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Cheap flights from San Antonio to Chicago from $118

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from San Antonio to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
12:06 pm - 7:47 pmSAT  San Antonio-MDW Chicago Midway
7h 41m1 stop Orlando
Frontier Logo
8:42 pm - 11:11 amMDW  Chicago Midway-SAT San Antonio
14h 29m1 stop Orlando
$307Frontier
Wed, Nov 25 - Sun, Nov 29
Southwest Logo
5:40 am - 2:50 pmSAT  San Antonio-MDW Chicago Midway
9h 10m2 stops Las Vegas Harry Reid Intl Des Moines
Southwest Logo
9:30 pm - 12:30 amMDW  Chicago Midway-SAT San Antonio
3h 00mnonstop
$308Southwest
Thu, Nov 26 - Mon, Nov 30
Southwest Logo
6:50 pm - 12:15 amSAT  San Antonio-MDW Chicago Midway
5h 25m1 stop Denver Intl
Southwest Logo
7:20 pm - 1:25 amMDW  Chicago Midway-SAT San Antonio
6h 05m1 stop Nashville Intl
$312Southwest
Wed, Nov 25 - Mon, Nov 30
Frontier Logo
12:06 pm - 7:47 pmSAT  San Antonio-MDW Chicago Midway
7h 41m1 stop Orlando
Frontier Logo
8:42 pm - 11:11 amMDW  Chicago Midway-SAT San Antonio
14h 29m1 stop Orlando
$313Frontier
Fri, Nov 20 - Tue, Nov 24
Frontier Logo
11:55 am - 7:42 pmSAT  San Antonio-MDW Chicago Midway
7h 47m1 stop Orlando
Frontier Logo
8:47 pm - 11:00 amMDW  Chicago Midway-SAT San Antonio
14h 13m1 stop Orlando
$318Frontier
Fri, Jan 22 - Sun, Jan 24
Frontier Logo
12:06 pm - 7:47 pmSAT  San Antonio-MDW Chicago Midway
7h 41m1 stop Orlando
Frontier Logo
8:42 pm - 11:11 amMDW  Chicago Midway-SAT San Antonio
14h 29m1 stop Orlando
$318Frontier
Fri, Nov 20 - Tue, Nov 24
Southwest Logo
5:30 am - 12:30 pmSAT  San Antonio-MDW Chicago Midway
7h 00m2 stops Dallas Love Field Omaha Eppley Airfield
Southwest Logo
7:20 pm - 1:25 amMDW  Chicago Midway-SAT San Antonio
6h 05m1 stop Nashville Intl
$318Southwest
Thu, Nov 26 - Mon, Nov 30
Frontier Logo
1:32 pm - 2:41 pmSAT  San Antonio-MDW Chicago Midway
25h 09m1 stop Orlando
Frontier Logo
8:37 pm - 11:40 amMDW  Chicago Midway-SAT San Antonio
15h 03m1 stop Orlando
$350Frontier
Wed, Dec 2 - Sun, Dec 6
Southwest Logo
7:00 am - 9:35 amSAT  San Antonio-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
9:30 pm - 12:30 amMDW  Chicago Midway-SAT San Antonio
3h 00mnonstop
$356Southwest
Sat, Dec 12 - Wed, Dec 30
Frontier Logo
11:55 am - 7:42 pmSAT  San Antonio-MDW Chicago Midway
7h 47m1 stop Orlando
Frontier Logo
8:47 pm - 11:00 amMDW  Chicago Midway-SAT San Antonio
14h 13m1 stop Orlando
$358Frontier
Fri, Jan 29 - Sun, Jan 31

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Frontier flights from San Antonio to Chicago Midway Airport

Our best Frontier deals on San Antonio to Chicago Midway Airport flight tickets
Frontier
Nov 25
SAT12:06 pmSan Antonio
7h 41m
1 stop
MDW7:47 pmChicago Midway
Nov 29
MDW8:42 pmChicago Midway
14h 29m
1 stop
SAT11:11 amSan Antonio
$307
Frontier
Nov 20
SAT12:06 pmSan Antonio
7h 41m
1 stop
MDW7:47 pmChicago Midway
Nov 24
MDW8:42 pmChicago Midway
14h 29m
1 stop
SAT11:11 amSan Antonio
$313
Frontier
Jan 22
SAT11:55 amSan Antonio
7h 47m
1 stop
MDW7:42 pmChicago Midway
Jan 24
MDW8:47 pmChicago Midway
14h 13m
1 stop
SAT11:00 amSan Antonio
$318

Southwest flights from San Antonio to Chicago Midway Airport

Our best Southwest deals on San Antonio to Chicago Midway Airport flight tickets
Southwest
Nov 26
SAT5:40 amSan Antonio
9h 10m
2 stops
MDW2:50 pmChicago Midway
Nov 30
MDW9:30 pmChicago Midway
3h 00m
SAT12:30 amSan Antonio
$308
Southwest
Nov 25
SAT6:50 pmSan Antonio
5h 25m
1 stop
MDW12:15 amChicago Midway
Nov 30
MDW7:20 pmChicago Midway
6h 05m
1 stop
SAT1:25 amSan Antonio
$312
Southwest
Nov 27
SAT11:25 amSan Antonio
6h 25m
1 stop
MDW5:50 pmChicago Midway
Dec 1
MDW8:50 pmChicago Midway
2h 55m
SAT11:45 pmSan Antonio
$341

momondo Fare Finder

 
Use the filters below to find and compare flights from San Antonio to Chicago Midway Airport that are best for you.

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Route

Depart

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Price

Cheapest round-trip

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Wed 11/25

12:06 pm-7:47 pm

1 stop7h 41m

Chicago Midway

Sun 11/29

8:42 pm-11:11 am

1 stop14h 29m

$307

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Thu 11/26

5:40 am-2:50 pm

2 stops9h 10m

Chicago Midway

Mon 11/30

9:30 pm-12:30 am

Nonstop3h 00m

$308

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Wed 11/25

6:50 pm-12:15 am

1 stop5h 25m

Chicago Midway

Mon 11/30

7:20 pm-1:25 am

1 stop6h 05m

$312

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Fri 11/20

12:06 pm-7:47 pm

1 stop7h 41m

Chicago Midway

Tue 11/24

8:42 pm-11:11 am

1 stop14h 29m

$313

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Fri 1/22

11:55 am-7:42 pm

1 stop7h 47m

Chicago Midway

Sun 1/24

8:47 pm-11:00 am

1 stop14h 13m

$318

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Fri 11/20

12:06 pm-7:47 pm

1 stop7h 41m

Chicago Midway

Tue 11/24

8:42 pm-11:11 am

1 stop14h 29m

$318

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Thu 11/26

5:30 am-12:30 pm

2 stops7h 00m

Chicago Midway

Mon 11/30

7:20 pm-1:25 am

1 stop6h 05m

$318

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Wed 12/2

1:32 pm-2:41 pm

1 stop25h 09m

Chicago Midway

Sun 12/6

8:37 pm-11:40 am

1 stop15h 03m

$350
Quickest round-trip

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Sat 12/12

7:00 am-9:35 am

Nonstop2h 35m

Chicago Midway

Wed 12/30

9:30 pm-12:30 am

Nonstop3h 00m

$356

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Fri 1/29

11:55 am-7:42 pm

1 stop7h 47m

Chicago Midway

Sun 1/31

8:47 pm-11:00 am

1 stop14h 13m

$358

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 Chicago from

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

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 typical price of a round-trip flight between San Antonio and Chicago Midway Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $444 to $650.
The lowest price recently found on this route was $307.

What is the cheapest month to fly to Chicago Midway Airport?

The month of April is, on average, the cheapest month to fly to Chicago Midway Airport from San Antonio, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of April, then departing from San Antonio during the month February is also very affordable. Most momondo users find prices during this month for around $260.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from San Antonio. The lowest ticket price found for a Wednesday departure recently was $374. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Friday is the most expensive day to depart from San Antonio because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $492.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from San Antonio at noon is the least expensive time of day to depart. momondo users have found prices as low as $400 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $519. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

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

There is only 1 cabin class available to choose from on San Antonio to Chicago Midway Airport 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 San Antonio to Chicago Midway Airport flights?

You could potentially save up to 1% on your flight if you consider stops on a San Antonio to Chicago Midway Airport flight.

How have San Antonio to Chicago Midway Airport flight prices changed over time?

As of October 2026, prices for San Antonio to Chicago Midway Airport flights are approximately 89% more expensive when compared to flights at the same time last year.

When to book flights from San Antonio to Chicago Midway Airport

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

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

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

Best Price Found

$118

Fastest flight time

2h 30m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from San Antonio in the past 72 hours is $118. The best round-trip flight deal from San Antonio to Chicago Midway Airport found on momondo in the last 72 hours is $307.
The fastest flight from San Antonio to Chicago Midway Airport takes 2h 30m
Direct flights go from San Antonio to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from San Antonio to Chicago Midway Airport

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

    The straight-line distance from San Antonio to Chicago Midway is 1043.4 mi. By plane, this route typically takes 2h 30m.

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

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

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San Antonio Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

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

Best airlines flying from San Antonio to Chicago Midway Airport

Compare and see reviews for airlines that fly from San Antonio to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $315Free CancellationRating
7.9
4,209 reviews
Search Southwest flights

  • Southwest Flights From San Antonio to Chicago Midway Airport

    Southwest flies from San Antonio to Chicago Midway Airport around 11 times per week, with 4,209 momondo users rating the airline 7.9/10. The cheapest Southwest deal from San Antonio to Chicago Midway Airport in the last 72 hours was $315 (round-trip), much lower than the average airfare cost of $482 for Southwest flights on this route.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from San Antonio to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. momondo allows you to filter the results for San Antonio to Chicago flights to just show those with flexible booking policies.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from San Antonio.

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

Yes. momondo can track prices for San Antonio to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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