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Cheap flights from San Antonio to Chicago Midway Airport from $60

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 Midway Airport departing on 1/30. 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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Find the cheapest flights from San Antonio to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from San Antonio to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from San Antonio to Chicago.

Cheap last minute flights

Planning a quick getaway from San Antonio to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from San Antonio to Chicago

Find recent round-trip train or bus tickets from San Antonio to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
1:02 pm - 12:13 amSAT-MDW
11h 11m1 stop
8:15 am - 12:02 pmMDW-SAT
27h 47m1 stop
$118Frontier
Find Deal
Mon, Jan 13 - Wed, Jan 15
8:20 pm - 11:48 amSAT-MDW
15h 28m1 stop
7:15 am - 11:56 amMDW-SAT
28h 41m1 stop
$119Frontier
Find Deal
Thu, Jan 9 - Sun, Jan 12
7:10 pm - 10:02 amSAT-MDW
14h 52m1 stop
3:37 pm - 6:15 pmMDW-SAT
26h 38m1 stop
$127Frontier
Find Deal
Sat, Jan 18 - Fri, Jan 24
1:02 pm - 12:17 amSAT-MDW
11h 15m1 stop
11:33 am - 6:15 pmMDW-SAT
6h 42m1 stop
$128Frontier
Find Deal
Thu, Jan 23 - Mon, Jan 27
6:30 am - 9:00 amSAT-MDW
2h 30mnonstop
7:05 pm - 10:10 pmMDW-SAT
3h 05mnonstop
$350Southwest
Find Deal
Tue, Feb 11 - Thu, Feb 13
6:30 am - 9:00 amSAT-MDW
2h 30mnonstop
5:20 am - 10:00 amMDW-SAT
4h 40m1 stop
$359Southwest
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Wed, Feb 12 - Tue, Feb 18
5:30 am - 11:59 amSAT-MDW
6h 29m1 stop
3:41 pm - 9:54 pmMDW-SAT
6h 13m1 stop
$377Delta
Find Deal
Thu, Jan 23 - Sat, Jan 25
6:20 am - 12:46 pmSAT-MDW
6h 26m1 stop
5:07 pm - 12:27 amMDW-SAT
7h 20m1 stop
$382Delta
Find Deal
Thu, Jan 23 - Tue, Jan 28
10:09 am - 5:54 pmSAT-MDW
7h 45m1 stop
1:24 pm - 1:12 pmMDW-SAT
23h 48m2 stops
Sat, Dec 28 - Mon, Dec 30
10:09 am - 5:54 pmSAT-MDW
7h 45m1 stop
1:24 pm - 11:26 pmMDW-SAT
34h 02m3 stops
Sat, Dec 28 - Mon, Dec 30
1:02 pm - 12:17 amSAT-MDW
11h 15m1 stop
$60Frontier
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Thu, Jan 30
8:20 pm - 11:48 amSAT-MDW
15h 28m1 stop
$61Frontier
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Thu, Jan 9
7:10 pm - 10:02 amSAT-MDW
14h 52m1 stop
$62Frontier
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Sat, Jan 25
2:18 pm - 12:17 amSAT-MDW
9h 59m1 stop
$64Frontier
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Tue, Feb 18
5:40 am - 8:10 amSAT-MDW
2h 30mnonstop
$175Southwest
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Fri, Jan 17
8:10 am - 10:40 amSAT-MDW
2h 30mnonstop
$184Southwest
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Wed, Jan 1
4:25 pm - 10:27 pmSAT-MDW
6h 02m1 stop
$223Delta
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Thu, Mar 20
5:20 am - 12:33 pmSAT-MDW
7h 13m1 stop
$256Delta
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Mon, Apr 7
2:07 pm - 11:20 pmSAT-MDW
33h 13m2 stops
Fri, Dec 27
2:07 pm - 12:27 amSAT-MDW
34h 20m3 stops
Fri, Dec 27
3:41 pm - 9:09 pmSAT-MDW
5h 28m1 stop
12:58 pm - 4:57 pmMDW-SAT
27h 59m1 stop
$478Frontier
Find Deal
Mon, Dec 23 - Thu, Jan 2
3:31 pm - 7:32 pmSAT-MDW
28h 01m1 stop
6:49 pm - 9:09 amMDW-SAT
14h 20m1 stop
$545Frontier
Find Deal
Thu, Dec 19 - Fri, Jan 3
2:18 pm - 5:33 amSAT-MDW
15h 15m1 stop
6:49 pm - 9:09 amMDW-SAT
14h 20m1 stop
$565Frontier
Find Deal
Thu, Dec 19 - Fri, Jan 3
2:50 pm - 8:35 pmSAT-MDW
5h 45m2 stops
7:00 pm - 1:15 amMDW-SAT
6h 15m1 stop
$721Southwest
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Mon, Dec 23 - Mon, Dec 30
4:35 pm - 10:06 pmSAT-MDW
5h 31m1 stop
4:50 pm - 11:56 pmMDW-SAT
7h 06m1 stop
$746Delta
Find Deal
Sat, Dec 21 - Tue, Dec 24
5:05 pm - 7:40 pmSAT-MDW
2h 35mnonstop
8:05 am - 11:05 amMDW-SAT
3h 00mnonstop
$751Southwest
Find Deal
Sat, Dec 21 - Sat, Jan 4
5:20 pm - 11:30 pmSAT-MDW
6h 10m1 stop
8:05 am - 11:05 amMDW-SAT
3h 00mnonstop
$760Southwest
Find Deal
Sat, Dec 21 - Sat, Jan 4
5:05 pm - 7:40 pmSAT-MDW
2h 35mnonstop
9:50 am - 2:10 pmMDW-SAT
4h 20m1 stop
$777Southwest
Find Deal
Sat, Dec 21 - Tue, Dec 24
7:10 am - 4:24 pmSAT-MDW
9h 14m2 stops
5:04 pm - 11:56 pmMDW-SAT
6h 52m1 stop
$1,057Delta
Find Deal
Mon, Dec 23 - Thu, Jan 2
4:35 pm - 10:06 pmSAT-MDW
5h 31m1 stop
9:30 am - 6:08 pmMDW-SAT
8h 38m2 stops
$1,101Delta
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Sat, Dec 21 - Sat, Jan 4
6:30 am - 9:00 amSAT-MDW
2h 30mnonstop
7:05 pm - 10:10 pmMDW-SAT
3h 05mnonstop
$350Southwest
Find Deal
Tue, Feb 11 - Thu, Feb 13
6:30 am - 9:00 amSAT-MDW
2h 30mnonstop
3:15 pm - 6:15 pmMDW-SAT
3h 00mnonstop
$364Southwest
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Fri, Jan 10 - Tue, Jan 14
6:30 am - 9:00 amSAT-MDW
2h 30mnonstop
10:55 am - 2:00 pmMDW-SAT
3h 05mnonstop
$384Southwest
Find Deal
Tue, Jan 7 - Sat, Jan 11
6:30 am - 9:00 amSAT-MDW
2h 30mnonstop
8:35 am - 11:40 amMDW-SAT
3h 05mnonstop
$389Southwest
Find Deal
Wed, Feb 5 - Fri, Feb 7
2:25 pm - 5:00 pmSAT-MDW
2h 35mnonstop
8:25 am - 11:30 amMDW-SAT
3h 05mnonstop
$398Southwest
Find Deal
Mon, Feb 3 - Wed, Feb 12
6:00 am - 8:35 amSAT-MDW
2h 35mnonstop
9:10 am - 12:00 pmMDW-SAT
2h 50mnonstop
$428Southwest
Find Deal
Sat, May 24 - Sun, May 25
6:50 am - 9:25 amSAT-MDW
2h 35mnonstop
8:25 am - 11:30 amMDW-SAT
3h 05mnonstop
$431Southwest
Find Deal
Fri, Jan 3 - Tue, Jan 7
6:30 am - 9:00 amSAT-MDW
2h 30mnonstop
8:25 am - 11:30 amMDW-SAT
3h 05mnonstop
$436Southwest
Find Deal
Sun, Jan 5 - Wed, Jan 8
6:00 am - 8:30 amSAT-MDW
2h 30mnonstop
10:10 pm - 1:10 amMDW-SAT
3h 00mnonstop
$468Southwest
Find Deal
Sat, Mar 15 - Sat, Mar 22
6:30 am - 9:00 amSAT-MDW
2h 30mnonstop
7:50 pm - 10:45 pmMDW-SAT
2h 55mnonstop
$494Southwest
Find Deal
Thu, Jan 2 - Thu, Jan 2

Frontier flights from San Antonio to Chicago Midway Airport

Our best Frontier deals on San Antonio to Chicago Midway Airport flight tickets
Frontier
Jan 13
SAT1:02 pmSan Antonio
11h 11m
1 stop
MDW12:13 amChicago Midway
Jan 15
MDW8:15 amChicago Midway
27h 47m
1 stop
SAT12:02 pmSan Antonio
Frontier
Jan 9
SAT8:20 pmSan Antonio
15h 28m
1 stop
MDW11:48 amChicago Midway
Jan 12
MDW7:15 amChicago Midway
28h 41m
1 stop
SAT11:56 amSan Antonio
Frontier
Jan 18
SAT7:10 pmSan Antonio
14h 52m
1 stop
MDW10:02 amChicago Midway
Jan 24
MDW3:37 pmChicago Midway
26h 38m
1 stop
SAT6:15 pmSan Antonio

Delta flights from San Antonio to Chicago Midway Airport

Our best Delta deals on San Antonio to Chicago Midway Airport flight tickets
Delta
Jan 23
SAT5:30 amSan Antonio
6h 29m
1 stop
MDW11:59 amChicago Midway
Jan 25
MDW3:41 pmChicago Midway
6h 13m
1 stop
SAT9:54 pmSan Antonio
Delta
Jan 23
SAT6:20 amSan Antonio
6h 26m
1 stop
MDW12:46 pmChicago Midway
Jan 28
MDW5:07 pmChicago Midway
7h 20m
1 stop
SAT12:27 amSan Antonio
Delta
Jan 8
SAT5:25 amSan Antonio
7h 43m
1 stop
MDW1:08 pmChicago Midway
Jan 15
MDW5:07 pmChicago Midway
7h 20m
1 stop
SAT12:27 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 March is, on average, the cheapest month to fly to Chicago Midway Airport from San Antonio, with most prices found around $302. If you are unable to visit Chicago Midway Airport during the month of March, then departing from San Antonio during the month June is also very affordable. Most momondo users find prices during this month for around $317.

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 $340. 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 $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 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 $425. 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 65% 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 December 2024, prices for San Antonio to Chicago Midway Airport flights are approximately 258% 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

$60

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 $60. The best round-trip flight deal from San Antonio to Chicago Midway Airport found on momondo in the last 72 hours is $118.
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.

  • 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 $147Free CancellationRating
6.1
3,479 reviews
Search Frontier flights
SouthwestPriceFrom $222Free CancellationRating
8.1
4,848 reviews
Search Southwest flights
DeltaPriceFrom $236Free CancellationRating
8.0
8,604 reviews
Search Delta flights
  • Southwest Flights From San Antonio to Chicago Midway Airport

    Southwest flies from San Antonio to Chicago Midway Airport around 6 times per week, with 4,848 momondo users rating the airline 8.1/10. The cheapest Southwest deal from San Antonio to Chicago Midway Airport in the last 72 hours was $222 (round-trip), much lower than the average airfare cost of $428 for Southwest flights on this route.


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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