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MDW - SAT

$74 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 8/7. 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
Fri 7/12
Fri 7/19

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 44,148,666 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
6:15 am - 9:05 pmMDW-SAT
14h 50m1 stop
7:09 pm - 5:33 amSAT-MDW
10h 24m1 stop
$135Frontier
Find Deal
Wed, Jul 10 - Wed, Jul 17
6:15 am - 9:00 pmMDW-SAT
14h 45m1 stop
6:20 pm - 5:22 amSAT-MDW
11h 02m1 stop
$143Frontier
Find Deal
Wed, Aug 7 - Sat, Aug 10
8:59 pm - 8:52 pmMDW-SAT
23h 53m1 stop
10:59 pm - 11:52 amSAT-MDW
12h 53m1 stop
$149Frontier
Find Deal
Wed, Aug 7 - Mon, Aug 12
5:01 am - 7:04 pmMDW-SAT
14h 03m1 stop
6:20 pm - 5:22 amSAT-MDW
11h 02m1 stop
$156Frontier
Find Deal
Thu, Aug 1 - Sat, Aug 10
6:00 am - 11:08 amMDW-SAT
5h 08m1 stop
10:43 am - 6:02 pmSAT-MDW
7h 19m1 stop
$196Delta
Find Deal
Wed, Sep 4 - Tue, Sep 10
9:18 am - 5:21 pmMDW-SAT
8h 03m1 stop
5:15 am - 12:42 pmSAT-MDW
7h 27m1 stop
$217Delta
Find Deal
Thu, Aug 15 - Sun, Aug 18
12:08 pm - 11:16 pmMDW-SAT
11h 08m3 stops
7:30 pm - 7:40 pmSAT-MDW
24h 10m3 stops
Mon, Jul 15 - Thu, Jul 25
12:08 pm - 11:16 pmMDW-SAT
11h 08m3 stops
8:47 pm - 4:17 pmSAT-MDW
19h 30m3 stops
Mon, Jul 15 - Wed, Jul 24
8:45 pm - 9:00 amMDW-SAT
12h 15m1 stop
12:30 pm - 9:47 amSAT-MDW
21h 17m2 stops
$859Volaris
Find Deal
Tue, Jul 16 - Mon, Jul 22
8:45 pm - 9:00 amMDW-SAT
12h 15m1 stop
12:30 pm - 9:47 amSAT-MDW
21h 17m2 stops
$867Volaris
Find Deal
Sun, Jul 14 - Mon, Jul 22

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 Wednesdays 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 Thursday 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 $135 on Frontier, followed by Delta ($196). One-way flight deals have also been found from as low as $74 on Frontier and from $161 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.

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

$74
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 $74 for a one-way ticket and $135 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 $236 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 10000 reviews
8.0Entertainment
8.6Crew
8.2Boarding
7.4Food
7.9Comfort
Airline reviews

It was very cold because the air conditioner was on high power, and my son got sick.

4.0 OkayAnonymous, Jun 2024ORD - SEA
Read more about Delta reviews

It was very cold because the air conditioner was on high power, and my son got sick.

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

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.

I did not enjoy the trip home on Frontier for several reasons: there is too much cost besides the flight, which was more than I would normally pay, then having to pay for luggage, and carry-on, seat (if you want to reserve when booking) then you must pay over $3 for a can of soda, and $4 for a snack. A cup of water is free.

Did not realize seats did not recline. Best to travel in an exit row... No question

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

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

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.
8/7Wed
1 stopFrontier
14h 45mMDW-SAT
$74
7/23Tue
1 stopFrontier
22h 14mMDW-SAT
$75
8/29Thu
1 stopFrontier
16h 03mMDW-SAT
$79
7/15Mon
1 stopFrontier
15h 44mMDW-SAT
$81
7/5Fri
1 stopDelta
7h 47mMDW-SAT
$161
7/8Mon
2 stops
27h 52mMDW-SAT
$180
7/8Mon
3 stops
27h 52mMDW-SAT
$226
9/3Tue
1 stopDelta
6h 50mMDW-SAT
$244
7/8Mon
2 stopsVolaris
20h 38mMDW-SAT
$459
6/17Mon
1 stopVolaris
12h 15mMDW-SAT
$527

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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.
6/16Sun
multi-stopFrontier
16h 52mMDW-SAT
6/22Sat
multi-stopFrontier
10h 54mSAT-MDW
$207
6/14Fri
multi-stopFrontier
20h 29mMDW-SAT
6/19Wed
multi-stopFrontier
12h 57mSAT-MDW
$223
6/16Sun
multi-stopFrontier
16h 52mMDW-SAT
6/23Sun
multi-stopFrontier
13h 02mSAT-MDW
$232
6/14Fri
multi-stopFrontier
20h 29mMDW-SAT
6/16Sun
multi-stopFrontier
13h 02mSAT-MDW
$244
6/17Mon
multi-stop
27h 51mMDW-SAT
6/20Thu
multi-stop
25h 38mSAT-MDW
$499
6/17Mon
multi-stop
27h 51mMDW-SAT
6/20Thu
multi-stop
25h 38mSAT-MDW
$546
6/15Sat
multi-stopDelta
7h 45mMDW-SAT
6/18Tue
multi-stopDelta
5h 45mSAT-MDW
$718
6/17Mon
multi-stopDelta
5h 09mMDW-SAT
6/25Tue
multi-stopDelta
7h 28mSAT-MDW
$744
6/17Mon
multi-stopVolaris
12h 15mMDW-SAT
6/18Tue
multi-stopVolaris
21h 22mSAT-MDW
$923
6/15Sat
multi-stopVolaris
12h 15mMDW-SAT
6/16Sun
multi-stopVolaris
21h 17mSAT-MDW
$1,469

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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: