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SAT - MDW

$70 Find cheap flights from San Antonio to Chicago Midway Airport

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 6/6. 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 6/29
Sat 7/6

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 42,686,544 times on KAYAK, and here is why:

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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
8:19 pm - 3:08 pmSAT-MDW
18h 49m2 stops
6:00 am - 8:19 amMDW-SAT
26h 19m1 stop
$268Frontier
Find Deal
Thu, Aug 8 - Tue, Aug 13
9:04 pm - 5:29 amSAT-MDW
8h 25m1 stop
7:05 am - 7:38 pmMDW-SAT
12h 33m1 stop
$269Frontier
Find Deal
Fri, Jun 28 - Sat, Jul 6
11:34 am - 6:36 pmSAT-MDW
7h 02m1 stop
6:00 am - 1:11 pmMDW-SAT
7h 11m1 stop
$307Delta
Find Deal
Tue, Jun 18 - Tue, Jun 25
12:14 pm - 5:59 pmSAT-MDW
5h 45m1 stop
6:49 pm - 12:17 amMDW-SAT
5h 28m1 stop
$322Delta
Find Deal
Wed, Jun 12 - Tue, Jun 18
11:55 am - 10:00 pmSAT-MDW
10h 05m1 stop
9:20 pm - 11:55 pmMDW-SAT
2h 35mnonstop
$355Southwest
Find Deal
Mon, Jun 17 - Wed, Jun 19
7:50 pm - 12:30 amSAT-MDW
4h 40m1 stop
4:15 pm - 10:40 pmMDW-SAT
6h 25m1 stop
$364Southwest
Find Deal
Mon, Jun 17 - Wed, Jun 19
6:40 pm - 8:17 pmSAT-MDW
25h 37m2 stops
9:07 pm - 12:59 amMDW-SAT
27h 52m2 stops
Thu, Jul 4 - Mon, Jul 8
5:21 am - 7:00 pmSAT-MDW
13h 39m2 stops
7:40 pm - 7:09 pmMDW-SAT
23h 29m2 stops
Fri, Jun 28 - Fri, Jul 5
6:56 pm - 9:47 amSAT-MDW
14h 51m1 stop
8:45 pm - 9:00 amMDW-SAT
12h 15m1 stop
$820Volaris
Find Deal
Sun, Jun 2 - Sun, Jun 9
12:30 pm - 9:47 amSAT-MDW
21h 17m2 stops
8:45 pm - 9:00 amMDW-SAT
12h 15m1 stop
$843Volaris
Find Deal
Mon, Jun 10 - Mon, Jun 17

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 Sundays 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 $209 on average. On the other hand, the most expensive months are April and January, where the average cost of tickets is $581 and $492 respectively.

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 ($70) and Delta ($161). The cheapest round-trip tickets were found on Frontier ($268) and Delta ($307).

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 38m. 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.

How long does a flight from San Antonio to Chicago Midway Airport take?

The average nonstop flight takes 2h 40m, covering a distance of 1,036 miles.

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

Early birds can take the earliest flight from San Antonio at 5:10 am and will be landing in Chicago Midway Airport at 7:50 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 5:00 pm and lands at 7:35 pm.

Good to know

Low season

January

High season

June

Cheapest flight

$70
Best time to beat the crowds but there is an average 39% increase in price.
Most popular time to fly and prices are also 2% lower on average.
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 $70 for a one-way ticket and $268 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 $393 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 $238 and an overall rating of 6.2.

  • 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 10457 reviews
7.4Food
8.0Entertainment
8.2Boarding
8.6Crew
7.9Comfort
Airline reviews

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!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

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.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

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

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

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.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

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

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!!

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.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

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.
6/6Thu
1 stopFrontier
7h 40mSAT-MDW
$70
6/8Sat
1 stopFrontier
10h 54mSAT-MDW
$76
6/12Wed
1 stopFrontier
12h 34mSAT-MDW
$80
7/3Wed
1 stopFrontier
10h 11mSAT-MDW
$108
6/18Tue
1 stopDelta
7h 28mSAT-MDW
$161
6/13Thu
3 stops
37h 33mSAT-MDW
$203
7/2Tue
1 stopDelta
6h 37mSAT-MDW
$209
6/13Thu
2 stops
25h 38mSAT-MDW
$210
6/4Tue
1 stopVolaris
14h 56mSAT-MDW
$340
6/4Tue
2 stopsVolaris
21h 22mSAT-MDW
$415

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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.
5/31Fri
multi-stopFrontier
7h 30mSAT-MDW
6/2Sun
multi-stopFrontier
9h 34mMDW-SAT
$240
6/1Sat
multi-stopFrontier
11h 02mSAT-MDW
6/2Sun
multi-stopFrontier
9h 34mMDW-SAT
$248
6/1Sat
multi-stopFrontier
11h 02mSAT-MDW
6/15Sat
multi-stopFrontier
23h 31mMDW-SAT
$259
6/1Sat
multi-stopFrontier
11h 02mSAT-MDW
6/8Sat
multi-stopFrontier
8h 22mMDW-SAT
$309
6/1Sat
multi-stopFrontier
11h 02mSAT-MDW
6/5Wed
multi-stopFrontier
15h 38mMDW-SAT
$378
6/4Tue
multi-stopDelta
5h 03mSAT-MDW
6/10Mon
multi-stopDelta
5h 28mMDW-SAT
$649
6/2Sun
multi-stopDelta
4h 52mSAT-MDW
6/10Mon
multi-stopDelta
5h 28mMDW-SAT
$672
6/2Sun
multi-stop
25h 03mSAT-MDW
6/9Sun
multi-stop
12h 15mMDW-SAT
$731
6/2Sun
multi-stop
25h 03mSAT-MDW
6/9Sun
multi-stop
36h 19mMDW-SAT
$770
6/2Sun
multi-stopVolaris
14h 51mSAT-MDW
6/9Sun
multi-stopVolaris
12h 15mMDW-SAT
$820

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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: