8/7$231

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 August 7, 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

Mon 8/25

2:50 pm-5:25 pm

Nonstop2h 35m

Chicago Midway

Wed 8/27

6:25 am-2:05 pm

1 stop7h 40m

$204

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 10/16

4:55 pm-11:30 pm

1 stop6h 35m

Chicago Midway

Sat 10/18

5:15 am-11:00 am

1 stop5h 45m

$205

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sun 9/14

8:10 pm-12:25 am

1 stop4h 15m

Chicago Midway

Tue 9/16

11:25 am-5:55 pm

1 stop6h 30m

$206

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 9/4

5:50 am-8:25 am

Nonstop2h 35m

Chicago Midway

Wed 9/17

5:10 pm-7:50 pm

Nonstop2h 40m

$212

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 9/3

11:00 am-5:15 pm

2 stops6h 15m

Chicago Midway

Wed 9/10

7:05 am-2:10 pm

1 stop7h 05m

$214

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Tue 9/2

5:10 am-12:28 pm

1 stop7h 18m

Chicago Midway

Tue 9/9

6:00 am-11:00 am

1 stop5h 00m

$217

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 9/18

7:10 pm-12:05 am

1 stop4h 55m

Chicago Midway

Tue 9/23

8:25 am-11:10 am

Nonstop2h 45m

$219

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 9/17

5:35 am-11:45 am

1 stop6h 10m

Chicago Midway

Wed 9/24

8:30 am-4:05 pm

2 stops7h 35m

$224

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sun 10/12

3:28 pm-10:38 pm

1 stop7h 10m

Chicago Midway

Sun 10/19

8:39 am-3:25 pm

1 stop6h 46m

$228

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 9/18

7:10 pm-12:05 am

1 stop4h 55m

Chicago Midway

Sun 9/21

9:00 am-3:25 pm

1 stop6h 25m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/7

Showing 1-10 of 23 results
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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

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, April is the cheapest month in which you can book a flight from San Antonio to Chicago Midway Airport (average of $160). Flying from San Antonio to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 August 7, 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.

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 August 7, 2025.
Read reviews from past customers who have flown Southwest, Delta, 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
4,247 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

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
8.0
Very good
4,247 reviews
Southwest
8.0
Very good
4,247 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

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.
Delta
8.0
Very good
7,987 reviews
Southwest
8.0
Very good
4,247 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

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
5.9
Fair
3,230 reviews
Southwest
8.0
Very good
4,247 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

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.

  • What is the cheapest airline to fly from San Antonio to Chicago Midway Airport round-trip?

    Currently priced at $204, Southwest will fly you from San Antonio to Chicago Midway Airport and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. You may be able to fly from San Antonio to Chicago Midway Airport for 50% less than the average price by searching for this airline.

  • 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 $292, our data indicates the cheapest price to be $138. The most popular route (San Antonio - Chicago Midway), is priced around $162.

  • 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, April is the cheapest month in which you can book a flight from San Antonio to Chicago Midway Airport (average of $160). Flying from San Antonio to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Benton Harbor
Porter
Valparaiso
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 August 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$147Average$227FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$245Average$426FlexibilityNo cancel feeOn-time63%

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