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Cheap flights from San Antonio to Chicago from $94

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 5/12. 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.
Multiple Airlines Logo
3:00 pm - 10:14 pm
SAT
-
MDW
31h 14m
2 stops
Multiple Airlines Logo
6:49 pm - 1:17 pm
MDW
-
SAT
18h 28m
1 stop
$235Multiple Airlines
Fri, Apr 17 - Fri, Apr 24
Multiple Airlines Logo
2:40 pm - 6:13 pm
SAT
-
MDW
27h 33m
1 stop
Multiple Airlines Logo
2:41 pm - 12:27 pm
MDW
-
SAT
21h 46m
2 stops
$254Multiple Airlines
Mon, Mar 16 - Mon, Mar 23
Frontier Logo
2:08 pm - 6:13 pm
SAT
-
MDW
28h 05m
1 stop
Frontier Logo
9:51 pm - 1:23 pm
MDW
-
SAT
15h 32m
1 stop
$259Frontier
Tue, Mar 17 - Mon, Mar 23
Multiple Airlines Logo
2:12 pm - 8:04 am
SAT
-
MDW
17h 52m
1 stop
Multiple Airlines Logo
2:15 pm - 9:24 am
MDW
-
SAT
19h 09m
2 stops
$260Multiple Airlines
Wed, Apr 15 - Thu, Apr 16
Multiple Airlines Logo
2:12 pm - 7:26 am
SAT
-
MDW
17h 14m
1 stop
Multiple Airlines Logo
2:15 pm - 3:53 pm
MDW
-
SAT
25h 38m
2 stops
$262Multiple Airlines
Wed, Apr 22 - Tue, Apr 28
Multiple Airlines Logo
6:54 pm - 8:04 am
SAT
-
MDW
13h 10m
1 stop
Multiple Airlines Logo
2:20 pm - 11:51 pm
MDW
-
SAT
9h 31m
2 stops
$263Multiple Airlines
Sat, May 9 - Wed, May 13
Multiple Airlines Logo
2:12 pm - 8:04 am
SAT
-
MDW
17h 52m
1 stop
Multiple Airlines Logo
2:15 pm - 11:51 pm
MDW
-
SAT
9h 36m
2 stops
$264Multiple Airlines
Wed, Apr 15 - Wed, Apr 22
Multiple Airlines Logo
10:22 am - 7:31 pm
SAT
-
MDW
9h 09m
2 stops
Multiple Airlines Logo
6:49 pm - 1:17 pm
MDW
-
SAT
18h 28m
1 stop
$265Multiple Airlines
Tue, Apr 14 - Fri, Apr 24
Multiple Airlines Logo
6:54 pm - 8:04 am
SAT
-
MDW
13h 10m
1 stop
Multiple Airlines Logo
2:20 pm - 1:17 pm
MDW
-
SAT
22h 57m
2 stops
$269Multiple Airlines
Sat, May 16 - Tue, May 19
Frontier Logo
2:13 pm - 3:33 pm
SAT
-
MDW
25h 20m
1 stop
Frontier Logo
6:00 am - 5:05 pm
MDW
-
SAT
11h 05m
1 stop
$270Frontier
Mon, Mar 30 - Mon, Apr 6

Southwest flights from San Antonio to Chicago Midway Airport

Our best Southwest deals on San Antonio to Chicago Midway Airport flight tickets
Southwest
Mar 31
SAT9:20 amSan Antonio
2h 30m
MDW11:50 amChicago Midway
Apr 7
MDW9:00 pmChicago Midway
2h 50m
SAT11:50 pmSan Antonio
$277
Southwest
Apr 22
SAT5:40 pmSan Antonio
4h 05m
1 stop
MDW9:45 pmChicago Midway
Apr 28
MDW9:00 pmChicago Midway
2h 50m
SAT11:50 pmSan Antonio
$283
Southwest
Mar 31
SAT9:20 amSan Antonio
2h 30m
MDW11:50 amChicago Midway
Apr 7
MDW12:20 pmChicago Midway
5h 00m
1 stop
SAT5:20 pmSan Antonio
$287

Frontier flights from San Antonio to Chicago Midway Airport

Our best Frontier deals on San Antonio to Chicago Midway Airport flight tickets
Frontier
Mar 17
SAT2:08 pmSan Antonio
28h 05m
1 stop
MDW6:13 pmChicago Midway
Mar 23
MDW9:51 pmChicago Midway
15h 32m
1 stop
SAT1:23 pmSan Antonio
$259
Frontier
Apr 18
SAT6:30 pmSan Antonio
13h 29m
1 stop
MDW7:59 amChicago Midway
Apr 20
MDW2:15 pmChicago Midway
49h 38m
2 stops
SAT3:53 pmSan Antonio
$261
Frontier
Mar 30
SAT2:13 pmSan Antonio
25h 20m
1 stop
MDW3:33 pmChicago Midway
Apr 6
MDW6:00 amChicago Midway
11h 05m
1 stop
SAT5:05 pmSan Antonio
$270

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 March 6, 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

Cheapest round-trip

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 4/17

3:00 pm-10:14 pm

2 stops31h 14m

Chicago Midway

Fri 4/24

6:49 pm-1:17 pm

1 stop18h 28m

$235

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Mon 3/16

2:40 pm-6:13 pm

1 stop27h 33m

Chicago Midway

Mon 3/23

2:41 pm-12:27 pm

2 stops21h 46m

$254

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Tue 3/17

2:08 pm-6:13 pm

1 stop28h 05m

Chicago Midway

Mon 3/23

9:51 pm-1:23 pm

1 stop15h 32m

$259

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 4/15

2:12 pm-8:04 am

1 stop17h 52m

Chicago Midway

Thu 4/16

2:15 pm-9:24 am

2 stops19h 09m

$260

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 4/22

2:12 pm-7:26 am

1 stop17h 14m

Chicago Midway

Tue 4/28

2:15 pm-3:53 pm

2 stops25h 38m

$262
Quickest round-trip

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 5/9

6:54 pm-8:04 am

1 stop13h 10m

Chicago Midway

Wed 5/13

2:20 pm-11:51 pm

2 stops9h 31m

$263

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 4/15

2:12 pm-8:04 am

1 stop17h 52m

Chicago Midway

Wed 4/22

2:15 pm-11:51 pm

2 stops9h 36m

$264

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Tue 4/14

10:22 am-7:31 pm

2 stops9h 09m

Chicago Midway

Fri 4/24

6:49 pm-1:17 pm

1 stop18h 28m

$265

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 5/16

6:54 pm-8:04 am

1 stop13h 10m

Chicago Midway

Tue 5/19

2:20 pm-1:17 pm

2 stops22h 57m

$269

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Mon 3/30

2:13 pm-3:33 pm

1 stop25h 20m

Chicago Midway

Mon 4/6

6:00 am-5:05 pm

1 stop11h 05m

$270

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 January is, on average, the cheapest month to fly to Chicago Midway Airport from San Antonio, with most prices found around $289. If you are unable to visit Chicago Midway Airport during the month of January, then departing from San Antonio during the month September is also very affordable. Most momondo users find prices during this month for around $296.

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 $379. 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 $366 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $437. 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 41% 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

$203

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 $203. The best round-trip flight deal from San Antonio to Chicago Midway Airport found on momondo in the last 72 hours is $368.
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 $156Free CancellationRating
5.7
3,041 reviews
Search Frontier flights
SouthwestPriceFrom $256Free CancellationRating
8.0
4,309 reviews
Search Southwest flights

  • Southwest Flights From San Antonio to Chicago Midway Airport

    Southwest flies from San Antonio to Chicago Midway Airport around 4 times per week, with 4,309 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 $400 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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Schererville
Munster
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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