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SAT - MDW

Find cheap flights from San Antonio to Chicago Midway Airport from $50

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Antonio to Midway departing on 5/15. 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
Sun 5/19
Sun 5/26

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Antonio to Chicago, 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 San Antonio to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 44,212,662 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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Cheap flight deals from San Antonio to Midway (SAT-MDW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Antonio to Midway 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
9:54 pm - 11:36 amSAT-MDW
13h 42m1 stop
10:55 pm - 11:22 amMDW-SAT
12h 27m1 stop
$107Frontier
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Wed, May 8 - Tue, May 14
10:59 pm - 4:38 pmSAT-MDW
17h 39m1 stop
10:55 pm - 11:22 amMDW-SAT
12h 27m1 stop
$108Frontier
Find Deal
Fri, May 3 - Tue, May 7
9:54 pm - 5:50 amSAT-MDW
7h 56m1 stop
10:22 pm - 8:23 amMDW-SAT
10h 01m1 stop
$120Frontier
Find Deal
Wed, May 15 - Thu, May 23
9:20 am - 4:38 pmSAT-MDW
7h 18m1 stop
10:55 pm - 11:22 amMDW-SAT
12h 27m1 stop
$124Frontier
Find Deal
Sat, May 4 - Tue, May 7
9:23 am - 1:49 pmSAT-MDW
28h 26m1 stop
10:22 pm - 8:23 amMDW-SAT
10h 01m1 stop
$129Frontier
Find Deal
Mon, May 20 - Thu, May 23
2:10 pm - 10:01 pmSAT-MDW
7h 51m1 stop
5:47 pm - 10:44 pmMDW-SAT
4h 57m1 stop
$342Delta
Find Deal
Tue, May 14 - Tue, May 28
6:08 am - 1:35 pmSAT-MDW
7h 27m1 stop
5:00 pm - 11:31 pmMDW-SAT
6h 31m1 stop
$349Delta
Find Deal
Wed, May 15 - Sat, May 18
7:00 am - 2:54 pmSAT-MDW
7h 54m1 stop
6:00 am - 11:12 amMDW-SAT
5h 12m1 stop
$368Delta
Find Deal
Sat, May 4 - Wed, May 8
5:15 am - 12:40 pmSAT-MDW
7h 25m1 stop
5:00 pm - 11:31 pmMDW-SAT
6h 31m1 stop
$369Delta
Find Deal
Thu, May 9 - Sat, May 11
12:30 pm - 9:47 amSAT-MDW
21h 17m2 stops
8:45 pm - 9:00 amMDW-SAT
12h 15m1 stop
$871Volaris
Find Deal
Sun, May 5 - Tue, May 7

Flights from San Antonio to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from San Antonio to Midway 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 San Antonio to Chicago Midway Airport?

The average price of all flights from San Antonio to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
When flying from San Antonio to Chicago Midway Airport, you should consider leaving on a Sunday and avoid Fridays if you are looking for the best rates. For your return to San Antonio, you’ll find the best rates on Wednesdays and the most expensive ones on Saturdays.

What is the cheapest month to fly from San Antonio to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from San Antonio to Chicago Midway Airport, 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 San Antonio to Chicago Midway Airport is October, where tickets cost $201 on average. On the other hand, the most expensive months are June and August, where the average cost of tickets is $394 and $385 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from San Antonio to Chicago Midway Airport, 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 San Antonio to Chicago Midway Airport, you should book around 1 day before departure. For the absolute cheapest price, our data suggests you should book 32 days before departure.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Frontier ($50) and Delta ($171). The cheapest round-trip tickets were found on Frontier ($107) and Delta ($342).

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

Each day, there are 2 nonstop flights that take off from San Antonio and land in Chicago Midway Airport, with an average flight time of 2h 40m. The most common departure time is 5:00 am and most flights take off at night. Each week, there are 14 flights and there are the same amount of flights each day 2.

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

Early birds can take the earliest flight from San Antonio at 5:05 am and will be landing in Chicago Midway Airport at 7:45 am.

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

If you prefer to fly at night, the latest flight from San Antonio to Chicago Midway Airport jets off at 4:40 pm and lands at 7:15 pm.

Good to know

Low season

January

High season

November

Cheapest flight

$50
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from San Antonio to Chicago Midway Airport

When to book flights from San Antonio to Midway

Are your dates flexible? Find out the best times to travel from San Antonio to Midway 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 San Antonio to Chicago Midway Airport flights

  • What is the cheapest flight from San Antonio to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from San Antonio to Chicago Midway Airport was $50 for a one-way ticket and $107 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

    We unfortunately don’t have that data for this specific route.

  • On which days can I fly direct from San Antonio to Chicago Midway Airport?

    There are nonstop flights from San Antonio to Chicago Midway Airport on a daily basis.

  • Which is the best airline for flights from San Antonio to Chicago, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from San Antonio to Chicago are Delta and Frontier. With an average price for the route of $394 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 $224 and an overall rating of 6.3.

  • How does KAYAK find such low prices on flights from San Antonio to Chicago Midway Airport?

    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 San Antonio to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Antonio to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from San Antonio 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 San Antonio to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to San Antonio with another airline. Booking your flights between San Antonio and MDW 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 San Antonio to Chicago Midway Airport?

    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 Chicago Midway Airport from San Antonio 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 San Antonio to Chicago Midway Airport?

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

Nonstop departures

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

Nonstop returns

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
See more direct flights

Top airlines flying from San Antonio to Midway

 
See real verified KAYAK customer reviews for airlines flying from San Antonio to Chicago. 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 San Antonio to Midway? 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 11094 reviews
8.6crew
7.5food
8.2boarding
7.9comfort
8.0entertainment
Airline reviews

Seat back monitors and outlets were dead and not working.

8.0 ExcellentCarl, Apr 2024JFK - FLL
Read more about Delta reviews

Seat back monitors and outlets were dead and not working.

Everything was great except for the seat. The backrest would not stay in the upright position.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Flight delayed about 2 hrs so it made it a VERY late night

It was a crowded flight. They did the best they could.

Service was good for such a short flight. Small plane but smooth flight.

I didn’t like that I could not select my seat and was assigned a seat when I checked in at LAX

Great experience overall. Check in at Austin was congested as they only have about 6 check in kiosks, one was broken, and there was a lot of Spring Break travelers.

I love the free wifi and headrest screens. I would consider Delta even more because of this but the seats aren't so great. The snacks aren't very good in my opinion. I bought a Bloody Mary and that was great! So just be comfortable with better snacks and the airline world will be yours.

Lisa the flight attendent was absolutely wonderful - I loved her energy and you could tell that this crew was amazing family - thank you for making our flight home to LA so very fun! Love and Sun Chips!

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

I paid for extra leg room. The flimsy plastic seat underneath the floatation seat did not line up with the arm rests. It seemed as if the plastic part was zip tied on but immovable. This caused severe uncomfortable for the duration of the flight.

Plane was clean but they do not allow bag drop until 1 hour before flight. Just encouraging late fees and other issues. The worst I have experienced. Total hostage situation, pay or you miss your flight.

Everything was good, and most importantly on time. They have been extremely tardy in some of my flights

I had to cancel within 1hour of the reservation an they put you through hell to . no live customer service desk. I'm handy caped and they make it almost impossible to cancel. They are steeling my money. You should not have that airline on your site. Contact me and I will give you all info. Of what the are doing to me just notable treatment they are set up like that to take people

Horrible flight, rude crew, someone had so mu h perfume on breathing was difficult.

I was singled out for being a Latina flying solo and the attendants took me out of line to put my luggage in the personal item bin to see if it would fly. Keep In mind I had just flown with the same luggage with no problem not even 5 days ago. The tag was sticking out a bit and the attendant was belligerent about charging me $100. I could not refuse because I didn’t wanna cause a scene. But today I felt targeted and embarrassed. I went online and found out that this happens a lot with this airline and to many minority women.

Smooth process and flight. My favorite kind. Uneventful and on-time!

Book cheap flights from San Antonio to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from San Antonio to Chicago found on KAYAK in the last 72 hours.
5/15Wed
1 stopFrontier
7h 56mSAT-MDW
$50
5/18Sat
1 stopFrontier
11h 02mSAT-MDW
$55
5/18Sat
1 stopFrontier
11h 02mSAT-MDW
$56
5/18Sat
1 stopFrontier
11h 02mSAT-MDW
$60
5/10Fri
1 stopFrontier
14h 17mSAT-MDW
$65
5/14Tue
1 stopDelta
6h 32mSAT-MDW
$171
5/14Tue
1 stopDelta
4h 52mSAT-MDW
$172
5/9Thu
1 stopDelta
7h 25mSAT-MDW
$191
7/11Thu
1 stopDelta
7h 29mSAT-MDW
$208
5/4Sat
3 stops
22h 21mSAT-MDW
$215

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Last minute flights from San Antonio to Midway

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 San Antonio to Chicago that are departing in the next 10 days.
4/20Sat
multi-stopFrontier
7h 18mSAT-MDW
4/20Sat
multi-stopFrontier
11h 57mMDW-SAT
$623
4/21Sun
multi-stopFrontier
23h 40mSAT-MDW
4/23Tue
multi-stopFrontier
22h 05mMDW-SAT
$632
4/24Wed
multi-stopDelta
5h 12mSAT-MDW
5/1Wed
multi-stopDelta
7h 38mMDW-SAT
$690
4/24Wed
multi-stopDelta
5h 44mSAT-MDW
4/25Thu
multi-stopDelta
6h 07mMDW-SAT
$710
4/24Wed
multi-stopVolaris
21h 17mSAT-MDW
5/1Wed
multi-stopVolaris
12h 10mMDW-SAT
$813
4/24Wed
multi-stop
28h 40mSAT-MDW
4/26Fri
multi-stop
12h 15mMDW-SAT
$1,059
4/24Wed
multi-stopDelta
7h 30mSAT-MDW
4/25Thu
multi-stopDelta
9h 21mMDW-SAT
$1,163
4/24Wed
multi-stopDelta
9h 24mSAT-MDW
5/1Wed
multi-stopDelta
8h 27mMDW-SAT
$1,345
4/24Wed
multi-stopDelta
10h 59mSAT-MDW
4/25Thu
multi-stopDelta
9h 21mMDW-SAT
$1,731

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San Antonio - Chicago Midway Airport Flights

Departure:

San Antonio (SAT)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - San Antonio

Cabin classes: