MDW - SAT

$124 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 5/14. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$297
Typical prices: $484-$342
Southwest
mar. 5/26mar. 6/2
MDW - SAT • Non-stop
Cheapest one-way
$124
Frontier
jue. 5/14
MDW - SAT • 2 stops
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Midway's compact terminal simplifies navigation.
The #5 VIA bus provides a convenient ride to downtown.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $297 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 50m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $138 (round-trip)
Shortest trip • 4h 25m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 44% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to San Antonio!
Flight Deals
Booking Insights
Expert advice
Flight 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

mar., may. 26 - mar., jun. 2
Southwest Logo
9:00 pm - 11:50 pm
MDW
-
SAT
2h 50mnonstop
Southwest Logo
2:35 pm - 5:10 pm
SAT
-
MDW
2h 35mnonstop
$297Southwest
sáb., may. 16 - mar., may. 19
Southwest Logo
10:45 am - 1:35 pm
MDW
-
SAT
2h 50mnonstop
Southwest Logo
2:35 pm - 5:10 pm
SAT
-
MDW
2h 35mnonstop
$303Southwest
mié., may. 20 - mar., may. 26
Southwest Logo
4:40 pm - 11:15 pm
MDW
-
SAT
6h 35m
1 stop
Southwest Logo
2:35 pm - 5:10 pm
SAT
-
MDW
2h 35mnonstop
$307Southwest
sáb., may. 16 - mar., may. 19
Southwest Logo
10:45 am - 1:35 pm
MDW
-
SAT
2h 50mnonstop
Southwest Logo
5:40 pm - 9:45 pm
SAT
-
MDW
4h 05m
1 stop
$309Southwest
mar., may. 26 - mar., jun. 2
Southwest Logo
7:25 am - 12:00 pm
MDW
-
SAT
4h 35m
1 stop
Southwest Logo
5:40 pm - 9:45 pm
SAT
-
MDW
4h 05m
1 stop
$312Southwest
lun., may. 18 - mar., may. 19
Southwest Logo
9:40 pm - 12:30 am
MDW
-
SAT
2h 50mnonstop
Southwest Logo
6:30 am - 11:40 am
SAT
-
MDW
5h 10m
1 stop
$313Southwest
sáb., jun. 13 - mar., jun. 16
Southwest Logo
8:30 pm - 11:10 pm
MDW
-
SAT
2h 40mnonstop
Southwest Logo
2:00 pm - 4:40 pm
SAT
-
MDW
2h 40mnonstop
$314Southwest
mar., jun. 2 - mar., jun. 16
Delta Logo
6:23 am - 1:31 pm
MDW
-
SAT
7h 08m
1 stop
Delta Logo
11:30 am - 6:31 pm
SAT
-
MDW
7h 01m
1 stop
$317Delta
sáb., may. 16 - mar., may. 19
Southwest Logo
10:45 am - 1:35 pm
MDW
-
SAT
2h 50mnonstop
Southwest Logo
1:40 pm - 8:10 pm
SAT
-
MDW
6h 30m
2 stops
$318Southwest
sáb., may. 16 - lun., may. 18
Southwest Logo
7:25 am - 11:45 am
MDW
-
SAT
4h 20m
1 stop
Southwest Logo
2:40 pm - 5:15 pm
SAT
-
MDW
2h 35mnonstop
$319Southwest
Booking Insights

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.

How much is a round-trip flight from Chicago Midway Airport to San Antonio?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to San Antonio departing in May.

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 Tuesdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from San Antonio, Wednesday is the cheapest day to fly and Sunday 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 October, where tickets cost $211 (return) on average. On the other hand, the most expensive months are November and March, where the average cost of round-trip tickets is $480 and $448 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 $367, prices are generally cheapest when you fly direct.

Expert advice

Expert advice for your flight from Midway to San Antonio

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

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.

Brandon Schultz

Brandon Schultz

Expert on SAT

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.

Good to know

Low seasonJanuary
Cheapest flight$124
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 5% 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 $124 for a one-way ticket and $297 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, JetBlue, 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 Embraer 175 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 $441 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 $222 and an overall rating of 5.6.

  • 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 $154 or less one-way and $321 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 4314 reviews
8.1Boarding
7.0Food
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

4.0 OkayDavid, Apr 2026
COS - DAL
Read more Southwest reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

The seat was not comfortable. 1D. My back was sore all night and the next day.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

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

Information on your arrival and departure airports