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Cheap flights from San Antonio to Chicago from $137

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 4/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:30 pm - 7:59 am
SAT
-
MDW
13h 29m
1 stop
Frontier Logo
6:20 am - 3:09 pm
MDW
-
SAT
32h 49m
2 stops
$256Frontier
sam., avr. 18 - lun., avr. 27
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
$260Frontier
lun., mars 30 - ven., avr. 3
Southwest Logo
7:15 am - 9:50 am
SAT
-
MDW
2h 35mnonstop
Southwest Logo
9:40 pm - 12:30 am
MDW
-
SAT
2h 50mnonstop
$283Southwest
sam., avr. 25 - lun., avr. 27
Multiple Airlines Logo
10:22 am - 10:19 pm
SAT
-
MDW
11h 57m
2 stops
Multiple Airlines Logo
6:00 am - 5:05 pm
MDW
-
SAT
11h 05m
1 stop
$289Multiple Airlines
mer., avr. 8 - lun., avr. 13
Multiple Airlines Logo
2:12 pm - 8:04 am
SAT
-
MDW
17h 52m
1 stop
Multiple Airlines Logo
2:15 pm - 2:15 pm
MDW
-
SAT
24h 00m
2 stops
$290Multiple Airlines
mer., avr. 15 - mer., avr. 22
Multiple Airlines Logo
2:12 pm - 7:26 am
SAT
-
MDW
17h 14m
1 stop
Multiple Airlines Logo
6:00 am - 6:59 pm
MDW
-
SAT
12h 59m
2 stops
$291Multiple Airlines
mer., avr. 22 - mer., mai 6
Southwest Logo
5:55 am - 1:10 pm
SAT
-
MDW
7h 15m
1 stop
Southwest Logo
9:40 pm - 12:30 am
MDW
-
SAT
2h 50mnonstop
$293Southwest
sam., avr. 25 - lun., avr. 27
Southwest Logo
9:05 am - 11:40 am
SAT
-
MDW
2h 35mnonstop
Southwest Logo
9:00 pm - 11:50 pm
MDW
-
SAT
2h 50mnonstop
$297Southwest
mar., avr. 14 - mer., avr. 15
Southwest Logo
7:15 am - 9:50 am
SAT
-
MDW
2h 35mnonstop
Southwest Logo
9:00 pm - 11:50 pm
MDW
-
SAT
2h 50mnonstop
$303Southwest
sam., avr. 25 - mar., avr. 28
Multiple Airlines Logo
1:22 pm - 10:19 pm
SAT
-
MDW
32h 57m
2 stops
Multiple Airlines Logo
5:01 am - 12:27 pm
MDW
-
SAT
7h 26m
1 stop
$305Multiple Airlines
mar., avr. 7 - jeu., avr. 9

Frontier flights from San Antonio to Chicago Midway Airport

Our best Frontier deals on San Antonio to Chicago Midway Airport flight tickets
Frontier
Apr 18
SAT6:30 pmSan Antonio
13h 29m
1 stop
MDW7:59 amChicago Midway
Apr 27
MDW6:20 amChicago Midway
32h 49m
2 stops
SAT3:09 pmSan Antonio
$256
Frontier
Mar 30
SAT2:13 pmSan Antonio
25h 20m
1 stop
MDW3:33 pmChicago Midway
Apr 3
MDW6:00 amChicago Midway
11h 05m
1 stop
SAT5:05 pmSan Antonio
$260
Frontier
May 4
SAT6:31 pmSan Antonio
40h 38m
2 stops
MDW11:09 amChicago Midway
May 11
MDW6:00 amChicago Midway
38h 14m
2 stops
SAT8:14 pmSan Antonio
$306

Southwest flights from San Antonio to Chicago Midway Airport

Our best Southwest deals on San Antonio to Chicago Midway Airport flight tickets
Southwest
Apr 25
SAT7:15 amSan Antonio
2h 35m
MDW9:50 amChicago Midway
Apr 27
MDW9:40 pmChicago Midway
2h 50m
SAT12:30 amSan Antonio
$283
Southwest
Apr 25
SAT5:55 amSan Antonio
7h 15m
1 stop
MDW1:10 pmChicago Midway
Apr 27
MDW9:40 pmChicago Midway
2h 50m
SAT12:30 amSan Antonio
$293
Southwest
Apr 22
SAT2:35 pmSan Antonio
2h 35m
MDW5:10 pmChicago Midway
May 6
MDW9:00 pmChicago Midway
2h 50m
SAT11:50 pmSan Antonio
$297

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 mars 23, 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

sam. 4/18

6:30 pm-7:59 am

1 stop13h 29m

Chicago Midway

lun. 4/27

6:20 am-3:09 pm

2 stops32h 49m

$256

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

lun. 3/30

2:13 pm-3:33 pm

1 stop25h 20m

Chicago Midway

ven. 4/3

6:00 am-5:05 pm

1 stop11h 05m

$260
Quickest round-trip

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

sam. 4/25

7:15 am-9:50 am

Nonstop2h 35m

Chicago Midway

lun. 4/27

9:40 pm-12:30 am

Nonstop2h 50m

$283

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

mer. 4/8

10:22 am-10:19 pm

2 stops11h 57m

Chicago Midway

lun. 4/13

6:00 am-5:05 pm

1 stop11h 05m

$289

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

mer. 4/15

2:12 pm-8:04 am

1 stop17h 52m

Chicago Midway

mer. 4/22

2:15 pm-2:15 pm

2 stops24h 00m

$290

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

mer. 4/22

2:12 pm-7:26 am

1 stop17h 14m

Chicago Midway

mer. 5/6

6:00 am-6:59 pm

2 stops12h 59m

$291

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

sam. 4/25

5:55 am-1:10 pm

1 stop7h 15m

Chicago Midway

lun. 4/27

9:40 pm-12:30 am

Nonstop2h 50m

$293

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

mar. 4/14

9:05 am-11:40 am

Nonstop2h 35m

Chicago Midway

mer. 4/15

9:00 pm-11:50 pm

Nonstop2h 50m

$297

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

sam. 4/25

7:15 am-9:50 am

Nonstop2h 35m

Chicago Midway

mar. 4/28

9:00 pm-11:50 pm

Nonstop2h 50m

$303

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

mar. 4/7

1:22 pm-10:19 pm

2 stops32h 57m

Chicago Midway

jeu. 4/9

5:01 am-12:27 pm

1 stop7h 26m

$305

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 February is, on average, the cheapest month to fly to Chicago Midway Airport from San Antonio, with most prices found around $260. If you are unable to visit Chicago Midway Airport during the month of February, then departing from San Antonio during the month January is also very affordable. Most momondo users find prices during this month for around $289.

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 $381. 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, Monday 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 $447.

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 $365 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $463. 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.

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 $369.
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
3,020 reviews
Search Frontier flights
SouthwestPriceFrom $256Free CancellationRating
8.0
4,324 reviews
Search Southwest flights

  • Southwest Flights From San Antonio to Chicago Midway Airport

    Southwest flies from San Antonio to Chicago Midway Airport around 13 times per week, with 4,324 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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Benton Harbor
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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