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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 6/29. 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
0 bags
Sat 6/29
Sat 7/6

Search 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
In the last 7 days travelers have searched 42,686,544 times on KAYAK, and here is why:

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
8:51 pm - 9:49 amMDW-SAT
12h 58m1 stop
9:34 pm - 5:14 amSAT-MDW
7h 40m1 stop
$175Frontier
Find Deal
Thu, Jun 13 - Thu, Jun 20
5:55 am - 9:33 pmMDW-SAT
15h 38m1 stop
10:58 pm - 12:00 pmSAT-MDW
13h 02m1 stop
$182Frontier
Find Deal
Wed, Jun 12 - Sun, Jun 16
6:49 pm - 12:17 amMDW-SAT
5h 28m1 stop
5:15 am - 12:42 pmSAT-MDW
7h 27m1 stop
$337Delta
Find Deal
Tue, Jun 18 - Tue, Jul 9
10:41 am - 5:05 pmMDW-SAT
6h 24m1 stop
11:34 am - 6:36 pmSAT-MDW
7h 02m1 stop
$352Delta
Find Deal
Wed, Jun 19 - Tue, Jun 25
9:30 pm - 12:10 amMDW-SAT
2h 40mnonstop
11:55 am - 10:00 pmSAT-MDW
10h 05m1 stop
$414Southwest
Find Deal
Mon, Jun 17 - Thu, Jun 20
10:45 pm - 10:15 amMDW-SAT
11h 30m1 stop
11:55 am - 10:00 pmSAT-MDW
10h 05m1 stop
$423Southwest
Find Deal
Mon, Jun 17 - Thu, Jun 20
9:08 pm - 5:57 pmMDW-SAT
20h 49m3 stops
6:40 pm - 8:18 pmSAT-MDW
25h 38m2 stops
Fri, Jun 21 - Sun, Jun 30
8:00 am - 8:14 amMDW-SAT
24h 14m2 stops
6:40 pm - 8:18 pmSAT-MDW
25h 38m2 stops
Thu, Jun 20 - Thu, Jun 27
8:45 pm - 9:00 amMDW-SAT
12h 15m1 stop
12:30 pm - 9:47 amSAT-MDW
21h 17m2 stops
$1,077Volaris
Find Deal
Sun, Jul 7 - Sat, Jul 13
8:45 pm - 9:00 amMDW-SAT
12h 15m1 stop
12:30 pm - 9:47 amSAT-MDW
21h 17m2 stops
$1,078Volaris
Find Deal
Mon, Jul 8 - Sat, Jul 13

Flights from Midway to San Antonio - Travel Insights & Trends

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 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 Sundays and avoid leaving on a Saturday, as it's usually the priciest day. When flying back from San Antonio, Sunday 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 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 January, where tickets cost $319 on average. On the other hand, the most expensive months are March and April, where the average cost of tickets is $423 and $396 respectively.

How far in advance should I book a flight from Chicago Midway Airport to San Antonio?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to San Antonio, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to San Antonio, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 76 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to San Antonio?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from Chicago Midway Airport to San Antonio found by KAYAK users in the last 72 hours was for $175 on Frontier, followed by Delta ($337). One-way flight deals have also been found from as low as $100 on Frontier and from $166 on Southwest.

How many flights are there between Chicago Midway Airport and San Antonio per day?

Each day, there are 2 nonstop flights that take off from Chicago Midway Airport and land in San Antonio, with an average flight time of 2h 40m. The most common departure time is 8:00 am and most flights take off in the evening. Each week, there are 14 flights and there are the same amount of flights each day 2.

How long does a flight from Chicago Midway Airport to San Antonio take?

Direct flights take on average 2h 40m to travel the 1,036 miles between Chicago Midway Airport and San Antonio.

What’s the earliest departure time from Chicago Midway Airport to San Antonio?

Early birds can take the earliest flight from Chicago Midway Airport at 8:00 am and will be landing in San Antonio at 10:45 am.

What’s the latest departure time from Chicago Midway Airport to San Antonio?

If you prefer to fly at night, the latest flight from Chicago Midway Airport to San Antonio jets off at 10:10 pm and lands at 12:50 am.

Good to know

Low season

April

High season

July

Cheapest flight

$100
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 24% 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 $175 for a round-trip.

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

    No

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

    We unfortunately don’t have that data for this specific 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, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to San Antonio are Delta and Frontier. With an average price for the route of $442 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $258 and an overall rating of 6.2.

  • 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.

See more FAQs

Prefer to fly non-stop from Chicago Midway Airport to San Antonio?

Find which airlines fly direct from Midway to San Antonio, which days they fly and book direct flights.

Nonstop 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

Nonstop 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
See more direct flights

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
DeltaOverall score based on 10457 reviews
7.9Comfort
8.2Boarding
7.4Food
8.6Crew
8.0Entertainment
Airline reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Book cheap flights from Chicago to San Antonio

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to San Antonio found on KAYAK in the last 72 hours.
6/29Sat
1 stopFrontier
8h 22mMDW-SAT
$100
6/30Sun
1 stopFrontier
27h 17mMDW-SAT
$111
6/19Wed
nonstopSouthwest
2h 35mMDW-SAT
$166
7/8Mon
2 stops
27h 52mMDW-SAT
$168
6/19Wed
2 stopsSouthwest
6h 05mMDW-SAT
$180
6/14Fri
1 stopDelta
5h 28mMDW-SAT
$191
6/14Fri
2 stops
20h 49mMDW-SAT
$192
6/10Mon
1 stopDelta
5h 28mMDW-SAT
$300
6/3Mon
1 stopVolaris
12h 15mMDW-SAT
$378
6/3Mon
1 stopVolaris
12h 15mMDW-SAT
$383

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Last minute flights from Midway to San Antonio

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to San Antonio that are departing in the next 10 days.
6/3Mon
multi-stopDelta
6h 35mMDW-SAT
6/6Thu
multi-stopDelta
7h 25mSAT-MDW
$672
6/3Mon
multi-stop
32h 55mMDW-SAT
6/6Thu
multi-stop
36h 59mSAT-MDW
$712
6/3Mon
multi-stop
32h 55mMDW-SAT
6/6Thu
multi-stop
25h 04mSAT-MDW
$713
6/1Sat
multi-stopDelta
5h 12mMDW-SAT
6/1Sat
multi-stopDelta
5h 01mSAT-MDW
$721
6/1Sat
multi-stop
12h 15mMDW-SAT
6/2Sun
multi-stop
25h 03mSAT-MDW
$742
6/3Mon
multi-stopDelta
9h 47mMDW-SAT
6/6Thu
multi-stopDelta
7h 27mSAT-MDW
$1,120
5/31Fri
multi-stopDelta
11h 06mMDW-SAT
6/4Tue
multi-stopDelta
7h 51mSAT-MDW
$1,239
6/2Sun
multi-stopDelta
11h 06mMDW-SAT
6/4Tue
multi-stopDelta
7h 25mSAT-MDW
$1,358
6/3Mon
multi-stopDelta
9h 47mMDW-SAT
6/6Thu
multi-stopDelta
10h 06mSAT-MDW
$1,806

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Chicago Midway Airport - San Antonio Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

San Antonio (SAT)United States

Return flight deals:

San Antonio - Chicago Midway Airport

Cabin classes: