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MDW - SAT

$81 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 10/2. 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 7/6
Sat 7/13

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 43,995,393 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
5:01 am - 7:04 pmMDW-SAT
14h 03m1 stop
6:40 pm - 6:33 amSAT-MDW
11h 53m1 stop
$169Frontier
Find Deal
Thu, Aug 8 - Tue, Aug 13
10:41 pm - 8:25 amMDW-SAT
9h 44m1 stop
9:42 pm - 4:45 amSAT-MDW
7h 03m1 stop
$172Frontier
Find Deal
Thu, Jul 4 - Thu, Jul 11
7:05 am - 9:44 pmMDW-SAT
14h 39m1 stop
6:40 pm - 6:33 amSAT-MDW
11h 53m1 stop
$178Frontier
Find Deal
Sat, Aug 10 - Tue, Aug 13
6:00 am - 8:19 amMDW-SAT
26h 19m1 stop
6:40 pm - 6:33 amSAT-MDW
11h 53m1 stop
$183Frontier
Find Deal
Sun, Sep 8 - Fri, Sep 20
9:29 am - 5:27 pmMDW-SAT
7h 58m1 stop
5:18 am - 11:55 amSAT-MDW
6h 37m1 stop
$333Delta
Find Deal
Tue, Jun 25 - Tue, Jul 2
9:29 am - 5:27 pmMDW-SAT
7h 58m1 stop
2:18 pm - 9:46 pmSAT-MDW
7h 28m1 stop
$348Delta
Find Deal
Mon, Jun 24 - Wed, Jun 26
9:08 pm - 12:59 amMDW-SAT
27h 51m2 stops
6:40 pm - 8:17 pmSAT-MDW
25h 37m2 stops
Mon, Jul 1 - Sun, Jul 7
9:08 pm - 1:55 amMDW-SAT
28h 47m3 stops
6:40 pm - 8:18 pmSAT-MDW
25h 38m2 stops
Fri, Jun 28 - Sun, Jun 30
10:55 pm - 9:35 amMDW-SAT
10h 40m1 stop
4:40 pm - 7:15 pmSAT-MDW
2h 35mnonstop
$449Southwest
Find Deal
Mon, Jun 17 - Wed, Jun 19
9:30 pm - 12:10 amMDW-SAT
2h 40mnonstop
4:40 pm - 7:15 pmSAT-MDW
2h 35mnonstop
$456Southwest
Find Deal
Mon, Jun 17 - Wed, Jun 19

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 $169 on Frontier, followed by Delta ($333). One-way flight deals have also been found from as low as $81 on Frontier and from $176 on Delta.

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

Each day, there are between 2 and 4 nonstop flights that take off from Chicago Midway Airport and land in San Antonio, with an average flight time of 2h 38m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 20 flights. The most frequent day of departure is Friday, when 20% of all weekly flights depart. The fewest flights depart on a Tuesday.

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

$81
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 $81 for a one-way ticket and $169 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 $429 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 10368 reviews
7.9Comfort
8.6Crew
8.2Boarding
7.4Food
8.0Entertainment
Airline reviews

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

8.0 Excellentmilton, Jun 2024ANC - MSP
Read more about Delta reviews

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

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.

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

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.

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.
10/2Wed
1 stopFrontier
19h 44mMDW-SAT
$81
7/18Thu
1 stopFrontier
9h 20mMDW-SAT
$97
6/22Sat
1 stopFrontier
8h 22mMDW-SAT
$100
9/25Wed
1 stopDelta
5h 39mMDW-SAT
$176
6/20Thu
1 stopSouthwest
10h 10mMDW-SAT
$177
9/26Thu
1 stopDelta
7h 00mMDW-SAT
$193
6/20Thu
nonstopSouthwest
2h 40mMDW-SAT
$202
6/14Fri
2 stops
20h 49mMDW-SAT
$204
6/14Fri
3 stops
20h 49mMDW-SAT
$233
7/15Mon
2 stopsVolaris
20h 38mMDW-SAT
$403

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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.
6/8Sat
multi-stopFrontier
8h 22mMDW-SAT
6/12Wed
multi-stopFrontier
10h 22mSAT-MDW
$232
6/11Tue
multi-stopFrontier
22h 05mMDW-SAT
6/15Sat
multi-stopFrontier
20h 10mSAT-MDW
$242
6/8Sat
multi-stopFrontier
8h 22mMDW-SAT
6/14Fri
multi-stopFrontier
21h 06mSAT-MDW
$248
6/9Sun
multi-stopFrontier
27h 17mMDW-SAT
6/13Thu
multi-stopFrontier
15h 58mSAT-MDW
$258
6/7Fri
multi-stop
30h 20mMDW-SAT
6/9Sun
multi-stop
25h 04mSAT-MDW
$639
6/7Fri
multi-stop
30h 20mMDW-SAT
6/11Tue
multi-stop
14h 56mSAT-MDW
$659
6/8Sat
multi-stopVolaris
12h 15mMDW-SAT
6/11Tue
multi-stopVolaris
14h 56mSAT-MDW
$788
6/9Sun
multi-stopDelta
5h 09mMDW-SAT
6/11Tue
multi-stopDelta
7h 21mSAT-MDW
$798
6/10Mon
multi-stopDelta
5h 28mMDW-SAT
6/13Thu
multi-stopDelta
7h 09mSAT-MDW
$837
6/8Sat
multi-stopVolaris
12h 15mMDW-SAT
6/12Wed
multi-stopVolaris
21h 17mSAT-MDW
$943

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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: