MDW - SAT

$106 Find Cheap Flights from Chicago Midway Airport to San Antonio

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to San Antonio departing on 6/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to San Antonio

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Antonio, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Antonio, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Midway to San Antonio (MDW-SAT)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to San Antonio that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to San Antonio

Fri, Jun 27 - Mon, Jun 30
Frontier Logo
6:20 am - 4:43 pmMDW-SAT
10h 23m1 stop
Frontier Logo
8:50 am - 8:17 pmSAT-MDW
11h 27m1 stop
$210Frontier
Find Deal
Tue, Sep 9 - Mon, Sep 15
Southwest Logo
5:10 pm - 7:50 pmMDW-SAT
2h 40mnonstop
Southwest Logo
5:50 am - 8:25 amSAT-MDW
2h 35mnonstop
$257Southwest
Find Deal
Tue, Sep 9 - Mon, Sep 15
Southwest Logo
3:35 pm - 9:35 pmMDW-SAT
6h 00m1 stop
Southwest Logo
5:50 am - 8:25 amSAT-MDW
2h 35mnonstop
$267Southwest
Find Deal
Mon, Jun 30 - Sun, Jul 20
Frontier Logo
6:20 am - 4:43 pmMDW-SAT
10h 23m1 stop
Frontier Logo
8:14 pm - 11:41 amSAT-MDW
15h 27m1 stop
$275Frontier
Find Deal
Tue, Oct 21 - Tue, Oct 28
Delta Logo
6:00 am - 11:21 amMDW-SAT
5h 21m1 stop
Delta Logo
10:45 am - 4:23 pmSAT-MDW
5h 38m1 stop
$277Delta
Find Deal
Wed, Oct 29 - Fri, Oct 31
Delta Logo
6:00 am - 1:18 pmMDW-SAT
7h 18m1 stop
Delta Logo
5:20 am - 12:32 pmSAT-MDW
7h 12m1 stop
$297Delta
Find Deal
Wed, Jul 30 - Wed, Aug 6
Delta Logo
1:46 pm - 9:25 pmMDW-SAT
7h 39m1 stop
Delta Logo
6:30 am - 11:58 amSAT-MDW
5h 28m1 stop
$307Delta
Find Deal
Tue, Sep 9 - Mon, Sep 15
Southwest Logo
8:30 am - 4:05 pmMDW-SAT
7h 35m2 stops
Southwest Logo
5:20 am - 11:05 amSAT-MDW
5h 45m1 stop
$310Southwest
Find Deal
Thu, Sep 4 - Sun, Sep 7
Southwest Logo
7:40 am - 10:20 amMDW-SAT
2h 40mnonstop
Southwest Logo
6:40 am - 9:15 amSAT-MDW
2h 35mnonstop
$314Southwest
Find Deal
Tue, Jul 1 - Sat, Jul 5
Delta Logo
10:26 am - 3:31 pmMDW-SAT
5h 05m1 stop
Delta Logo
5:20 am - 12:29 pmSAT-MDW
7h 09m1 stop
$317Delta
Find Deal
Expert advice

Expert advice for your flight from Midway to San Antonio

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-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.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
MDW

Midway's compact terminal makes navigation easy, with all concourses accessible from a central check-in and security area.

Read more about MDWby Stefanie Waldek
SAT

The #5 VIA bus offers a convenient ride from SAT to downtown San Antonio, taking about 30 minutes and accommodating large luggage.

Read more about SATby Brandon Schultz
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Brandon Schultz

Brandon Schultz

Expert on SAT

Brandon Schultz

Brandon Schultz

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more
Useful Info

KAYAK's insights & trends for Midway to San Antonio flights

Get data-powered insights and trends into flights from Midway to San Antonio to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago Midway Airport to San Antonio?

The average price of all round-trip flights from Chicago Midway Airport to San Antonio clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago Midway Airport to San Antonio, look for departures on Wednesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from San Antonio, Wednesday is the cheapest day to fly and Friday is the most expensive.

What is the cheapest month to fly from Chicago Midway Airport to San Antonio?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to San Antonio, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to San Antonio is August, where tickets cost $221 (return) on average. On the other hand, the most expensive months are October and March, where the average cost of round-trip tickets is $441 and $433 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to San Antonio?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $374, prices are generally cheapest when you fly direct.

Good to know

Low seasonAugust
High seasonJune
Cheapest flight$106
Best time to beat the crowds with an average 41% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Chicago Midway Airport to San Antonio

When to book flights from Midway to San Antonio

Are your dates flexible? Find out the best times to travel from Midway to San Antonio based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to San Antonio flights

  • What is the cheapest flight from Chicago Midway Airport to San Antonio?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to San Antonio was $106 for a one-way ticket and $210 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and San Antonio?

    No

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to San Antonio?

    American Airlines, and Alaska Airlines offer inflight Wi-Fi service on the Chicago Midway Airport to San Antonio flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to San Antonio?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago Midway Airport to San Antonio flight route.

  • On which days can I fly direct from Chicago Midway Airport to San Antonio?

    There are nonstop flights from Chicago Midway Airport to San Antonio on a daily basis.

  • Which is the best airline for flights from Chicago to San Antonio, Southwest or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to San Antonio are Southwest and Frontier. With an average price for the route of $420 and an overall rating of 8.0, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $260 and an overall rating of 5.9.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to San Antonio?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to San Antonio.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to San Antonio?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Antonio from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to San Antonio?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to San Antonio with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and SAT can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to San Antonio?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to San Antonio from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to San Antonio

  • Looking for a cheap flight? 25% of our users found flights on this route for $188 or less one-way and $359 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to San Antonio?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to San Antonio.
Find which airlines fly direct from Chicago Midway Airport to San Antonio Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to San Antonio

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

San Antonio to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airlines flying from Midway to San Antonio

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San Antonio. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to San Antonio? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4278 reviews
8.6Crew
7.6Entertainment
7.1Food
8.2Boarding
8.0Comfort
Airline reviews

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

6.0 GoodVincent, May 2025MDW - MCO
Read more Southwest reviews

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

First, my flight was a usual flight nothing exceptional or unexpected. Over all it was a normal, good flight! Second, your questionaire is wholly lacking in the proper options to which one can answer a question. Often on short flights, there is no food let alone entertainment so why isn't that reflected in your questionaire? A simple "not applicable" would cover that issue appropriately but no, your form arbitrarily enters an answer based on the initial assessment which normally isn't factual. Until you provide an accurate means of assessing flights, I'll no longer be completing of these unimpressive and misleading assessements. Thank you!

Easy to book and to get check in and get on and off.

Excellent experience. WiFi worked on this leg of My trip

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

No way to get boarding pass on my phone. In order to print the bag ticket a boarding pass is needed. Asked the agent to print me one, they said they typically do not due this as its so much work. I showed the email confirmation and I asked how i could do it my self the agent replied he did not know as there was no link. The flight was delayed due to an attendant forgetting to come to work. On the flight no drinks were offered only for purchase meals.

No way to get boarding pass on my phone. In order to print the bag ticket a boarding pass is needed. Asked the agent to print me one, they said they typically do not due this as its so much work. I showed the email confirmation and I asked how i could do it my self the agent replied he did not know as there was no link. On the flight no drinks were offered only for purchase meals.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

Everything you need to know for your flight from Midway to San Antonio

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