Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from San Antonio to Chicago from $129

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.
Southwest Logo
2:15 pm - 4:50 pmSAT  San Antonio-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
8:30 pm - 11:15 pmMDW  Chicago Midway-SAT San Antonio
2h 45mnonstop
$257Southwest
Mon, Sep 14 - Tue, Sep 15
Southwest Logo
2:15 pm - 4:50 pmSAT  San Antonio-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
10:10 am - 12:50 pmMDW  Chicago Midway-SAT San Antonio
2h 40mnonstop
$257Southwest
Mon, Sep 28 - Wed, Sep 30
Southwest Logo
5:00 am - 7:40 amSAT  San Antonio-MDW Chicago Midway
2h 40mnonstop
Southwest Logo
9:20 pm - 12:05 amMDW  Chicago Midway-SAT San Antonio
2h 45mnonstop
$257Southwest
Sat, Oct 3 - Mon, Oct 5
Southwest Logo
2:35 pm - 5:15 pmSAT  San Antonio-MDW Chicago Midway
2h 40mnonstop
Southwest Logo
9:30 pm - 12:20 amMDW  Chicago Midway-SAT San Antonio
2h 50mnonstop
$257Southwest
Thu, Oct 29 - Mon, Nov 2
Southwest Logo
2:50 pm - 5:25 pmSAT  San Antonio-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
10:10 am - 12:50 pmMDW  Chicago Midway-SAT San Antonio
2h 40mnonstop
$257Southwest
Tue, Sep 22 - Wed, Sep 30
Southwest Logo
5:00 am - 7:35 amSAT  San Antonio-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
1:55 pm - 5:55 pmMDW  Chicago Midway-SAT San Antonio
4h 00m1 stop Dallas Love Field
$263Southwest
Mon, Sep 14 - Tue, Sep 15
Southwest Logo
4:45 pm - 11:10 pmSAT  San Antonio-MDW Chicago Midway
6h 25m1 stop Atlanta Hartsfield-Jackson
Southwest Logo
9:30 pm - 12:20 amMDW  Chicago Midway-SAT San Antonio
2h 50mnonstop
$267Southwest
Thu, Oct 29 - Mon, Nov 2
Southwest Logo
9:20 am - 12:00 pmSAT  San Antonio-MDW Chicago Midway
2h 40mnonstop
Southwest Logo
4:30 pm - 11:00 pmMDW  Chicago Midway-SAT San Antonio
6h 30m1 stop Lambert-St Louis
$267Southwest
Mon, Oct 5 - Wed, Oct 7
JetBlue Logo
4:21 pm - 10:44 pmSAT  San Antonio-MDW Chicago Midway
6h 23m1 stop Atlanta Hartsfield-Jackson
JetBlue Logo
5:10 pm - 12:08 amMDW  Chicago Midway-SAT San Antonio
6h 58m1 stop Atlanta Hartsfield-Jackson
$271JetBlue
Fri, Sep 11 - Fri, Sep 18
Delta Logo
11:36 am - 4:57 pmSAT  San Antonio-MDW Chicago Midway
5h 21m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:10 pm - 12:08 amMDW  Chicago Midway-SAT San Antonio
6h 58m1 stop Atlanta Hartsfield-Jackson
$277Delta
Thu, Sep 10 - Mon, Sep 14

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Delta flights from San Antonio to Chicago Midway Airport

Our best Delta deals on San Antonio to Chicago Midway Airport flight tickets
Delta
Sep 10
SAT6:00 amSan Antonio
7h 20m
1 stop
MDW1:20 pmChicago Midway
Sep 14
MDW5:10 pmChicago Midway
6h 58m
1 stop
SAT12:08 amSan Antonio
$277
Delta
Nov 2
SAT5:30 amSan Antonio
5h 13m
1 stop
MDW10:43 amChicago Midway
Nov 5
MDW11:39 amChicago Midway
5h 35m
1 stop
SAT5:14 pmSan Antonio
$308
Delta
Dec 4
SAT11:45 amSan Antonio
6h 19m
1 stop
MDW6:04 pmChicago Midway
Dec 7
MDW5:09 pmChicago Midway
7h 22m
1 stop
SAT12:31 amSan Antonio
$319

Southwest flights from San Antonio to Chicago Midway Airport

Our best Southwest deals on San Antonio to Chicago Midway Airport flight tickets
Southwest
Sep 14
SAT2:15 pmSan Antonio
2h 35m
MDW4:50 pmChicago Midway
Sep 15
MDW8:30 pmChicago Midway
2h 45m
SAT11:15 pmSan Antonio
$257
Southwest
Sep 14
SAT5:00 amSan Antonio
2h 35m
MDW7:35 amChicago Midway
Sep 15
MDW1:55 pmChicago Midway
4h 00m
1 stop
SAT5:55 pmSan Antonio
$263
Southwest
Sep 10
SAT2:55 pmSan Antonio
6h 05m
1 stop
MDW9:00 pmChicago Midway
Sep 14
MDW8:35 pmChicago Midway
2h 45m
SAT11:20 pmSan Antonio
$267

momondo Fare Finder

 
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

Cheapest round-trip

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Mon 9/14

2:15 pm-4:50 pm

Nonstop2h 35m

Chicago Midway

Tue 9/15

8:30 pm-11:15 pm

Nonstop2h 45m

$257
Quickest round-trip

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Mon 9/28

2:15 pm-4:50 pm

Nonstop2h 35m

Chicago Midway

Wed 9/30

10:10 am-12:50 pm

Nonstop2h 40m

$257

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Sat 10/3

5:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Mon 10/5

9:20 pm-12:05 am

Nonstop2h 45m

$257

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Thu 10/29

2:35 pm-5:15 pm

Nonstop2h 40m

Chicago Midway

Mon 11/2

9:30 pm-12:20 am

Nonstop2h 50m

$257

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Tue 9/22

2:50 pm-5:25 pm

Nonstop2h 35m

Chicago Midway

Wed 9/30

10:10 am-12:50 pm

Nonstop2h 40m

$257

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Mon 9/14

5:00 am-7:35 am

Nonstop2h 35m

Chicago Midway

Tue 9/15

1:55 pm-5:55 pm

1 stop4h 00m

$263

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Thu 10/29

4:45 pm-11:10 pm

1 stop6h 25m

Chicago Midway

Mon 11/2

9:30 pm-12:20 am

Nonstop2h 50m

$267

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Mon 10/5

9:20 am-12:00 pm

Nonstop2h 40m

Chicago Midway

Wed 10/7

4:30 pm-11:00 pm

1 stop6h 30m

$267

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Fri 9/11

4:21 pm-10:44 pm

1 stop6h 23m

Chicago Midway

Fri 9/18

5:10 pm-12:08 am

1 stop6h 58m

$271

San AntonioChicago

SAT San Antonio - MDW Chicago Midway

SATMDW

San Antonio

Thu 9/10

11:36 am-4:57 pm

1 stop5h 21m

Chicago Midway

Mon 9/14

5:10 pm-12:08 am

1 stop6h 58m

$277

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $333 to $570.
The lowest price recently found on this route was $257.

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 $371. 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 $486.

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 $390 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $486. 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 55% 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 2026, prices for San Antonio to Chicago Midway Airport flights are approximately 275% 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

$129

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 $129. The best round-trip flight deal from San Antonio to Chicago Midway Airport found on momondo in the last 72 hours is $257.
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 $281Free CancellationRating
8.0
4,215 reviews
Search Southwest flights

  • Southwest Flights From San Antonio to Chicago Midway Airport

    Southwest flies from San Antonio to Chicago Midway Airport around 16 times per week, with 4,215 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 $281 (round-trip), much lower than the average airfare cost of $456 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
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 9/19
Sat 9/26
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago