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$141+ 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 5/22. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — MDW
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Priceline
3 stars

Round-trip from

$240
(Frontier)

One-way from

$141
(CheapOair)

Popular in

July

Cheapest in

October

Average price

$427

Good round-trip deal

$348 or less

Good one-way deal

$243 or less
Provider with most accurate pricing for San Antonio-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for San Antonio-Chicago Midway flights.
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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. 2% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 30, 2025.

This Frontier deal was found by Cheapflights users on 4/28. 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 5/2610:42 amSAT - MDW
1 stop9h 35mFrontier
Fri 6/66:30 amMDW - SAT
1 stop10h 13mFrontier
Deal found 4/28$240
This Southwest deal was found by Cheapflights users on 4/29. 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 9/246:30 amSAT - MDW
Nonstop2h 40mSouthwest
Wed 10/15:10 pmMDW - SAT
Nonstop2h 40mSouthwest
Deal found 4/29$297
This Delta deal was found by Cheapflights users on 4/28. 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.
Thu 5/294:15 pmSAT - MDW
1 stop5h 12mDelta
Tue 6/39:20 amMDW - SAT
1 stop8h 00mDelta
Deal found 4/28$317
This Mytrip deal was found by Cheapflights users on 4/29. 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.
Thu 7/33:46 pmSAT - MDW
2 stops22h 18mMultiple Airlines
Mon 7/710:31 amMDW - SAT
3 stops42h 33mMultiple Airlines
Deal found 4/29$490

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 April 30, 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 5/26

10:42 am-8:17 pm

1 stop9h 35m

Chicago Midway

Fri 6/6

6:30 am-4:43 pm

1 stop10h 13m

$240

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 5/29

5:20 am-12:28 pm

1 stop7h 08m

Chicago Midway

Thu 5/29

6:31 pm-12:21 am

1 stop5h 50m

$317

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 6/18

6:20 am-9:00 am

Nonstop2h 40m

Chicago Midway

Sat 6/21

7:40 am-10:25 am

Nonstop2h 45m

$327

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 7/3

3:46 pm-2:04 pm

2 stops22h 18m

Chicago Midway

Mon 7/7

10:31 am-5:04 am

3 stops42h 33m

$490

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 5/22

2:18 pm-3:00 pm

1 stop24h 42m

$141

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Tue 9/23

2:40 pm-5:15 pm

Nonstop2h 35m

$149

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Tue 9/23

5:20 am-12:32 pm

1 stop7h 12m

$159

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 5/29

6:45 pm-6:10 pm

2 stops23h 25m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
Trip.comPrice 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 Priceline the most. Priceline 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, 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 April 30, 2025.

It’s typically best to fly out from San Antonio to Chicago Midway Airport in the evening. Doing so could potentially save you 47% on the flight price compared to flying in the afternoon, which is usually more expensive.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 30, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Frontier from San Antonio to Chicago by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

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
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

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
7,936 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

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
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

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 2 outbound flights to Chicago Midway per day from 3 airlines. San Antonio is conveniently located just 7.6 mi from San Antonio’s city center.

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

    Currently priced at $240, 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. Search Cheapflights for deals from Delta and Southwest - these airlines can fly you to your destination from $317 and $327, respectively. You may be able to fly from San Antonio to Chicago Midway Airport for 41% 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 $141. Southwest flights start at $149 while deals on Delta start at $159 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 $395, our data indicates the cheapest price to be $173. The most popular route (San Antonio - Chicago Midway), is priced around $221.

  • 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 San Antonio?

Book flights to San Antonio if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top 3 airlines flying from San Antonio to Midway

Discover the top 3 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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$147Average$267FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$222Average$427FlexibilityNo cancel feeOn-time63%
DeltaCheapest$301Average$446FlexibilityNo cancel feeOn-timeN/A

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