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Cheap flights from San Antonio to Chicago from $78

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Antonio to Chicago departing on 3/2. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
5:04 pm - 10:25 pm
SAT
-
MDW
5h 21m1 stop
Frontier Logo
6:00 am - 4:18 pm
MDW
-
SAT
10h 18m1 stop
$217Frontier
Fri, Feb 20 - Mon, Feb 23
Frontier Logo
1:57 pm - 2:26 pm
SAT
-
MDW
24h 29m1 stop
Frontier Logo
7:30 am - 1:12 pm
MDW
-
SAT
29h 42m1 stop
$218Frontier
Thu, Feb 19 - Sun, Feb 22
Southwest Logo
6:00 am - 8:35 am
SAT
-
MDW
2h 35mnonstop
Southwest Logo
7:50 pm - 10:50 pm
MDW
-
SAT
3h 00mnonstop
$222Southwest
Sat, Jan 17 - Sat, Jan 24
Multiple Airlines Logo
6:18 pm - 12:05 pm
SAT
-
MDW
17h 47m1 stop
Multiple Airlines Logo
1:00 pm - 11:52 pm
MDW
-
SAT
10h 52m1 stop
$225Multiple Airlines
Mon, Jan 19 - Mon, Jan 26
Frontier Logo
10:13 am - 2:05 pm
SAT
-
MDW
27h 52m1 stop
Frontier Logo
4:21 pm - 7:03 pm
MDW
-
SAT
26h 42m1 stop
$231Frontier
Thu, Jan 8 - Sun, Jan 11
Southwest Logo
6:00 am - 8:35 am
SAT
-
MDW
2h 35mnonstop
Southwest Logo
8:20 am - 11:25 am
MDW
-
SAT
3h 05mnonstop
$238Southwest
Sat, Jan 17 - Sun, Jan 18
Multiple Airlines Logo
10:35 am - 7:52 pm
SAT
-
MDW
33h 17m2 stops
Multiple Airlines Logo
1:00 pm - 11:52 pm
MDW
-
SAT
10h 52m1 stop
$239Multiple Airlines
Thu, Jan 29 - Sun, Feb 1
Southwest Logo
5:20 am - 11:25 am
SAT
-
MDW
6h 05m1 stop
Southwest Logo
10:00 am - 3:35 pm
MDW
-
SAT
5h 35m1 stop
$241Southwest
Sat, Jan 17 - Sat, Jan 24
Southwest Logo
6:00 am - 8:35 am
SAT
-
MDW
2h 35mnonstop
Southwest Logo
6:15 am - 12:10 pm
MDW
-
SAT
5h 55m1 stop
$248Southwest
Sat, Jan 17 - Sun, Jan 18
Frontier Logo
11:17 am - 7:54 pm
SAT
-
MDW
8h 37m1 stop
Frontier Logo
8:28 am - 5:23 pm
MDW
-
SAT
8h 55m1 stop
$250Frontier
Fri, Jan 16 - Mon, Jan 19

Delta flights from San Antonio to Chicago Midway Airport

Our best Delta deals on San Antonio to Chicago Midway Airport flight tickets
Delta
Jan 13
SAT5:30 amSan Antonio
7h 18m
1 stop
MDW12:48 pmChicago Midway
Jan 17
MDW6:45 amChicago Midway
8h 36m
1 stop
SAT3:21 pmSan Antonio
$289
Find similar
Delta
Jan 1
SAT7:05 amSan Antonio
7h 39m
1 stop
MDW2:44 pmChicago Midway
Jan 12
MDW5:31 pmChicago Midway
5h 52m
1 stop
SAT11:23 pmSan Antonio
$346
Find similar
Delta
May 6
SAT5:10 amSan Antonio
7h 20m
1 stop
MDW12:30 pmChicago Midway
May 11
MDW5:59 pmChicago Midway
5h 13m
1 stop
SAT11:12 pmSan Antonio
$367
Find similar

Southwest flights from San Antonio to Chicago Midway Airport

Our best Southwest deals on San Antonio to Chicago Midway Airport flight tickets
Southwest
Jan 17
SAT6:00 amSan Antonio
2h 35m
MDW8:35 amChicago Midway
Jan 24
MDW7:50 pmChicago Midway
3h 00m
SAT10:50 pmSan Antonio
$222
Find similar
Southwest
Jan 17
SAT6:00 amSan Antonio
2h 35m
MDW8:35 amChicago Midway
Jan 18
MDW8:20 amChicago Midway
3h 05m
SAT11:25 amSan Antonio
$238
Find similar
Southwest
Jan 17
SAT5:20 amSan Antonio
6h 05m
1 stop
MDW11:25 amChicago Midway
Jan 24
MDW10:00 amChicago Midway
5h 35m
1 stop
SAT3:35 pmSan Antonio
$241
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from San Antonio to Chicago Midway Airport 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 23, 2025.
Use the filters below to find and compare flights from San Antonio to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 2/20

5:04 pm-10:25 pm

1 stop5h 21m

Chicago Midway

Mon 2/23

6:00 am-4:18 pm

1 stop10h 18m

$217

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 2/19

1:57 pm-2:26 pm

1 stop24h 29m

Chicago Midway

Sun 2/22

7:30 am-1:12 pm

1 stop29h 42m

$218

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 1/17

6:00 am-8:35 am

Nonstop2h 35m

Chicago Midway

Sat 1/24

7:50 pm-10:50 pm

Nonstop3h 00m

$222

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Mon 1/19

6:18 pm-12:05 pm

1 stop17h 47m

Chicago Midway

Mon 1/26

1:00 pm-11:52 pm

1 stop10h 52m

$225

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 1/8

10:13 am-2:05 pm

1 stop27h 52m

Chicago Midway

Sun 1/11

4:21 pm-7:03 pm

1 stop26h 42m

$231

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 1/17

6:00 am-8:35 am

Nonstop2h 35m

Chicago Midway

Sun 1/18

8:20 am-11:25 am

Nonstop3h 05m

$238

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 1/29

10:35 am-7:52 pm

2 stops33h 17m

Chicago Midway

Sun 2/1

1:00 pm-11:52 pm

1 stop10h 52m

$239

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 1/17

5:20 am-11:25 am

1 stop6h 05m

Chicago Midway

Sat 1/24

10:00 am-3:35 pm

1 stop5h 35m

$241

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 1/17

6:00 am-8:35 am

Nonstop2h 35m

Chicago Midway

Sun 1/18

6:15 am-12:10 pm

1 stop5h 55m

$248

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 1/16

11:17 am-7:54 pm

1 stop8h 37m

Chicago Midway

Mon 1/19

8:28 am-5:23 pm

1 stop8h 55m

$250

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 cheapest month to fly to Chicago Midway Airport?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from San Antonio, with most prices found around $296. If you are unable to visit Chicago Midway Airport during the month of September, then departing from San Antonio during the month October is also very affordable. Most momondo users find prices during this month for around $317.

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 $388. 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, Sunday 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 $446.

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

Flying to Chicago Midway Airport from San Antonio in the evening is the least expensive time of day to depart. momondo users have found prices as low as $237 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $438. 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 flights?

There is only 1 cabin class available to choose from on San Antonio to Chicago Midway 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 32% 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 December 2025, prices for San Antonio to Chicago Midway Airport flights are approximately 423% 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

$199

Fastest flight time

2h 35m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from San Antonio in the past 72 hours is $199. The best round-trip flight deal from San Antonio to Chicago Midway Airport found on momondo in the last 72 hours is $346.
The fastest flight from San Antonio to Chicago Midway Airport takes 2h 35m
Direct flights go from San Antonio to Chicago Midway Airport every day.
Search flight deals

  • 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 35m.

  • 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
FrontierPriceFrom $156Free CancellationRating
5.8
3,073 reviews
Search Frontier flights
SouthwestPriceFrom $256Free CancellationRating
8.0
4,256 reviews
Search Southwest flights

  • Southwest Flights From San Antonio to Chicago Midway Airport

    Southwest flies from San Antonio to Chicago Midway Airport around 12 times per week, with 4,256 momondo users rating the airline 8.0/10. The cheapest Southwest deal from San Antonio to Chicago Midway Airport in the last 72 hours was $256 (round-trip), much lower than the average airfare cost of $424 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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Hammond
Benton Harbor
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Portage
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Schererville
Munster
Crown Point
Chesterton
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Porter
Griffith
Saint John

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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