SAT - MDW

$117 Find Cheap Flights from San Antonio to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Antonio to Midway departing on 11/1. 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 Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Antonio to Chicago, 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 San Antonio to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Expert advice
Booking Insights
Flights Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Antonio to Midway 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 San Antonio to Midway

Fri, Aug 22 - Mon, Aug 25
Frontier Logo
5:27 pm - 11:27 pmSAT-MDW
6h 00m1 stop
Frontier Logo
10:58 am - 4:42 pmMDW-SAT
5h 44m1 stop
$226Frontier
Find Deal
Sat, Sep 27 - Tue, Sep 30
Southwest Logo
1:50 pm - 4:25 pmSAT-MDW
2h 35mnonstop
Southwest Logo
8:25 am - 11:10 amMDW-SAT
2h 45mnonstop
$235Southwest
Find Deal
Thu, Oct 16 - Mon, Oct 20
Frontier Logo
3:28 pm - 10:38 pmSAT-MDW
7h 10m1 stop
Frontier Logo
6:15 am - 4:40 pmMDW-SAT
10h 25m1 stop
$238Frontier
Find Deal
Fri, Aug 22 - Mon, Aug 25
Frontier Logo
5:27 pm - 11:27 pmSAT-MDW
6h 00m1 stop
Frontier Logo
10:58 am - 4:42 pmMDW-SAT
5h 44m1 stop
$239Frontier
Find Deal
Thu, Aug 14 - Fri, Aug 22
Frontier Logo
8:14 pm - 11:41 amSAT-MDW
15h 27m1 stop
Frontier Logo
6:31 pm - 2:35 pmMDW-SAT
20h 04m1 stop
$245Frontier
Find Deal
Sat, Sep 27 - Tue, Sep 30
Delta Logo
3:00 pm - 9:10 pmSAT-MDW
6h 10m1 stop
Delta Logo
6:15 pm - 11:25 pmMDW-SAT
5h 10m1 stop
$255Delta
Find Deal
Wed, Sep 3 - Thu, Sep 4
Southwest Logo
2:40 pm - 5:15 pmSAT-MDW
2h 35mnonstop
Southwest Logo
7:40 am - 10:20 amMDW-SAT
2h 40mnonstop
$256Southwest
Find Deal
Fri, Aug 22 - Tue, Aug 26
Southwest Logo
2:50 pm - 5:25 pmSAT-MDW
2h 35mnonstop
Southwest Logo
5:10 pm - 7:50 pmMDW-SAT
2h 40mnonstop
$260Southwest
Find Deal
Wed, Sep 3 - Thu, Sep 4
Delta Logo
6:40 am - 1:36 pmSAT-MDW
6h 56m1 stop
Delta Logo
10:31 am - 4:45 pmMDW-SAT
6h 14m1 stop
$276Delta
Find Deal
Sat, Sep 13 - Mon, Sep 15
Delta Logo
8:00 am - 3:26 pmSAT-MDW
7h 26m1 stop
Delta Logo
6:30 pm - 11:59 pmMDW-SAT
5h 29m1 stop
$280Delta
Find Deal
Expert advice

Expert advice for your flight from San Antonio to Midway

 
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
SAT

Security lines at SAT are exceptionally short. Even on busy days, waits rarely exceed 15 minutes, making it a convenient choice for travelers.

Read more about SATby Brandon Schultz
MDW

The CTA Orange Line from MDW to downtown Chicago is quick and reliable, taking about 25-30 minutes to reach The Loop.

Read more about MDWby Stefanie Waldek
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
Booking Insights

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

Get data-powered insights and trends into flights from San Antonio to Midway 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 San Antonio to Chicago Midway Airport?

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Antonio to Chicago Midway Airport, 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 San Antonio to Chicago Midway Airport is October, where tickets cost $347 (return) on average. On the other hand, the most expensive months are July and June, where the average cost of round-trip tickets is $477 and $457 respectively.

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

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $277 on average.

Good to know

Low seasonApril
Cheapest flight$117
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 3% increase in price.
Flight from San Antonio to Chicago Midway Airport

When to book flights from San Antonio to Midway

Are your dates flexible? Find out the best times to travel from San Antonio to Midway 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 San Antonio to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from San Antonio to Chicago Midway Airport was $117 for a one-way ticket and $226 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

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

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

    The Airbus A319 is the aircraft model that flies most regularly on the San Antonio to Chicago Midway Airport flight route.

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

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

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

    The two airlines most popular with KAYAK users for flights from San Antonio to Chicago are Southwest and Frontier. With an average price for the route of $426 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 $227 and an overall rating of 5.8.

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

    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 San Antonio to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from San Antonio 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 San Antonio to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to San Antonio with another airline. Booking your flights between San Antonio and MDW 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 San Antonio to Chicago Midway Airport?

    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 Chicago Midway Airport from San Antonio 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 San Antonio to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $199 or less one-way and $260 or less round-trip.

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

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

Direct departures

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

Direct returns

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

Reviews of the top airlines flying from San Antonio to Midway

 
See real verified KAYAK customer reviews for airlines flying from San Antonio to Chicago. 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 San Antonio to Midway? 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 4246 reviews
8.6Crew
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

Plz don't take away free bags and free seating

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

The ticketing agents were rude but then we had a great gate agent very nice we had to ride a buss out to where the plane was parked but it was in some back corner of the airport when we got to the plane the captain who was great btw was cleaning the plane because the same rude ticketing agent told them they we not contracted to vacuum the plane. The ride to las Vegas was fine We had a connecting flight to Dallas. The flight was fine but when we arrived in Dallas everyone who flew on any frontier airlines the picked up bags from baggage claim D15 had to wait over a hour for their bags to start we arrived at 11:30pm ish to the gate we didn't leave the baggage clamed till 12:50 am very not happy and i used to fly frontier 4 times a week for work in Denver i will not be using them again

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

Frontier Airlines was AWFUL. I was an hour early for my flight and the lady refused to check me in. I had to purchase a whole new ticket with a different airline.

My flight was canceled I was promised a reginf still not received.

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.