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Cheap flights from Chicago Midway Airport to San Antonio from $70

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 1/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
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.
Frontier Logo
6:12 am - 5:01 pm
MDW
-
SAT
10h 49m1 stop
Frontier Logo
6:45 am - 9:50 pm
SAT
-
MDW
15h 05m1 stop
$199Frontier
Fri, Dec 19 - Sun, Dec 21
Multiple Airlines Logo
1:00 pm - 11:52 pm
MDW
-
SAT
10h 52m1 stop
Multiple Airlines Logo
6:13 pm - 8:43 am
SAT
-
MDW
14h 30m1 stop
$212Multiple Airlines
Mon, Jan 26 - Fri, Jan 30
Multiple Airlines Logo
6:10 am - 9:40 am
MDW
-
SAT
27h 30m2 stops
Multiple Airlines Logo
6:30 am - 11:09 pm
SAT
-
MDW
16h 39m1 stop
$215Multiple Airlines
Sat, Jan 10 - Mon, Jan 12
Multiple Airlines Logo
6:20 am - 7:33 pm
MDW
-
SAT
13h 13m2 stops
Multiple Airlines Logo
6:30 am - 7:52 pm
SAT
-
MDW
13h 22m1 stop
$222Multiple Airlines
Mon, Jan 26 - Fri, Jan 30
Multiple Airlines Logo
4:21 pm - 11:52 pm
MDW
-
SAT
7h 31m1 stop
Multiple Airlines Logo
6:30 am - 10:19 pm
SAT
-
MDW
15h 49m2 stops
$226Multiple Airlines
Sun, Jan 11 - Tue, Jan 13
Multiple Airlines Logo
5:10 pm - 9:40 am
MDW
-
SAT
16h 30m2 stops
Multiple Airlines Logo
10:13 am - 2:05 pm
SAT
-
MDW
27h 52m1 stop
$228Multiple Airlines
Wed, Jan 7 - Sun, Jan 11
Multiple Airlines Logo
3:05 pm - 3:00 pm
MDW
-
SAT
23h 55m1 stop
Multiple Airlines Logo
6:30 am - 12:02 am
SAT
-
MDW
17h 32m2 stops
$229Multiple Airlines
Fri, Jan 9 - Tue, Jan 13
Frontier Logo
6:12 am - 5:01 pm
MDW
-
SAT
10h 49m1 stop
Frontier Logo
6:45 am - 9:50 pm
SAT
-
MDW
15h 05m1 stop
$233Frontier
Fri, Dec 19 - Sun, Dec 21
Multiple Airlines Logo
5:10 pm - 9:40 am
MDW
-
SAT
16h 30m2 stops
Multiple Airlines Logo
8:59 am - 5:05 pm
SAT
-
MDW
8h 06m1 stop
$241Multiple Airlines
Wed, Jan 7 - Sun, Jan 18
Multiple Airlines Logo
6:20 am - 9:40 am
MDW
-
SAT
27h 20m2 stops
Multiple Airlines Logo
6:13 pm - 11:45 am
SAT
-
MDW
17h 32m1 stop
$251Multiple Airlines
Thu, Jan 22 - Sun, Jan 25

Frontier flights from Chicago Midway Airport to San Antonio

Our best Frontier deals on Chicago Midway Airport to San Antonio flight tickets
Frontier
Dec 19
MDW6:12 amChicago Midway
10h 49m
1 stop
SAT5:01 pmSan Antonio
Dec 21
SAT6:45 amSan Antonio
15h 05m
1 stop
MDW9:50 pmChicago Midway
$199
Find similar
Frontier
Dec 19
MDW6:12 amChicago Midway
10h 49m
1 stop
SAT5:01 pmSan Antonio
Dec 21
SAT6:45 amSan Antonio
15h 05m
1 stop
MDW9:50 pmChicago Midway
$233
Find similar
Frontier
Dec 24
MDW8:15 amChicago Midway
8h 46m
1 stop
SAT5:01 pmSan Antonio
Dec 30
SAT6:45 amSan Antonio
13h 10m
1 stop
MDW7:55 pmChicago Midway
$253
Find similar

Southwest flights from Chicago Midway Airport to San Antonio

Our best Southwest deals on Chicago Midway Airport to San Antonio flight tickets
Southwest
Jan 1
MDW8:10 amChicago Midway
3h 00m
SAT11:10 amSan Antonio
Jan 6
SAT2:10 pmSan Antonio
2h 35m
MDW4:45 pmChicago Midway
$269
Find similar
Southwest
Jan 6
MDW8:20 amChicago Midway
3h 05m
SAT11:25 amSan Antonio
Jan 13
SAT2:10 pmSan Antonio
2h 35m
MDW4:45 pmChicago Midway
$277
Find similar
Southwest
Jan 1
MDW8:25 amChicago Midway
4h 10m
1 stop
SAT12:35 pmSan Antonio
Jan 6
SAT2:10 pmSan Antonio
2h 35m
MDW4:45 pmChicago Midway
$279
Find similar

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 December 9, 2025.
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

Fri 12/19

6:12 am-5:01 pm

1 stop10h 49m

San Antonio

Sun 12/21

6:45 am-9:50 pm

1 stop15h 05m

$199

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Mon 1/26

1:00 pm-11:52 pm

1 stop10h 52m

San Antonio

Fri 1/30

6:13 pm-8:43 am

1 stop14h 30m

$212

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sat 1/10

6:10 am-9:40 am

2 stops27h 30m

San Antonio

Mon 1/12

6:30 am-11:09 pm

1 stop16h 39m

$215

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Mon 1/26

6:20 am-7:33 pm

2 stops13h 13m

San Antonio

Fri 1/30

6:30 am-7:52 pm

1 stop13h 22m

$222

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sun 1/11

4:21 pm-11:52 pm

1 stop7h 31m

San Antonio

Tue 1/13

6:30 am-10:19 pm

2 stops15h 49m

$226

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 1/7

5:10 pm-9:40 am

2 stops16h 30m

San Antonio

Sun 1/11

10:13 am-2:05 pm

1 stop27h 52m

$228

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Fri 1/9

3:05 pm-3:00 pm

1 stop23h 55m

San Antonio

Tue 1/13

6:30 am-12:02 am

2 stops17h 32m

$229

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Fri 12/19

6:12 am-5:01 pm

1 stop10h 49m

San Antonio

Sun 12/21

6:45 am-9:50 pm

1 stop15h 05m

$233

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 1/7

5:10 pm-9:40 am

2 stops16h 30m

San Antonio

Sun 1/18

8:59 am-5:05 pm

1 stop8h 06m

$241

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Thu 1/22

6:20 am-9:40 am

2 stops27h 20m

San Antonio

Sun 1/25

6:13 pm-11:45 am

1 stop17h 32m

$251

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 $383. 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 $444.

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 $386. 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 evening, with an average ticket price of $410. Departure times in the evening 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 41% 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

$437

Fastest flight time

2h 40m

Direct flights

Every day

Airports in San Antonio

1 airport
The best flight deal from Chicago Midway Airport to San Antonio found on momondo in the last 72 hours is $437
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 near San Antonio: 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 3h 00m 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 $169Free CancellationRating
5.8
3,085 reviews
Search Frontier flights
SouthwestPriceFrom $282Free CancellationRating
7.9
4,252 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to San Antonio

    Southwest operates around 12 flights from Chicago Midway Airport to San Antonio every week. The average price of these flights found in the last 72 hours has been $427, but momondo users have found Southwest deals from Chicago Midway Airport to San Antonio from as low as $282 round-trip. Southwest has been scored 7.9/10 in 4,252 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
Schertz
Pleasanton

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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