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Cheap flights from San Antonio to Chicago from $53

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 8/25. 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

Frontier Logo
5:35 pm - 11:20 pmSAT-MDW
5h 45m1 stop
Frontier Logo
6:20 am - 4:30 pmMDW-SAT
10h 10m1 stop
$146Frontier
Find Deal
vie., sep. 5 - lun., sep. 8
Frontier Logo
5:35 pm - 11:20 pmSAT-MDW
5h 45m1 stop
Frontier Logo
6:20 am - 4:30 pmMDW-SAT
10h 10m1 stop
$149Frontier
Find Deal
vie., sep. 12 - lun., sep. 15
Frontier Logo
5:35 pm - 11:20 pmSAT-MDW
5h 45m1 stop
Frontier Logo
6:20 am - 4:30 pmMDW-SAT
10h 10m1 stop
$168Frontier
Find Deal
vie., sep. 19 - lun., sep. 22
Southwest Logo
3:20 pm - 6:00 pmSAT-MDW
2h 40mnonstop
Southwest Logo
8:15 pm - 11:05 pmMDW-SAT
2h 50mnonstop
$235Southwest
Find Deal
jue., oct. 2 - lun., oct. 6
Southwest Logo
5:35 pm - 8:15 pmSAT-MDW
2h 40mnonstop
Southwest Logo
7:05 am - 2:10 pmMDW-SAT
7h 05m1 stop
$245Southwest
Find Deal
mar., jul. 29 - mar., ago. 5
Southwest Logo
8:30 am - 4:35 pmSAT-MDW
8h 05m2 stops
Southwest Logo
7:40 am - 10:20 amMDW-SAT
2h 40mnonstop
$250Southwest
Find Deal
sáb., ago. 9 - lun., ago. 11
Delta Logo
5:20 am - 12:29 pmSAT-MDW
7h 09m1 stop
Delta Logo
1:46 pm - 9:25 pmMDW-SAT
7h 39m1 stop
$255Delta
Find Deal
mar., jul. 29 - mar., ago. 5
Southwest Logo
3:20 pm - 6:00 pmSAT-MDW
2h 40mnonstop
Southwest Logo
8:15 pm - 11:05 pmMDW-SAT
2h 50mnonstop
$256Southwest
Find Deal
jue., oct. 9 - lun., oct. 13
Delta Logo
11:25 am - 6:40 pmSAT-MDW
7h 15m1 stop
Delta Logo
9:25 am - 3:31 pmMDW-SAT
6h 06m1 stop
$280Delta
Find Deal
mié., jul. 30 - vie., ago. 1
Delta Logo
3:25 pm - 9:36 pmSAT-MDW
6h 11m1 stop
Delta Logo
6:15 pm - 11:25 pmMDW-SAT
5h 10m1 stop
$305Delta
Find Deal
vie., sep. 19 - dom., sep. 28

Frontier flights from San Antonio to Chicago Midway Airport

Our best Frontier deals on San Antonio to Chicago Midway Airport flight tickets
Frontier
Sep 5
SAT5:35 pmSan Antonio
5h 45m
1 stop
MDW11:20 pmChicago Midway
Sep 8
MDW6:20 amChicago Midway
10h 10m
1 stop
SAT4:30 pmSan Antonio
Frontier
Sep 12
SAT5:35 pmSan Antonio
5h 45m
1 stop
MDW11:20 pmChicago Midway
Sep 15
MDW6:20 amChicago Midway
10h 10m
1 stop
SAT4:30 pmSan Antonio
Frontier
Sep 19
SAT5:35 pmSan Antonio
5h 45m
1 stop
MDW11:20 pmChicago Midway
Sep 22
MDW6:20 amChicago Midway
10h 10m
1 stop
SAT4:30 pmSan Antonio

Southwest flights from San Antonio to Chicago Midway Airport

Our best Southwest deals on San Antonio to Chicago Midway Airport flight tickets
Southwest
Oct 2
SAT3:20 pmSan Antonio
2h 40m
MDW6:00 pmChicago Midway
Oct 6
MDW8:15 pmChicago Midway
2h 50m
SAT11:05 pmSan Antonio
Southwest
Jul 29
SAT5:35 pmSan Antonio
2h 40m
MDW8:15 pmChicago Midway
Aug 5
MDW7:05 amChicago Midway
7h 05m
1 stop
SAT2:10 pmSan Antonio
Southwest
Aug 9
SAT8:30 amSan Antonio
8h 05m
2 stops
MDW4:35 pmChicago Midway
Aug 11
MDW7:40 amChicago Midway
2h 40m
SAT10:20 amSan Antonio

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 $347. 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, 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 $406. 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 $434. 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 24% 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 June 2025, prices for San Antonio to Chicago Midway Airport flights are approximately 44% 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

$53

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 $53. The best round-trip flight deal from San Antonio to Chicago Midway Airport found on momondo in the last 72 hours is $146.
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.

  • 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
5.9
3,290 reviews
Search Frontier flights
SouthwestPriceFrom $235Free CancellationRating
8.0
4,278 reviews
Search Southwest flights
DeltaPriceFrom $241Free CancellationRating
8.0
7,973 reviews
Search Delta flights
  • Southwest Flights From San Antonio to Chicago Midway Airport

    Southwest flies from San Antonio to Chicago Midway Airport around 14 times per week, with 4,278 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 $235 (round-trip), much lower than the average airfare cost of $427 for Southwest flights on this route.


Traveling to a place near Chicago?

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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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