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Find cheap flights from Chicago Midway Airport to San Antonio from $55

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 5/23. 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 6/8
Sat 6/15

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 43,895,468 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
10:41 pm - 8:27 amMDW-SAT
9h 46m1 stop
9:34 pm - 5:14 amSAT-MDW
7h 40m1 stop
$150Frontier
Find Deal
Thu, Jun 6 - Thu, Jun 13
10:00 pm - 5:44 pmMDW-SAT
19h 44m1 stop
6:40 pm - 6:33 amSAT-MDW
11h 53m1 stop
$154Frontier
Find Deal
Sat, Sep 21 - Sat, Sep 28
10:22 pm - 8:23 amMDW-SAT
10h 01m1 stop
9:50 pm - 5:50 amSAT-MDW
8h 00m1 stop
$155Frontier
Find Deal
Thu, May 30 - Mon, Jun 3
10:00 pm - 5:44 pmMDW-SAT
19h 44m1 stop
6:40 pm - 6:33 amSAT-MDW
11h 53m1 stop
$157Frontier
Find Deal
Thu, Aug 22 - Sat, Aug 24
10:41 am - 11:32 pmMDW-SAT
12h 51m1 stop
6:35 am - 1:05 pmSAT-MDW
6h 30m1 stop
$350Delta
Find Deal
Tue, Jul 2 - Tue, Jul 9
9:33 am - 2:53 pmMDW-SAT
5h 20m1 stop
10:38 am - 5:59 pmSAT-MDW
7h 21m1 stop
$352Delta
Find Deal
Wed, Jul 10 - Tue, Jul 16
6:15 pm - 11:43 pmMDW-SAT
29h 28m3 stops
5:46 am - 5:40 pmSAT-MDW
11h 54m2 stops
Fri, May 31 - Mon, Jun 3
11:25 am - 8:14 amMDW-SAT
20h 49m2 stops
6:40 pm - 8:18 pmSAT-MDW
25h 38m2 stops
Thu, Jun 6 - Thu, Jun 13
8:45 pm - 9:00 amMDW-SAT
12h 15m1 stop
12:30 pm - 9:47 amSAT-MDW
21h 17m2 stops
$859Volaris
Find Deal
Tue, Jun 25 - Sat, Jun 29
8:45 pm - 9:00 amMDW-SAT
12h 15m1 stop
6:56 pm - 9:52 amSAT-MDW
14h 56m1 stop
$862Volaris
Find Deal
Thu, May 30 - Tue, Jun 4

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, Tuesday 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 $150 on Frontier, followed by Delta ($350). One-way flight deals have also been found from as low as $55 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 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

$55
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 $55 for a one-way ticket and $150 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 10778 reviews
8.0Entertainment
7.4Food
8.2Boarding
7.9Comfort
8.6Crew
Airline reviews

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.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

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.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

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 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

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.
5/23Thu
1 stopFrontier
10h 01mMDW-SAT
$55
6/19Wed
1 stopFrontier
15h 38mMDW-SAT
$71
5/21Tue
1 stopFrontier
26h 23mMDW-SAT
$80
5/16Thu
1 stopFrontier
10h 01mMDW-SAT
$81
6/2Sun
1 stopFrontier
27h 22mMDW-SAT
$94
7/2Tue
1 stopDelta
5h 07mMDW-SAT
$176
6/17Mon
1 stopDelta
5h 28mMDW-SAT
$224
5/25Sat
1 stopDelta
7h 26mMDW-SAT
$246
5/15Wed
1 stopDelta
5h 12mMDW-SAT
$349
5/24Fri
2 stops
15h 47mMDW-SAT
$371

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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.
5/14Tue
multi-stopFrontier
12h 27mMDW-SAT
5/18Sat
multi-stopFrontier
9h 27mSAT-MDW
$153
5/14Tue
multi-stopFrontier
12h 27mMDW-SAT
5/15Wed
multi-stopFrontier
7h 56mSAT-MDW
$156
5/14Tue
multi-stopFrontier
22h 05mMDW-SAT
6/14Fri
multi-stopFrontier
21h 06mSAT-MDW
$194
5/11Sat
multi-stopFrontier
11h 57mMDW-SAT
5/18Sat
multi-stopFrontier
11h 02mSAT-MDW
$233
5/14Tue
multi-stopDelta
7h 46mMDW-SAT
5/16Thu
multi-stopDelta
7h 27mSAT-MDW
$689
5/13Mon
multi-stop
12h 15mMDW-SAT
5/16Thu
multi-stop
21h 48mSAT-MDW
$693
5/11Sat
multi-stop
12h 15mMDW-SAT
5/16Thu
multi-stop
21h 48mSAT-MDW
$699
5/13Mon
multi-stopDelta
5h 39mMDW-SAT
5/15Wed
multi-stopDelta
6h 32mSAT-MDW
$702
5/13Mon
multi-stopVolaris
12h 15mMDW-SAT
5/15Wed
multi-stopVolaris
21h 17mSAT-MDW
$773
5/11Sat
multi-stopVolaris
12h 15mMDW-SAT
5/18Sat
multi-stopVolaris
21h 17mSAT-MDW
$778

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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: