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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 10/20. 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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Find the cheapest flights from Chicago Midway Airport to San Antonio (MDW-SAT)

Cheap round-trip flights

Frontier Logo
12:30 pm - 7:30 pmMDW-SAT
7h 00m1 stop
Frontier Logo
10:46 pm - 11:30 amSAT-MDW
12h 44m2 stops
$227Frontier
Find Deal
Fri, Oct 31 - Sun, Nov 2
Frontier Logo
6:20 am - 4:52 pmMDW-SAT
10h 32m1 stop
Frontier Logo
10:54 am - 9:46 pmSAT-MDW
10h 52m1 stop
$230Frontier
Find Deal
Sun, Oct 19 - Mon, Oct 20
Logo
12:11 pm - 7:41 pmMDW-SAT
7h 30m1 stop
Logo
2:42 pm - 11:38 amSAT-MDW
20h 56m2 stops
$244
Find Deal
Fri, Oct 24 - Mon, Oct 27
Logo
6:24 pm - 7:35 pmMDW-SAT
25h 11m1 stop
Logo
7:00 am - 1:38 pmSAT-MDW
30h 38m2 stops
$245
Find Deal
Thu, Oct 9 - Tue, Oct 14
Frontier Logo
9:47 pm - 2:27 pmMDW-SAT
16h 40m2 stops
Frontier Logo
8:20 pm - 12:44 pmSAT-MDW
16h 24m2 stops
$246Frontier
Find Deal
Fri, Sep 19 - Sun, Sep 21
Frontier Logo
6:20 am - 4:30 pmMDW-SAT
10h 10m1 stop
Frontier Logo
8:20 pm - 1:11 pmSAT-MDW
16h 51m2 stops
$249Frontier
Find Deal
Fri, Sep 19 - Sun, Sep 21
Southwest Logo
8:40 pm - 11:30 pmMDW-SAT
2h 50mnonstop
Southwest Logo
1:20 pm - 4:00 pmSAT-MDW
2h 40mnonstop
$302Southwest
Find Deal
Wed, Oct 29 - Fri, Oct 31
Southwest Logo
7:55 am - 10:55 amMDW-SAT
3h 00mnonstop
Southwest Logo
12:45 pm - 4:50 pmSAT-MDW
4h 05m1 stop
$303Southwest
Find Deal
Mon, Nov 10 - Tue, Nov 18
Delta Logo
5:04 pm - 12:20 amMDW-SAT
7h 16m1 stop
Delta Logo
6:25 am - 1:08 pmSAT-MDW
6h 43m1 stop
$307Delta
Find Deal
Tue, Oct 21 - Tue, Oct 28
Delta Logo
10:40 am - 5:16 pmMDW-SAT
6h 36m1 stop
Delta Logo
11:35 am - 6:25 pmSAT-MDW
6h 50m1 stop
$317Delta
Find Deal
Wed, Oct 29 - Mon, Nov 3

Frontier flights from Chicago Midway Airport to San Antonio

Our best Frontier deals on Chicago Midway Airport to San Antonio flight tickets
Frontier
Oct 31
MDW12:30 pmChicago Midway
7h 00m
1 stop
SAT7:30 pmSan Antonio
Nov 2
SAT10:46 pmSan Antonio
12h 44m
2 stops
MDW11:30 amChicago Midway
$227
Find similar
Frontier
Sep 12
MDW6:20 amChicago Midway
10h 10m
1 stop
SAT4:30 pmSan Antonio
Sep 15
SAT5:40 pmSan Antonio
5h 40m
1 stop
MDW11:20 pmChicago Midway
$229
Find similar
Frontier
Oct 19
MDW6:20 amChicago Midway
10h 32m
1 stop
SAT4:52 pmSan Antonio
Oct 20
SAT10:54 amSan Antonio
10h 52m
1 stop
MDW9:46 pmChicago Midway
$230
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
Oct 29
MDW8:40 pmChicago Midway
2h 50m
SAT11:30 pmSan Antonio
Oct 31
SAT1:20 pmSan Antonio
2h 40m
MDW4:00 pmChicago Midway
$302
Find similar
Southwest
Nov 10
MDW7:55 amChicago Midway
3h 00m
SAT10:55 amSan Antonio
Nov 18
SAT12:45 pmSan Antonio
4h 05m
1 stop
MDW4:50 pmChicago Midway
$303
Find similar
Southwest
Oct 29
MDW10:50 amChicago Midway
4h 55m
1 stop
SAT3:45 pmSan Antonio
Oct 31
SAT6:40 amSan Antonio
2h 35m
MDW9:15 amChicago Midway
$312
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 September 8, 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 10/31

12:30 pm-7:30 pm

1 stop7h 00m

San Antonio

Sun 11/2

10:46 pm-11:30 am

2 stops12h 44m

$227

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sun 10/19

6:20 am-4:52 pm

1 stop10h 32m

San Antonio

Mon 10/20

10:54 am-9:46 pm

1 stop10h 52m

$230

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Fri 10/24

12:11 pm-7:41 pm

1 stop7h 30m

San Antonio

Mon 10/27

2:42 pm-11:38 am

2 stops20h 56m

$244

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Thu 10/9

6:24 pm-7:35 pm

1 stop25h 11m

San Antonio

Tue 10/14

7:00 am-1:38 pm

2 stops30h 38m

$245

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Fri 9/19

9:47 pm-2:27 pm

2 stops16h 40m

San Antonio

Sun 9/21

8:20 pm-12:44 pm

2 stops16h 24m

$246

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Fri 9/19

6:20 am-4:30 pm

1 stop10h 10m

San Antonio

Sun 9/21

8:20 pm-1:11 pm

2 stops16h 51m

$249

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 10/29

8:40 pm-11:30 pm

Nonstop2h 50m

San Antonio

Fri 10/31

1:20 pm-4:00 pm

Nonstop2h 40m

$302

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Mon 11/10

7:55 am-10:55 am

Nonstop3h 00m

San Antonio

Tue 11/18

12:45 pm-4:50 pm

1 stop4h 05m

$303

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Tue 10/21

5:04 pm-12:20 am

1 stop7h 16m

San Antonio

Tue 10/28

6:25 am-1:08 pm

1 stop6h 43m

$307

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Wed 10/29

10:40 am-5:16 pm

1 stop6h 36m

San Antonio

Mon 11/3

11:35 am-6:25 pm

1 stop6h 50m

$317

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 $392. 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 $447.

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 $373. 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 $427. 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?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to San Antonio.

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

$315

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 $315. The best round-trip flight deal from Chicago Midway Airport to San Antonio found on momondo in the last 72 hours is $295.
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 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 $158Free CancellationRating
5.8
3,189 reviews
Search Frontier flights
SouthwestPriceFrom $232Free CancellationRating
8.0
4,247 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to San Antonio

    Southwest operates around 9 flights from Chicago Midway Airport to San Antonio every week. The average price of these flights found in the last 72 hours has been $413, but momondo users have found Southwest deals from Chicago Midway Airport to San Antonio from as low as $232 round-trip. Southwest has been scored 8.0/10 in 4,247 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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