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SAT - MDW

$75 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 6/15
Sat 6/22

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 42,211,976 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
6:48 pm - 5:50 amSAT-MDW
11h 02m1 stop
9:10 pm - 6:10 pmMDW-SAT
21h 00m1 stop
$143Frontier
Find Deal
Wed, May 29 - Tue, Jun 4
6:48 pm - 5:50 amSAT-MDW
11h 02m1 stop
5:55 am - 9:33 pmMDW-SAT
15h 38m1 stop
$149Frontier
Find Deal
Wed, May 29 - Wed, Jun 5
6:27 pm - 5:21 amSAT-MDW
10h 54m1 stop
5:55 am - 9:33 pmMDW-SAT
15h 38m1 stop
$151Frontier
Find Deal
Sat, Jun 22 - Wed, Jun 26
6:40 pm - 6:33 amSAT-MDW
11h 53m1 stop
10:00 pm - 5:44 pmMDW-SAT
19h 44m1 stop
$153Frontier
Find Deal
Tue, Aug 20 - Tue, Aug 27
5:15 am - 12:40 pmSAT-MDW
7h 25m1 stop
9:32 am - 2:51 pmMDW-SAT
5h 19m1 stop
$322Delta
Find Deal
Wed, May 29 - Mon, Jun 3
5:15 am - 12:43 pmSAT-MDW
7h 28m1 stop
3:45 pm - 9:25 pmMDW-SAT
5h 40m1 stop
$352Delta
Find Deal
Tue, Jun 11 - Tue, Jun 18
12:30 pm - 9:47 amSAT-MDW
21h 17m2 stops
2:14 pm - 12:25 amMDW-SAT
34h 11m2 stops
Mon, May 27 - Fri, Jun 7
12:30 pm - 9:47 amSAT-MDW
21h 17m3 stops
2:14 pm - 12:25 amMDW-SAT
34h 11m2 stops
Wed, May 29 - Fri, Jun 7
12:30 pm - 9:47 amSAT-MDW
21h 17m2 stops
8:45 pm - 9:00 amMDW-SAT
12h 15m1 stop
$718Volaris
Find Deal
Wed, May 29 - Tue, Jun 4
12:30 pm - 9:47 amSAT-MDW
21h 17m2 stops
8:45 pm - 9:00 amMDW-SAT
12h 15m1 stop
$770Volaris
Find Deal
Mon, May 27 - Tue, Jun 4

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 $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.

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 5 days before departure. For the absolute cheapest price, our data suggests you should book 19 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 ($75) and Delta ($176). The cheapest round-trip tickets were found on Frontier ($143) and Delta ($322).

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

Each day, there are 4 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 28 flights and there are the same amount of flights each day 4.

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 5:00 pm and lands at 7:35 pm.

Good to know

Low season

January

High season

June

Cheapest flight

$75
Best time to beat the crowds but there is an average 40% 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 $75 for a one-way ticket and $143 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 $396 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 $230 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 10673 reviews
8.2Boarding
8.6Crew
7.9Comfort
7.4Food
8.0Entertainment
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.

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

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

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!!!!!

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
$75
6/5Wed
1 stopFrontier
12h 57mSAT-MDW
$76
6/21Fri
1 stopFrontier
8h 19mSAT-MDW
$79
5/25Sat
1 stopFrontier
11h 02mSAT-MDW
$81
6/11Tue
1 stopDelta
7h 28mSAT-MDW
$176
6/6Thu
2 stops
25h 04mSAT-MDW
$199
7/7Sun
1 stopDelta
7h 09mSAT-MDW
$213
7/7Sun
2 stops
25h 37mSAT-MDW
$269
6/10Mon
2 stopsVolaris
21h 17mSAT-MDW
$381
6/7Fri
2 stopsVolaris
21h 17mSAT-MDW
$390

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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.
5/17Fri
multi-stopFrontier
7h 30mSAT-MDW
5/19Sun
multi-stopFrontier
27h 22mMDW-SAT
$319
5/20Mon
multi-stopFrontier
8h 00mSAT-MDW
5/28Tue
multi-stopFrontier
26h 23mMDW-SAT
$320
5/20Mon
multi-stopFrontier
8h 00mSAT-MDW
5/26Sun
multi-stopFrontier
27h 22mMDW-SAT
$357
5/21Tue
multi-stopDelta
7h 25mSAT-MDW
5/27Mon
multi-stopDelta
7h 15mMDW-SAT
$649
5/17Fri
multi-stopFrontier
7h 30mSAT-MDW
5/19Sun
multi-stopFrontier
9h 34mMDW-SAT
$698
5/19Sun
multi-stop
14h 51mSAT-MDW
5/27Mon
multi-stop
33h 09mMDW-SAT
$706
5/19Sun
multi-stopDelta
7h 27mSAT-MDW
5/21Tue
multi-stopDelta
5h 12mMDW-SAT
$721
5/19Sun
multi-stop
14h 51mSAT-MDW
5/27Mon
multi-stop
25h 14mMDW-SAT
$789
5/19Sun
multi-stopVolaris
14h 51mSAT-MDW
5/26Sun
multi-stopVolaris
12h 15mMDW-SAT
$943
5/19Sun
multi-stopVolaris
14h 51mSAT-MDW
5/27Mon
multi-stopVolaris
12h 15mMDW-SAT
$990

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San Antonio - Chicago Midway Airport Flights

Departure:

San Antonio (undefined)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - San Antonio

Cabin classes: