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Cheap flights from Chicago Midway Airport to San Antonio from $80

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 12/31. 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.
Frontier Logo
12:30 pm - 7:30 pmMDW-SAT
7h 00m1 stop
Frontier Logo
9:59 am - 5:22 pmSAT-MDW
7h 23m1 stop
$156Frontier
Find Deal
Fri, Nov 7 - Sun, Nov 9
Frontier Logo
6:20 am - 4:40 pmMDW-SAT
10h 20m1 stop
Frontier Logo
8:25 pm - 11:30 amSAT-MDW
15h 05m1 stop
$158Frontier
Find Deal
Mon, Nov 3 - Thu, Nov 6
Frontier Logo
12:18 pm - 7:00 pmMDW-SAT
6h 42m1 stop
Frontier Logo
7:56 pm - 11:08 amSAT-MDW
15h 12m1 stop
$163Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
Frontier Logo
12:30 pm - 7:30 pmMDW-SAT
7h 00m1 stop
Frontier Logo
3:12 pm - 11:30 amSAT-MDW
20h 18m1 stop
$164Frontier
Find Deal
Mon, Nov 10 - Sat, Nov 15
Delta Logo
11:05 am - 4:43 pmMDW-SAT
5h 38m1 stop
Delta Logo
6:22 pm - 11:47 pmSAT-MDW
5h 25m1 stop
$199Delta
Find Deal
Sat, Dec 6 - Sun, Dec 7
Delta Logo
10:36 am - 3:47 pmMDW-SAT
5h 11m1 stop
Delta Logo
5:20 am - 12:34 pmSAT-MDW
7h 14m1 stop
$201Delta
Find Deal
Fri, Dec 5 - Mon, Dec 8
Multiple Airlines Logo
1:56 pm - 6:32 pmMDW-SAT
28h 36m2 stops
Multiple Airlines Logo
8:25 pm - 11:30 amSAT-MDW
15h 05m1 stop
$214Multiple Airlines
Find Deal
Tue, Nov 11 - Sun, Nov 16
Multiple Airlines Logo
6:15 am - 8:30 pmMDW-SAT
14h 15m1 stop
Multiple Airlines Logo
1:55 pm - 9:17 amSAT-MDW
19h 22m2 stops
$215Multiple Airlines
Find Deal
Fri, Dec 5 - Mon, Dec 8
Southwest Logo
9:25 am - 12:25 pmMDW-SAT
3h 00mnonstop
Southwest Logo
6:40 am - 9:15 amSAT-MDW
2h 35mnonstop
$222Southwest
Find Deal
Sat, Dec 6 - Mon, Dec 8
Southwest Logo
9:25 am - 12:25 pmMDW-SAT
3h 00mnonstop
Southwest Logo
6:10 am - 8:45 amSAT-MDW
2h 35mnonstop
$236Southwest
Find Deal
Sat, Dec 6 - Sun, Dec 7

Delta flights from Chicago Midway Airport to San Antonio

Our best Delta deals on Chicago Midway Airport to San Antonio flight tickets
Delta
Dec 6
MDW11:05 amChicago Midway
5h 38m
1 stop
SAT4:43 pmSan Antonio
Dec 7
SAT6:22 pmSan Antonio
5h 25m
1 stop
MDW11:47 pmChicago Midway
$199
Find similar
Delta
Dec 5
MDW10:36 amChicago Midway
5h 11m
1 stop
SAT3:47 pmSan Antonio
Dec 8
SAT5:20 amSan Antonio
7h 14m
1 stop
MDW12:34 pmChicago Midway
$201
Find similar
Delta
Dec 16
MDW10:36 amChicago Midway
5h 11m
1 stop
SAT3:47 pmSan Antonio
Jan 1
SAT7:05 amSan Antonio
7h 39m
1 stop
MDW2:44 pmChicago Midway
$238
Find similar

Frontier flights from Chicago Midway Airport to San Antonio

Our best Frontier deals on Chicago Midway Airport to San Antonio flight tickets
Frontier
Oct 30
MDW12:30 pmChicago Midway
7h 18m
1 stop
SAT7:48 pmSan Antonio
Nov 3
SAT10:04 amSan Antonio
6h 48m
1 stop
MDW4:52 pmChicago Midway
$156
Find similar
Frontier
Nov 3
MDW6:20 amChicago Midway
10h 20m
1 stop
SAT4:40 pmSan Antonio
Nov 6
SAT8:25 pmSan Antonio
15h 05m
1 stop
MDW11:30 amChicago Midway
$158
Find similar
Frontier
Oct 30
MDW12:30 pmChicago Midway
7h 18m
1 stop
SAT7:48 pmSan Antonio
Nov 3
SAT10:04 amSan Antonio
6h 48m
1 stop
MDW4:52 pmChicago Midway
$163
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 October 22, 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 11/7

12:30 pm-7:30 pm

1 stop7h 00m

San Antonio

Sun 11/9

9:59 am-5:22 pm

1 stop7h 23m

$156

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Mon 11/3

6:20 am-4:40 pm

1 stop10h 20m

San Antonio

Thu 11/6

8:25 pm-11:30 am

1 stop15h 05m

$158

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Fri 12/5

12:18 pm-7:00 pm

1 stop6h 42m

San Antonio

Sun 12/7

7:56 pm-11:08 am

1 stop15h 12m

$163

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Mon 11/10

12:30 pm-7:30 pm

1 stop7h 00m

San Antonio

Sat 11/15

3:12 pm-11:30 am

1 stop20h 18m

$164

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sat 12/6

11:05 am-4:43 pm

1 stop5h 38m

San Antonio

Sun 12/7

6:22 pm-11:47 pm

1 stop5h 25m

$199

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Fri 12/5

10:36 am-3:47 pm

1 stop5h 11m

San Antonio

Mon 12/8

5:20 am-12:34 pm

1 stop7h 14m

$201

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Tue 11/11

1:56 pm-6:32 pm

2 stops28h 36m

San Antonio

Sun 11/16

8:25 pm-11:30 am

1 stop15h 05m

$214

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Fri 12/5

6:15 am-8:30 pm

1 stop14h 15m

San Antonio

Mon 12/8

1:55 pm-9:17 am

2 stops19h 22m

$215

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sat 12/6

9:25 am-12:25 pm

Nonstop3h 00m

San Antonio

Mon 12/8

6:40 am-9:15 am

Nonstop2h 35m

$222

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sat 12/6

9:25 am-12:25 pm

Nonstop3h 00m

San Antonio

Sun 12/7

6:10 am-8:45 am

Nonstop2h 35m

$236

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 August, then book flights to San Antonio from Chicago Midway Airport during July instead. Flights to San Antonio in July, while not as cheap as those in August, still average around $317.

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 Wednesday when prices can be found for as low as $389. 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 $455.

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 $384. 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 morning, with an average ticket price of $426. Departure times in the morning 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 21% 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

$158

Fastest flight time

2h 45m

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 $158. The best round-trip flight deal from Chicago Midway Airport to San Antonio found on momondo in the last 72 hours is $287.
The fastest flight from Chicago Midway Airport to San Antonio takes 2h 45m
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 2h 55m 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 $158Free CancellationRating
5.8
3,130 reviews
Search Frontier flights
SouthwestPriceFrom $282Free CancellationRating
8.0
4,237 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to San Antonio

    Southwest operates around 10 flights from Chicago Midway Airport to San Antonio every week. The average price of these flights found in the last 72 hours has been $428, 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 8.0/10 in 4,237 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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