MDW - SAT

$100 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 4/18. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$295
Overall average: $327
Multiple Airlines
Thu 4/9Tue 4/14
MDW - SAT • 1 stop
Cheapest non-stop
$303
Typical prices: $288-$397
Southwest
Mon 4/13Tue 4/14
MDW - SAT • Non-stop
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 $303 (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 53m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $138 (round-trip)
Shortest trip • 6h 42m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 42% 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

Thu, Apr 9 - Tue, Apr 14
Multiple Airlines Logo
5:01 am - 12:27 pm
MDW
-
SAT
7h 26m
1 stop
Multiple Airlines Logo
10:22 am - 7:31 pm
SAT
-
MDW
9h 09m
2 stops
$295Multiple Airlines
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
9:00 pm - 11:50 pm
MDW
-
SAT
2h 50mnonstop
Southwest Logo
9:05 am - 11:40 am
SAT
-
MDW
2h 35mnonstop
$297Southwest
Mon, Apr 13 - Tue, Apr 14
Southwest Logo
9:40 pm - 12:30 am
MDW
-
SAT
2h 50mnonstop
Southwest Logo
9:05 am - 11:40 am
SAT
-
MDW
2h 35mnonstop
$303Southwest
Mon, Apr 13 - Mon, Apr 20
Frontier Logo
6:00 am - 5:05 pm
MDW
-
SAT
11h 05m
1 stop
Frontier Logo
1:51 pm - 7:31 pm
SAT
-
MDW
29h 40m
2 stops
$305Frontier
Mon, Apr 13 - Tue, Apr 14
Multiple Airlines Logo
6:00 am - 5:05 pm
MDW
-
SAT
11h 05m
1 stop
Multiple Airlines Logo
10:22 am - 10:14 pm
SAT
-
MDW
11h 52m
2 stops
$308Multiple Airlines
Mon, Apr 13 - Tue, Apr 14
Southwest Logo
9:40 pm - 12:30 am
MDW
-
SAT
2h 50mnonstop
Southwest Logo
5:40 pm - 9:45 pm
SAT
-
MDW
4h 05m
1 stop
$309Southwest
Tue, Apr 14 - Tue, Apr 21
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
Wed, Jun 3 - Mon, Jun 8
Southwest Logo
5:30 am - 10:25 am
MDW
-
SAT
4h 55m
1 stop
Southwest Logo
3:20 pm - 5:55 pm
SAT
-
MDW
2h 35mnonstop
$313Southwest
Wed, Apr 8 - Wed, Apr 15
Southwest Logo
9:00 pm - 11:50 pm
MDW
-
SAT
2h 50mnonstop
Southwest Logo
5:40 pm - 9:45 pm
SAT
-
MDW
4h 05m
1 stop
$315Southwest
Mon, Apr 13 - Tue, Apr 14
Southwest Logo
6:55 pm - 11:30 pm
MDW
-
SAT
4h 35m
1 stop
Southwest Logo
5:40 pm - 9:45 pm
SAT
-
MDW
4h 05m
1 stop
$318Southwest
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.

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 Sunday, as it's usually the priciest day. When flying back from San Antonio, Wednesday is the cheapest day to fly and Monday 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 $437 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$100
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 9% 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 $100 for a one-way ticket and $295 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 Boeing 737 MAX 8 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 $408 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 $212 and an overall rating of 5.7.

  • 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 $166 or less one-way and $377 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 4321 reviews
8.0Comfort
8.1Boarding
7.5Entertainment
8.6Crew
7.0Food
Airline reviews

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

6.0 GoodChris, Mar 2026
DAL - SAT
Read more Southwest reviews

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.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

No delays and arrived to destination 30 min early. Staff was super friendly.

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.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

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

Information on your arrival and departure airports