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Cheap flights from San Antonio to Chicago from $73

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 9/15. 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 San Antonio to Chicago (SAT-MDW)

Cheap round-trip flights

Frontier Logo
5:45 pm - 11:25 pmSAT-MDW
5h 40m1 stop
Frontier Logo
6:20 am - 4:50 pmMDW-SAT
10h 30m1 stop
$144Frontier
Find Deal
Fri, Oct 17 - Mon, Oct 20
Frontier Logo
12:09 pm - 12:36 amSAT-MDW
12h 27m1 stop
Frontier Logo
6:20 am - 4:50 pmMDW-SAT
10h 30m1 stop
$157Frontier
Find Deal
Sun, Oct 12 - Sun, Oct 19
Frontier Logo
5:45 pm - 11:25 pmSAT-MDW
5h 40m1 stop
Frontier Logo
9:26 pm - 4:50 pmMDW-SAT
19h 24m1 stop
$166Frontier
Find Deal
Fri, Oct 24 - Sun, Oct 26
Frontier Logo
12:09 pm - 12:36 amSAT-MDW
12h 27m1 stop
Frontier Logo
9:44 am - 4:50 pmMDW-SAT
7h 06m1 stop
$184Frontier
Find Deal
Thu, Oct 16 - Fri, Oct 24
Logo
12:45 pm - 9:51 amSAT-MDW
21h 06m1 stop
Logo
10:13 am - 11:40 amMDW-SAT
25h 27m1 stop
$245
Find Deal
Fri, Sep 19 - Sun, Sep 28
Southwest Logo
2:40 pm - 5:15 pmSAT-MDW
2h 35mnonstop
Southwest Logo
8:25 am - 11:10 amMDW-SAT
2h 45mnonstop
$257Southwest
Find Deal
Wed, Sep 3 - Wed, Sep 10
Southwest Logo
6:30 am - 9:05 amSAT-MDW
2h 35mnonstop
Southwest Logo
12:50 pm - 6:15 pmMDW-SAT
5h 25m1 stop
$267Southwest
Find Deal
Wed, Sep 3 - Wed, Sep 10
Delta Logo
5:10 am - 12:28 pmSAT-MDW
7h 18m1 stop
Delta Logo
9:20 am - 5:15 pmMDW-SAT
7h 55m1 stop
$277Delta
Find Deal
Wed, Sep 17 - Tue, Sep 23
Logo
7:10 pm - 10:21 amSAT-MDW
15h 11m1 stop
Logo
12:09 pm - 4:55 amMDW-SAT
16h 46m2 stops
$286
Find Deal
Fri, Oct 17 - Sun, Oct 19
Delta Logo
2:00 pm - 9:36 pmSAT-MDW
7h 36m1 stop
Delta Logo
6:15 pm - 11:25 pmMDW-SAT
5h 10m1 stop
$297Delta
Find Deal
Wed, Sep 17 - Mon, Sep 22

Delta flights from San Antonio to Chicago Midway Airport

Our best Delta deals on San Antonio to Chicago Midway Airport flight tickets
Delta
Sep 17
SAT5:10 amSan Antonio
7h 18m
1 stop
MDW12:28 pmChicago Midway
Sep 23
MDW9:20 amChicago Midway
7h 55m
1 stop
SAT5:15 pmSan Antonio
$277
Find similar
Delta
Sep 17
SAT2:00 pmSan Antonio
7h 36m
1 stop
MDW9:36 pmChicago Midway
Sep 22
MDW6:15 pmChicago Midway
5h 10m
1 stop
SAT11:25 pmSan Antonio
$297
Find similar
Delta
Oct 27
SAT6:15 pmSan Antonio
23h 28m
1 stop
MDW5:43 pmChicago Midway
Nov 5
MDW6:00 amChicago Midway
7h 28m
1 stop
SAT1:28 pmSan Antonio
$311
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
Sep 3
SAT2:40 pmSan Antonio
2h 35m
MDW5:15 pmChicago Midway
Sep 10
MDW8:25 amChicago Midway
2h 45m
SAT11:10 amSan Antonio
$257
Find similar
Southwest
Sep 3
SAT6:30 amSan Antonio
2h 35m
MDW9:05 amChicago Midway
Sep 10
MDW12:50 pmChicago Midway
5h 25m
1 stop
SAT6:15 pmSan Antonio
$267
Find similar
Southwest
Sep 3
SAT11:00 amSan Antonio
6h 15m
2 stops
MDW5:15 pmChicago Midway
Sep 10
MDW8:25 amChicago Midway
2h 45m
SAT11:10 amSan Antonio
$272
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 August 14, 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 10/17

5:45 pm-11:25 pm

1 stop5h 40m

Chicago Midway

Mon 10/20

6:20 am-4:50 pm

1 stop10h 30m

$144

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sun 10/12

12:09 pm-12:36 am

1 stop12h 27m

Chicago Midway

Sun 10/19

6:20 am-4:50 pm

1 stop10h 30m

$157

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 10/24

5:45 pm-11:25 pm

1 stop5h 40m

Chicago Midway

Sun 10/26

9:26 pm-4:50 pm

1 stop19h 24m

$166

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 10/16

12:09 pm-12:36 am

1 stop12h 27m

Chicago Midway

Fri 10/24

9:44 am-4:50 pm

1 stop7h 06m

$184

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 9/19

12:45 pm-9:51 am

1 stop21h 06m

Chicago Midway

Sun 9/28

10:13 am-11:40 am

1 stop25h 27m

$245

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 9/3

2:40 pm-5:15 pm

Nonstop2h 35m

Chicago Midway

Wed 9/10

8:25 am-11:10 am

Nonstop2h 45m

$257

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 9/3

6:30 am-9:05 am

Nonstop2h 35m

Chicago Midway

Wed 9/10

12:50 pm-6:15 pm

1 stop5h 25m

$267

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 9/17

5:10 am-12:28 pm

1 stop7h 18m

Chicago Midway

Tue 9/23

9:20 am-5:15 pm

1 stop7h 55m

$277

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 10/17

7:10 pm-10:21 am

1 stop15h 11m

Chicago Midway

Sun 10/19

12:09 pm-4:55 am

2 stops16h 46m

$286

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 9/17

2:00 pm-9:36 pm

1 stop7h 36m

Chicago Midway

Mon 9/22

6:15 pm-11:25 pm

1 stop5h 10m

$297

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 October is, on average, the cheapest month to fly to Chicago Midway Airport from San Antonio, with most prices found around $340. If you are unable to visit Chicago Midway Airport during the month of October, then departing from San Antonio during the month May is also very affordable. Most momondo users find prices during this month for around $367.

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

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from San Antonio. The lowest ticket price found for a Tuesday departure recently was $391. 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 $436.

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 $436. 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 are 1 cabin classes 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 28% 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 August 2025, prices for San Antonio to Chicago Midway Airport flights are approximately 30% 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

$73

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 $73. The best round-trip flight deal from San Antonio to Chicago Midway Airport found on momondo in the last 72 hours is $144.
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 $147Free CancellationRating
5.8
3,219 reviews
Search Frontier flights
SouthwestPriceFrom $245Free CancellationRating
8.0
4,244 reviews
Search Southwest flights

  • Southwest Flights From San Antonio to Chicago Midway Airport

    Southwest flies from San Antonio to Chicago Midway Airport around 10 times per week, with 4,244 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 $245 (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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Hammond
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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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