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Cheap flights from Chicago Midway Airport to San Antonio from $89

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San Antonio departing on 4/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to San Antonio

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
4:33 pm - 12:27 pm
MDW
-
SAT
19h 54m
1 stop
Multiple Airlines Logo
1:22 pm - 8:07 pm
SAT
-
MDW
30h 45m
2 stops
$278Multiple Airlines
Tue, Mar 31 - Mon, Apr 6
Southwest Logo
6:15 pm - 9:05 pm
MDW
-
SAT
2h 50mnonstop
Southwest Logo
11:50 am - 2:25 pm
SAT
-
MDW
2h 35mnonstop
$281Southwest
Sat, Apr 11 - Sat, Apr 18
Frontier Logo
8:00 am - 1:23 pm
MDW
-
SAT
29h 23m
1 stop
Frontier Logo
2:13 pm - 6:13 pm
SAT
-
MDW
28h 00m
1 stop
$282Frontier
Sun, Mar 8 - Tue, Mar 10
Frontier Logo
7:25 am - 1:23 pm
MDW
-
SAT
29h 58m
1 stop
Frontier Logo
2:08 pm - 1:08 pm
SAT
-
MDW
23h 00m
1 stop
$283Frontier
Mon, Mar 16 - Thu, Mar 19
Multiple Airlines Logo
8:39 am - 1:17 pm
MDW
-
SAT
28h 38m
1 stop
Multiple Airlines Logo
9:55 am - 10:19 pm
SAT
-
MDW
12h 24m
2 stops
$284Multiple Airlines
Sun, May 3 - Thu, May 7
Frontier Logo
6:05 am - 2:41 pm
MDW
-
SAT
8h 36m
1 stop
Frontier Logo
2:13 pm - 6:13 pm
SAT
-
MDW
28h 00m
1 stop
$285Frontier
Mon, Mar 9 - Tue, Mar 24
Southwest Logo
9:40 am - 3:50 pm
MDW
-
SAT
6h 10m
2 stops
Southwest Logo
9:00 am - 11:40 am
SAT
-
MDW
2h 40mnonstop
$286Southwest
Wed, Apr 8 - Thu, Apr 16
Southwest Logo
8:35 pm - 11:30 pm
MDW
-
SAT
2h 55mnonstop
Southwest Logo
10:55 am - 4:25 pm
SAT
-
MDW
5h 30m
1 stop
$287Southwest
Wed, Mar 25 - Tue, Mar 31
Southwest Logo
9:40 pm - 12:30 am
MDW
-
SAT
2h 50mnonstop
Southwest Logo
7:15 am - 9:50 am
SAT
-
MDW
2h 35mnonstop
$288Southwest
Fri, Apr 10 - Sat, Apr 18
Southwest Logo
7:25 am - 11:45 am
MDW
-
SAT
4h 20m
1 stop
Southwest Logo
11:50 am - 2:25 pm
SAT
-
MDW
2h 35mnonstop
$290Southwest
Sat, Apr 11 - Sat, Apr 18

Southwest flights from Chicago Midway Airport to San Antonio

Our best Southwest deals on Chicago Midway Airport to San Antonio flight tickets
Southwest
Apr 11
MDW6:15 pmChicago Midway
2h 50m
SAT9:05 pmSan Antonio
Apr 18
SAT11:50 amSan Antonio
2h 35m
MDW2:25 pmChicago Midway
$281
Southwest
Apr 8
MDW9:40 amChicago Midway
6h 10m
2 stops
SAT3:50 pmSan Antonio
Apr 16
SAT9:00 amSan Antonio
2h 40m
MDW11:40 amChicago Midway
$286
Southwest
Mar 25
MDW8:35 pmChicago Midway
2h 55m
SAT11:30 pmSan Antonio
Mar 31
SAT10:55 amSan Antonio
5h 30m
1 stop
MDW4:25 pmChicago Midway
$287

Delta flights from Chicago Midway Airport to San Antonio

Our best Delta deals on Chicago Midway Airport to San Antonio flight tickets
Delta
Apr 18
MDW5:21 pmChicago Midway
7h 25m
1 stop
SAT12:46 amSan Antonio
Apr 25
SAT5:10 amSan Antonio
7h 33m
1 stop
MDW12:43 pmChicago Midway
$297
Delta
Apr 2
MDW6:07 pmChicago Midway
6h 31m
1 stop
SAT12:38 amSan Antonio
Apr 7
SAT5:10 amSan Antonio
7h 19m
1 stop
MDW12:29 pmChicago Midway
$306
Delta
Apr 16
MDW9:29 amChicago Midway
7h 48m
1 stop
SAT5:17 pmSan Antonio
Apr 21
SAT10:42 amSan Antonio
5h 44m
1 stop
MDW4:26 pmChicago Midway
$308

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to San Antonio that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 27, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to San Antonio that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Tue 3/31

4:33 pm-12:27 pm

1 stop19h 54m

San Antonio

Mon 4/6

1:22 pm-8:07 pm

2 stops30h 45m

$278

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sat 4/11

6:15 pm-9:05 pm

Nonstop2h 50m

San Antonio

Sat 4/18

11:50 am-2:25 pm

Nonstop2h 35m

$281

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sun 3/8

8:00 am-1:23 pm

1 stop29h 23m

San Antonio

Tue 3/10

2:13 pm-6:13 pm

1 stop28h 00m

$282

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Mon 3/16

7:25 am-1:23 pm

1 stop29h 58m

San Antonio

Thu 3/19

2:08 pm-1:08 pm

1 stop23h 00m

$283

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sun 5/3

8:39 am-1:17 pm

1 stop28h 38m

San Antonio

Thu 5/7

9:55 am-10:19 pm

2 stops12h 24m

$284

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Mon 3/9

6:05 am-2:41 pm

1 stop8h 36m

San Antonio

Tue 3/24

2:13 pm-6:13 pm

1 stop28h 00m

$285

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 4/8

9:40 am-3:50 pm

2 stops6h 10m

San Antonio

Thu 4/16

9:00 am-11:40 am

Nonstop2h 40m

$286

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 3/25

8:35 pm-11:30 pm

Nonstop2h 55m

San Antonio

Tue 3/31

10:55 am-4:25 pm

1 stop5h 30m

$287

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Fri 4/10

9:40 pm-12:30 am

Nonstop2h 50m

San Antonio

Sat 4/18

7:15 am-9:50 am

Nonstop2h 35m

$288

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sat 4/11

7:25 am-11:45 am

1 stop4h 20m

San Antonio

Sat 4/18

11:50 am-2:25 pm

Nonstop2h 35m

$290

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to San Antonio from

How to get the cheapest flight ticket from Chicago Midway Airport to San Antonio

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to San Antonio?

If you aren’t able to travel during the month of October, then book flights to San Antonio from Chicago Midway Airport during August instead. Flights to San Antonio in August, while not as cheap as those in October, still average around $245.

What is the cheapest day to depart on your flight to San Antonio?

The cheapest day to depart on your flight to San Antonio is on a Tuesday when prices can be found for as low as $357. This is often the case because there is less demand to fly during this day of the week. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to San Antonio on Sunday is $448.

What is the cheapest time of day to depart on your flight to San Antonio?

According to our data, the cheapest time of day to fly to San Antonio is at noon. momondo users have found flights departing from Chicago Midway Airport to San Antonio at noon for as low as $387. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to San Antonio are more costly in the afternoon, with an average ticket price of $397. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago Midway to San Antonio flight route?

Fly from Chicago Midway to San Antonio for the best Chicago Midway - San Antonio flight prices

What cabin class options are available on Chicago Midway to San Antonio flights?

There is only 1 cabin class available to choose from on Chicago Midway to San Antonio flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to San Antonio flights?

You could potentially save up to 31% on your flight if you consider stops on a Chicago Midway Airport to San Antonio flight.

When to book flights from Chicago Midway Airport to San Antonio

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San Antonio according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San Antonio (MDW to SAT) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San Antonio

Best Price Found

$166

Fastest flight time

2h 40m

Direct flights

Every day

Airports in San Antonio

1 airport
The best one-way flight to San Antonio from Chicago Midway Airport in the past 72 hours is $166. The best round-trip flight deal from Chicago Midway Airport to San Antonio found on momondo in the last 72 hours is $367.
The fastest flight from Chicago Midway Airport to San Antonio takes 2h 40m
Direct flights go from Chicago Midway Airport to San Antonio every day.
There is 1 airport in San Antonio. From Chicago Midway Airport there are direct flights to San Antonio (SAT).
Search flight deals

  • How far is Chicago Midway to San Antonio by plane?

    The distance between Chicago Midway and San Antonio is about 1043.4 mi. Typically, this will take 2h 40m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to San Antonio Airport?

    Prices for flights from Chicago Midway Airport to San Antonio Airport refresh daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San Antonio Airport?

  • How old do you have to be to fly from Chicago Midway Airport to San Antonio Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San Antonio Airport.

  • What documentation or ID do you need to fly to San Antonio Airport?

    The necessary travel and health documents for your San Antonio Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to San Antonio?

  • What is the most popular airline from Chicago Midway Airport to San Antonio?

Best airlines flying from Chicago Midway Airport to San Antonio

Compare and see reviews for airlines that fly from Chicago Midway Airport to San Antonio with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $138Free CancellationRating
5.7
3,041 reviews
Search Frontier flights
SouthwestPriceFrom $256Free CancellationRating
8.0
4,301 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to San Antonio

    Southwest operates around 5 flights from Chicago Midway Airport to San Antonio every week. The average price of these flights found in the last 72 hours has been $399, but momondo users have found Southwest deals from Chicago Midway Airport to San Antonio from as low as $256 round-trip. Southwest has been scored 8.0/10 in 4,301 reviews.

Traveling to a place near San Antonio?

Book flights to San Antonio if you plan to visit one of these locations
New Braunfels
Kerrville
Boerne
Pleasanton
Schertz

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San Antonio?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to San Antonio for you.

Can I find flights from Chicago to San Antonio with flexible booking policies on momondo?

momondo does allow users to show only those flights to San Antonio from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to San Antonio?

Once you have performed a search for Chicago to San Antonio flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to San Antonio right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to San Antonio now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to San Antonio and let you know when they change.

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