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MDW - SAT

$75 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 6/8. 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 6/15
Sat 6/22

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 42,211,976 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
5:55 am - 9:33 pmMDW-SAT
15h 38m1 stop
10:34 pm - 11:08 amSAT-MDW
12h 34m1 stop
$144Frontier
Find Deal
Wed, Jun 5 - Wed, Jun 12
5:55 am - 9:33 pmMDW-SAT
15h 38m1 stop
9:34 pm - 5:14 amSAT-MDW
7h 40m1 stop
$148Frontier
Find Deal
Wed, Jun 5 - Thu, Jun 6
9:10 pm - 6:10 pmMDW-SAT
21h 00m1 stop
10:34 pm - 11:08 amSAT-MDW
12h 34m1 stop
$149Frontier
Find Deal
Tue, Jun 4 - Wed, Jun 12
10:41 pm - 8:27 amMDW-SAT
9h 46m1 stop
9:23 am - 1:09 pmSAT-MDW
27h 46m1 stop
$151Frontier
Find Deal
Thu, Jun 6 - Mon, Jun 10
3:45 pm - 9:34 pmMDW-SAT
5h 49m1 stop
6:08 am - 1:35 pmSAT-MDW
7h 27m1 stop
$337Delta
Find Deal
Fri, May 31 - Tue, Jun 4
8:45 am - 5:08 pmMDW-SAT
8h 23m1 stop
5:20 am - 10:11 amSAT-MDW
4h 51m1 stop
$352Delta
Find Deal
Wed, May 29 - Sat, Jun 1
9:08 pm - 5:57 pmMDW-SAT
20h 49m2 stops
6:40 pm - 8:18 pmSAT-MDW
25h 38m2 stops
Fri, Jun 14 - Sun, Jun 23
9:08 pm - 5:57 pmMDW-SAT
20h 49m3 stops
6:40 pm - 8:18 pmSAT-MDW
25h 38m2 stops
Fri, Jun 14 - Sun, Jun 23
8:45 pm - 9:00 amMDW-SAT
12h 15m1 stop
12:30 pm - 9:47 amSAT-MDW
21h 17m2 stops
$733Volaris
Find Deal
Tue, Jun 4 - Thu, Jun 6
8:50 pm - 9:00 amMDW-SAT
12h 10m1 stop
12:30 pm - 9:47 amSAT-MDW
21h 17m2 stops
$775Volaris
Find Deal
Wed, Jun 5 - Thu, Jun 6

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 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 September, where tickets cost $315 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 $144 on Frontier, followed by Delta ($337). One-way flight deals have also been found from as low as $75 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 4 nonstop flights that take off from Chicago Midway Airport and land in San Antonio, with an average flight time of 2h 42m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 28 flights and there are the same amount of flights each day 4.

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

$75
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 22% 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 $75 for a one-way ticket and $144 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 10673 reviews
8.0Entertainment
7.4Food
8.2Boarding
7.9Comfort
8.6Crew
Airline reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

6.0 GoodGary, May 2024MSP - TPA
Read more about Delta reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

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.
6/8Sat
1 stopFrontier
8h 22mMDW-SAT
$75
5/21Tue
1 stopFrontier
26h 23mMDW-SAT
$79
6/5Wed
1 stopFrontier
15h 38mMDW-SAT
$80
6/13Thu
1 stopFrontier
12h 58mMDW-SAT
$81
5/29Wed
1 stopDelta
4h 57mMDW-SAT
$161
7/2Tue
1 stopDelta
7h 13mMDW-SAT
$176
6/7Fri
2 stops
21h 23mMDW-SAT
$183
5/31Fri
3 stops
30h 06mMDW-SAT
$191
11/2Sat
2 stopsVolaris
16h 19mMDW-SAT
$393
8/19Mon
2 stopsVolaris
20h 38mMDW-SAT
$411

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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.
5/19Sun
multi-stopFrontier
27h 22mMDW-SAT
5/24Fri
multi-stopFrontier
7h 30mSAT-MDW
$244
5/21Tue
multi-stopFrontier
20h 38mMDW-SAT
5/27Mon
multi-stopFrontier
8h 00mSAT-MDW
$257
5/17Fri
multi-stopFrontier
20h 38mMDW-SAT
5/20Mon
multi-stopFrontier
28h 26mSAT-MDW
$288
5/18Sat
multi-stopDelta
5h 12mMDW-SAT
5/22Wed
multi-stopDelta
7h 27mSAT-MDW
$649
5/20Mon
multi-stopDelta
8h 23mMDW-SAT
5/22Wed
multi-stopDelta
7h 27mSAT-MDW
$672
5/18Sat
multi-stopDelta
6h 31mMDW-SAT
5/21Tue
multi-stopDelta
7h 51mSAT-MDW
$698
5/18Sat
multi-stopDelta
5h 12mMDW-SAT
5/19Sun
multi-stopDelta
7h 27mSAT-MDW
$721
5/21Tue
multi-stopVolaris
12h 15mMDW-SAT
5/27Mon
multi-stopVolaris
21h 17mSAT-MDW
$903
5/18Sat
multi-stopVolaris
12h 15mMDW-SAT
5/19Sun
multi-stopVolaris
21h 17mSAT-MDW
$1,098
5/18Sat
multi-stopVolaris
12h 15mMDW-SAT
5/19Sun
multi-stopVolaris
21h 17mSAT-MDW
$1,121

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Chicago Midway Airport - San Antonio Flights

Departure:

Chicago Midway Airport (undefined)United States

Destination:

San Antonio (SAT)United States

Return flight deals:

San Antonio - Chicago Midway Airport

Cabin classes: