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Cheap flights from San Antonio to Chicago from $64

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 2/20. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
4:29 pm - 10:07 pm
SAT
-
MDW
5h 38m1 stop
Delta Logo
6:25 am - 12:45 pm
MDW
-
SAT
6h 20m1 stop
$197Delta
Sat, Jan 17 - Sat, Jan 24
Delta Logo
5:20 am - 10:32 am
SAT
-
MDW
5h 12m1 stop
Delta Logo
1:49 pm - 9:34 pm
MDW
-
SAT
7h 45m1 stop
$199Delta
Sat, Jan 10 - Mon, Jan 12
Delta Logo
4:29 pm - 10:07 pm
SAT
-
MDW
5h 38m1 stop
Delta Logo
1:49 pm - 9:34 pm
MDW
-
SAT
7h 45m1 stop
$201Delta
Fri, Jan 9 - 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
$203Southwest
Sat, Jan 10 - Mon, Jan 12
Multiple Airlines Logo
10:35 am - 10:17 pm
SAT
-
MDW
11h 42m2 stops
Multiple Airlines Logo
4:21 pm - 11:52 pm
MDW
-
SAT
7h 31m1 stop
$204Multiple Airlines
Thu, Jan 8 - Sun, Jan 11
Frontier Logo
6:13 pm - 8:43 am
SAT
-
MDW
14h 30m1 stop
Frontier Logo
5:01 pm - 5:03 pm
MDW
-
SAT
24h 02m1 stop
$218Frontier
Fri, Feb 6 - Sun, Feb 8
Southwest Logo
8:20 am - 4:35 pm
SAT
-
MDW
8h 15m2 stops
Southwest Logo
9:45 am - 8:10 pm
MDW
-
SAT
10h 25m2 stops
$223Southwest
Tue, Feb 3 - Sat, Feb 7
Multiple Airlines Logo
10:35 am - 10:19 pm
SAT
-
MDW
11h 44m2 stops
Multiple Airlines Logo
6:20 am - 5:03 pm
MDW
-
SAT
10h 43m1 stop
$225Multiple Airlines
Fri, Jan 23 - Fri, Jan 30
Southwest Logo
6:15 am - 1:30 pm
SAT
-
MDW
7h 15m1 stop
Southwest Logo
8:20 am - 11:25 am
MDW
-
SAT
3h 05mnonstop
$227Southwest
Sat, Jan 10 - Mon, Jan 12
Multiple Airlines Logo
10:35 am - 10:19 pm
SAT
-
MDW
11h 44m2 stops
Multiple Airlines Logo
5:01 pm - 5:03 pm
MDW
-
SAT
24h 02m1 stop
$228Multiple Airlines
Thu, Jan 22 - Sun, Jan 25

Southwest flights from San Antonio to Chicago Midway Airport

Our best Southwest deals on San Antonio to Chicago Midway Airport flight tickets
Southwest
Jan 10
SAT6:00 amSan Antonio
2h 35m
MDW8:35 amChicago Midway
Jan 12
MDW8:20 amChicago Midway
3h 05m
SAT11:25 amSan Antonio
$203
Find similar
Southwest
Feb 3
SAT8:20 amSan Antonio
8h 15m
2 stops
MDW4:35 pmChicago Midway
Feb 7
MDW9:45 amChicago Midway
10h 25m
2 stops
SAT8:10 pmSan Antonio
$223
Find similar
Southwest
Jan 10
SAT6:15 amSan Antonio
7h 15m
1 stop
MDW1:30 pmChicago Midway
Jan 12
MDW8:20 amChicago Midway
3h 05m
SAT11:25 amSan Antonio
$227
Find similar

Frontier flights from San Antonio to Chicago Midway Airport

Our best Frontier deals on San Antonio to Chicago Midway Airport flight tickets
Frontier
Feb 6
SAT6:13 pmSan Antonio
14h 30m
1 stop
MDW8:43 amChicago Midway
Feb 8
MDW5:01 pmChicago Midway
24h 02m
1 stop
SAT5:03 pmSan Antonio
$218
Find similar
Frontier
Dec 11
SAT7:56 pmSan Antonio
15h 12m
1 stop
MDW11:08 amChicago Midway
Dec 15
MDW12:18 pmChicago Midway
6h 40m
1 stop
SAT6:58 pmSan Antonio
$225
Find similar
Frontier
Dec 30
SAT12:18 pmSan Antonio
7h 37m
1 stop
MDW7:55 pmChicago Midway
Jan 5
MDW6:12 amChicago Midway
10h 49m
1 stop
SAT5:01 pmSan Antonio
$233
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 4, 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

Sat 1/17

4:29 pm-10:07 pm

1 stop5h 38m

Chicago Midway

Sat 1/24

6:25 am-12:45 pm

1 stop6h 20m

$197

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 1/10

5:20 am-10:32 am

1 stop5h 12m

Chicago Midway

Mon 1/12

1:49 pm-9:34 pm

1 stop7h 45m

$199

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 1/9

4:29 pm-10:07 pm

1 stop5h 38m

Chicago Midway

Sun 1/11

1:49 pm-9:34 pm

1 stop7h 45m

$201

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 1/10

6:00 am-8:35 am

Nonstop2h 35m

Chicago Midway

Mon 1/12

8:20 am-11:25 am

Nonstop3h 05m

$203

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 1/8

10:35 am-10:17 pm

2 stops11h 42m

Chicago Midway

Sun 1/11

4:21 pm-11:52 pm

1 stop7h 31m

$204

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 2/6

6:13 pm-8:43 am

1 stop14h 30m

Chicago Midway

Sun 2/8

5:01 pm-5:03 pm

1 stop24h 02m

$218

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Tue 2/3

8:20 am-4:35 pm

2 stops8h 15m

Chicago Midway

Sat 2/7

9:45 am-8:10 pm

2 stops10h 25m

$223

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 1/23

10:35 am-10:19 pm

2 stops11h 44m

Chicago Midway

Fri 1/30

6:20 am-5:03 pm

1 stop10h 43m

$225

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 1/10

6:15 am-1:30 pm

1 stop7h 15m

Chicago Midway

Mon 1/12

8:20 am-11:25 am

Nonstop3h 05m

$227

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 1/22

10:35 am-10:19 pm

2 stops11h 44m

Chicago Midway

Sun 1/25

5:01 pm-5:03 pm

1 stop24h 02m

$228

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 $470.

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

$269

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 $269. The best round-trip flight deal from San Antonio to Chicago Midway Airport found on momondo in the last 72 hours is $425.
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

  • 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
3,092 reviews
Search Frontier flights
SouthwestPriceFrom $256Free CancellationRating
8.0
4,252 reviews
Search Southwest flights

  • Southwest Flights From San Antonio to Chicago Midway Airport

    Southwest flies from San Antonio to Chicago Midway Airport around 14 times per week, with 4,252 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 $425 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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Portage
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Valparaiso
Crown Point
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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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