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Cheap flights from San Antonio to Chicago from $86

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 10/16. 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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Cheap round-trip flights

Frontier Logo
5:45 pm - 11:46 pmSAT-MDW
6h 01m1 stop
Frontier Logo
6:20 am - 4:52 pmMDW-SAT
10h 32m1 stop
$167Frontier
Find Deal
Fri, Oct 17 - Sun, Oct 19
Southwest Logo
7:25 pm - 12:05 amSAT-MDW
4h 40m1 stop
Southwest Logo
6:30 am - 10:40 amMDW-SAT
4h 10m1 stop
$173Southwest
Find Deal
Tue, Oct 14 - Sat, Oct 18
Frontier Logo
5:40 pm - 11:41 pmSAT-MDW
6h 01m1 stop
Frontier Logo
6:24 pm - 4:37 pmMDW-SAT
22h 13m1 stop
$174Frontier
Find Deal
Mon, Oct 6 - Fri, Oct 10
Southwest Logo
8:30 pm - 12:45 amSAT-MDW
4h 15m1 stop
Southwest Logo
8:15 pm - 11:05 pmMDW-SAT
2h 50mnonstop
$175Southwest
Find Deal
Fri, Oct 24 - Mon, Oct 27
Frontier Logo
8:26 pm - 11:16 amSAT-MDW
14h 50m1 stop
Frontier Logo
6:15 am - 4:50 pmMDW-SAT
10h 35m1 stop
$181Frontier
Find Deal
Thu, Oct 23 - Mon, Oct 27
Frontier Logo
11:33 am - 7:11 amSAT-MDW
19h 38m2 stops
Frontier Logo
6:20 am - 4:30 pmMDW-SAT
10h 10m1 stop
$187Frontier
Find Deal
Thu, Oct 2 - Mon, Oct 6
Frontier Logo
5:45 pm - 11:46 pmSAT-MDW
6h 01m1 stop
Frontier Logo
6:15 am - 4:50 pmMDW-SAT
10h 35m1 stop
$188Frontier
Find Deal
Fri, Oct 17 - Mon, Oct 27
Frontier Logo
5:40 pm - 11:20 pmSAT-MDW
5h 40m1 stop
Frontier Logo
6:20 am - 4:30 pmMDW-SAT
10h 10m1 stop
$189Frontier
Find Deal
Fri, Sep 26 - Mon, Sep 29
Delta Logo
6:35 am - 11:48 amSAT-MDW
5h 13m1 stop
Delta Logo
6:15 pm - 11:25 pmMDW-SAT
5h 10m1 stop
$217Delta
Find Deal
Tue, Sep 30 - Fri, Oct 3
Delta Logo
10:45 am - 4:25 pmSAT-MDW
5h 40m1 stop
Delta Logo
5:25 pm - 11:33 pmMDW-SAT
6h 08m1 stop
$317Delta
Find Deal
Wed, Jan 7 - Tue, Jan 13

Frontier flights from San Antonio to Chicago Midway Airport

Our best Frontier deals on San Antonio to Chicago Midway Airport flight tickets
Frontier
Oct 17
SAT5:45 pmSan Antonio
6h 01m
1 stop
MDW11:46 pmChicago Midway
Oct 19
MDW6:20 amChicago Midway
10h 32m
1 stop
SAT4:52 pmSan Antonio
$167
Find similar
Frontier
Oct 6
SAT5:40 pmSan Antonio
6h 01m
1 stop
MDW11:41 pmChicago Midway
Oct 10
MDW6:24 pmChicago Midway
22h 13m
1 stop
SAT4:37 pmSan Antonio
$174
Find similar
Frontier
Oct 23
SAT8:26 pmSan Antonio
14h 50m
1 stop
MDW11:16 amChicago Midway
Oct 27
MDW6:15 amChicago Midway
10h 35m
1 stop
SAT4:50 pmSan Antonio
$181
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
Oct 14
SAT7:25 pmSan Antonio
4h 40m
1 stop
MDW12:05 amChicago Midway
Oct 18
MDW6:30 amChicago Midway
4h 10m
1 stop
SAT10:40 amSan Antonio
$173
Find similar
Southwest
Oct 24
SAT8:30 pmSan Antonio
4h 15m
1 stop
MDW12:45 amChicago Midway
Oct 27
MDW8:15 pmChicago Midway
2h 50m
SAT11:05 pmSan Antonio
$175
Find similar
Southwest
Sep 30
SAT6:30 amSan Antonio
2h 35m
MDW9:05 amChicago Midway
Oct 3
MDW5:25 amChicago Midway
4h 35m
1 stop
SAT10:00 amSan Antonio
$242
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 September 15, 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-11:46 pm

1 stop6h 01m

Chicago Midway

Sun 10/19

6:20 am-4:52 pm

1 stop10h 32m

$167

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Tue 10/14

7:25 pm-12:05 am

1 stop4h 40m

Chicago Midway

Sat 10/18

6:30 am-10:40 am

1 stop4h 10m

$173

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Mon 10/6

5:40 pm-11:41 pm

1 stop6h 01m

Chicago Midway

Fri 10/10

6:24 pm-4:37 pm

1 stop22h 13m

$174

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 10/24

8:30 pm-12:45 am

1 stop4h 15m

Chicago Midway

Mon 10/27

8:15 pm-11:05 pm

Nonstop2h 50m

$175

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 10/23

8:26 pm-11:16 am

1 stop14h 50m

Chicago Midway

Mon 10/27

6:15 am-4:50 pm

1 stop10h 35m

$181

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 10/2

11:33 am-7:11 am

2 stops19h 38m

Chicago Midway

Mon 10/6

6:20 am-4:30 pm

1 stop10h 10m

$187

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 10/17

5:45 pm-11:46 pm

1 stop6h 01m

Chicago Midway

Mon 10/27

6:15 am-4:50 pm

1 stop10h 35m

$188

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 9/26

5:40 pm-11:20 pm

1 stop5h 40m

Chicago Midway

Mon 9/29

6:20 am-4:30 pm

1 stop10h 10m

$189

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Tue 9/30

6:35 am-11:48 am

1 stop5h 13m

Chicago Midway

Fri 10/3

6:15 pm-11:25 pm

1 stop5h 10m

$217

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 1/7

10:45 am-4:25 pm

1 stop5h 40m

Chicago Midway

Tue 1/13

5:25 pm-11:33 pm

1 stop6h 08m

$317

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 $305. 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 $305.

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 $393. 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 $439. 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 1% 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 September 2025, prices for San Antonio to Chicago Midway Airport flights are approximately 26% cheaper 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

$153

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 $153. The best round-trip flight deal from San Antonio to Chicago Midway Airport found on momondo in the last 72 hours is $305.
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 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 $156Free CancellationRating
5.8
3,172 reviews
Search Frontier flights
SouthwestPriceFrom $245Free CancellationRating
8.0
4,242 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 4,242 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 $426 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
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
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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