SAT - MDW

$89 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 6/9. 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

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
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Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from San Antonio to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from San Antonio to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
12:19 pm - 10:38 pmSAT-MDW
10h 19m1 stop
Frontier Logo
9:12 pm - 9:36 amMDW-SAT
12h 24m1 stop
$208Frontier
Find Deal
Wed, Jun 4 - Sun, Jun 8
Frontier Logo
5:38 pm - 11:18 pmSAT-MDW
5h 40m1 stop
Frontier Logo
6:30 am - 4:43 pmMDW-SAT
10h 13m1 stop
$218Frontier
Find Deal
Fri, Jun 6 - Mon, Jun 9
Frontier Logo
12:27 pm - 10:14 pmSAT-MDW
9h 47m1 stop
Frontier Logo
9:12 pm - 9:47 amMDW-SAT
12h 35m1 stop
$220Frontier
Find Deal
Fri, May 23 - Thu, May 29
Frontier Logo
10:52 am - 12:24 pmSAT-MDW
25h 32m1 stop
Frontier Logo
9:12 pm - 9:47 amMDW-SAT
12h 35m1 stop
$230Frontier
Find Deal
Sun, May 18 - Sun, May 25
Southwest Logo
5:35 pm - 8:15 pmSAT-MDW
2h 40mnonstop
Southwest Logo
8:30 am - 11:20 amMDW-SAT
2h 50mnonstop
$297Southwest
Find Deal
Tue, Jun 24 - Wed, Jul 2
Southwest Logo
5:35 pm - 8:15 pmSAT-MDW
2h 40mnonstop
Southwest Logo
7:05 am - 12:50 pmMDW-SAT
5h 45m1 stop
$307Southwest
Find Deal
Tue, Jun 24 - Wed, Jul 2
Delta Logo
5:20 am - 11:53 amSAT-MDW
6h 33m1 stop
Delta Logo
9:16 am - 3:05 pmMDW-SAT
5h 49m1 stop
$317Delta
Find Deal
Sun, May 25 - Wed, May 28
Delta Logo
6:25 am - 1:15 pmSAT-MDW
6h 50m1 stop
Delta Logo
9:16 am - 3:05 pmMDW-SAT
5h 49m1 stop
$342Delta
Find Deal
Sat, May 24 - Mon, May 26
 Logo
7:05 am - 7:46 pmSAT-MDW
12h 41m2 stops
 Logo
8:36 pm - 10:51 pmMDW-SAT
26h 15m2 stops
Fri, Jun 6 - Mon, Jun 9
 Logo
2:55 pm - 2:03 pmSAT-MDW
23h 08m2 stops
 Logo
4:27 pm - 8:55 amMDW-SAT
40h 28m3 stops
Sun, Jun 8 - Wed, Jun 11
Useful Info

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 Wednesdays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Wednesday is the cheapest day to fly and Saturday 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 $340 (return) on average. On the other hand, the most expensive months are July and December, where the average cost of round-trip tickets is $477 and $448 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 $382 on average.

Good to know

Low seasonFebruary
High seasonMarch
Cheapest flight$89
Best time to beat the crowds but there is an average 4% 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 $89 for a one-way ticket and $208 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 Boeing 737-800 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 Delta?

    The two airlines most popular with KAYAK users for flights from San Antonio to Chicago are Southwest and Delta. With an average price for the route of $427 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $446 and an overall rating of 8.0.

  • 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 $243 or less one-way and $348 or less round-trip.

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

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
See more direct flights

Top 3 airlines serving 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 4293 reviews
7.6Entertainment
7.1Food
8.0Comfort
8.6Crew
8.2Boarding
Airline reviews

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

8.0 ExcellentJonathan, Apr 2025AUS - MSY
Read more Southwest reviews

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.

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

The last 30 min or so, they put the heat on full. We thought we were being basted.

I like that it was on time and the staff was friendly.

No space for our carryon and needed to check at plane before boarding !

Flight was ok. Boarding wasn’t fun. Flights were delayed by 12 minutes on each leg.

The plane wasn’t full, so we got the best seats

Flight was delayed due to weather. Crew did a nice job of making us comfortable. No complain complaints.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

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

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