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Cheap flights from San Antonio to Chicago 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 San Antonio to Chicago departing on 2/23. 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 - 7:07 pm
SAT
-
MDW
26h 03m
1 stop
Frontier Logo
6:00 am - 7:01 pm
MDW
-
SAT
13h 01m
2 stops
$216Frontier
Mon, Feb 16 - Sat, Feb 21
Frontier Logo
5:04 pm - 7:07 pm
SAT
-
MDW
26h 03m
1 stop
Frontier Logo
5:16 pm - 1:12 pm
MDW
-
SAT
19h 56m
2 stops
$223Frontier
Mon, Feb 23 - Thu, Feb 26
Multiple Airlines Logo
10:35 am - 10:19 pm
SAT
-
MDW
11h 44m
2 stops
Multiple Airlines Logo
6:20 am - 5:03 pm
MDW
-
SAT
10h 43m
1 stop
$244Multiple Airlines
Fri, Feb 6 - Sun, Feb 8
Multiple Airlines Logo
6:30 am - 11:45 am
SAT
-
MDW
29h 15m
2 stops
Multiple Airlines Logo
6:20 am - 5:03 pm
MDW
-
SAT
10h 43m
1 stop
$247Multiple Airlines
Wed, Feb 4 - Sun, Feb 8
Frontier Logo
5:04 pm - 10:25 pm
SAT
-
MDW
5h 21m
1 stop
Frontier Logo
6:00 am - 4:19 pm
MDW
-
SAT
10h 19m
1 stop
$250Frontier
Fri, Feb 20 - Sun, Feb 22
Multiple Airlines Logo
6:30 am - 11:45 am
SAT
-
MDW
29h 15m
2 stops
Multiple Airlines Logo
6:20 am - 5:03 pm
MDW
-
SAT
10h 43m
1 stop
$251Multiple Airlines
Wed, Feb 4 - Fri, Feb 6
Frontier Logo
6:12 pm - 1:56 pm
SAT
-
MDW
19h 44m
2 stops
Frontier Logo
6:00 am - 2:41 pm
MDW
-
SAT
8h 41m
1 stop
$254Frontier
Wed, Mar 4 - Mon, Mar 9
Multiple Airlines Logo
10:35 am - 8:43 am
SAT
-
MDW
22h 08m
2 stops
Multiple Airlines Logo
6:20 am - 5:03 pm
MDW
-
SAT
10h 43m
1 stop
$266Multiple Airlines
Fri, Feb 6 - Mon, Feb 9
Multiple Airlines Logo
6:00 am - 2:55 pm
SAT
-
MDW
8h 55m
1 stop
Multiple Airlines Logo
2:19 pm - 11:59 pm
MDW
-
SAT
9h 40m
2 stops
$267Multiple Airlines
Sat, Feb 21 - Mon, Feb 23
Frontier Logo
8:22 pm - 3:19 pm
SAT
-
MDW
18h 57m
2 stops
Frontier Logo
6:00 am - 4:19 pm
MDW
-
SAT
10h 19m
1 stop
$272Frontier
Fri, Feb 27 - Sun, Mar 1

Southwest flights from San Antonio to Chicago Midway Airport

Our best Southwest deals on San Antonio to Chicago Midway Airport flight tickets
Southwest
Feb 17
SAT2:40 pmSan Antonio
2h 35m
MDW5:15 pmChicago Midway
Feb 24
MDW11:30 amChicago Midway
7h 50m
1 stop
SAT7:20 pmSan Antonio
$285
Southwest
Feb 28
SAT5:30 amSan Antonio
7h 50m
1 stop
MDW1:20 pmChicago Midway
Feb 28
MDW5:50 pmChicago Midway
4h 50m
1 stop
SAT10:40 pmSan Antonio
$295
Southwest
Mar 3
SAT2:10 pmSan Antonio
2h 35m
MDW4:45 pmChicago Midway
Mar 9
MDW9:55 pmChicago Midway
2h 55m
SAT12:50 amSan Antonio
$304

Frontier flights from San Antonio to Chicago Midway Airport

Our best Frontier deals on San Antonio to Chicago Midway Airport flight tickets
Frontier
Feb 16
SAT5:04 pmSan Antonio
26h 03m
1 stop
MDW7:07 pmChicago Midway
Feb 21
MDW6:00 amChicago Midway
13h 01m
2 stops
SAT7:01 pmSan Antonio
$216
Frontier
Feb 23
SAT5:04 pmSan Antonio
26h 03m
1 stop
MDW7:07 pmChicago Midway
Feb 26
MDW5:16 pmChicago Midway
19h 56m
2 stops
SAT1:12 pmSan Antonio
$223
Frontier
Feb 20
SAT5:04 pmSan Antonio
5h 21m
1 stop
MDW10:25 pmChicago Midway
Feb 22
MDW6:00 amChicago Midway
10h 19m
1 stop
SAT4:19 pmSan Antonio
$250

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 January 21, 2026.
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

Mon 2/16

5:04 pm-7:07 pm

1 stop26h 03m

Chicago Midway

Sat 2/21

6:00 am-7:01 pm

2 stops13h 01m

$216

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Mon 2/23

5:04 pm-7:07 pm

1 stop26h 03m

Chicago Midway

Thu 2/26

5:16 pm-1:12 pm

2 stops19h 56m

$223

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 2/6

10:35 am-10:19 pm

2 stops11h 44m

Chicago Midway

Sun 2/8

6:20 am-5:03 pm

1 stop10h 43m

$244

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 2/4

6:30 am-11:45 am

2 stops29h 15m

Chicago Midway

Sun 2/8

6:20 am-5:03 pm

1 stop10h 43m

$247

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 2/20

5:04 pm-10:25 pm

1 stop5h 21m

Chicago Midway

Sun 2/22

6:00 am-4:19 pm

1 stop10h 19m

$250

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 2/4

6:30 am-11:45 am

2 stops29h 15m

Chicago Midway

Fri 2/6

6:20 am-5:03 pm

1 stop10h 43m

$251

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 3/4

6:12 pm-1:56 pm

2 stops19h 44m

Chicago Midway

Mon 3/9

6:00 am-2:41 pm

1 stop8h 41m

$254

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 2/6

10:35 am-8:43 am

2 stops22h 08m

Chicago Midway

Mon 2/9

6:20 am-5:03 pm

1 stop10h 43m

$266

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 2/21

6:00 am-2:55 pm

1 stop8h 55m

Chicago Midway

Mon 2/23

2:19 pm-11:59 pm

2 stops9h 40m

$267

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 2/27

8:22 pm-3:19 pm

2 stops18h 57m

Chicago Midway

Sun 3/1

6:00 am-4:19 pm

1 stop10h 19m

$272

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 $387. 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 $437.

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 $367 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $435. 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 59% 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?

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

$266

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 $266. The best round-trip flight deal from San Antonio to Chicago Midway Airport found on momondo in the last 72 hours is $332.
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 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
FrontierPriceFrom $141Free CancellationRating
5.7
3,057 reviews
Search Frontier flights
SouthwestPriceFrom $256Free CancellationRating
8.0
4,266 reviews
Search Southwest flights

  • Southwest Flights From San Antonio to Chicago Midway Airport

    Southwest flies from San Antonio to Chicago Midway Airport around 7 times per week, with 4,266 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 $418 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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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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