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Cheap flights from San Antonio to Chicago Midway Airport from $61

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 2/25. 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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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 from San Antonio to Chicago

The cheapest plane tickets from San Antonio to Chicago found on KAYAK recently.
3:42 pm - 5:27 pmSAT-MDW
25h 45m1 stop
6:30 pm - 2:52 pmMDW-SAT
20h 22m1 stop
$120Frontier
Find Deal
Thu, May 15 - Mon, May 19
2:18 pm - 12:17 amSAT-MDW
9h 59m1 stop
7:05 am - 1:18 pmMDW-SAT
6h 13m1 stop
$130Frontier
Find Deal
Sat, Feb 22 - Tue, Feb 25
7:10 pm - 10:02 amSAT-MDW
14h 52m1 stop
11:33 am - 6:15 pmMDW-SAT
6h 42m1 stop
$138Frontier
Find Deal
Sat, Feb 8 - Mon, Feb 10
5:40 am - 8:10 amSAT-MDW
2h 30mnonstop
6:45 pm - 9:50 pmMDW-SAT
3h 05mnonstop
$317Southwest
Find Deal
Thu, Feb 6 - Mon, Feb 10
7:45 am - 1:35 pmSAT-MDW
5h 50m1 stop
8:35 am - 11:40 amMDW-SAT
3h 05mnonstop
$327Southwest
Find Deal
Thu, Feb 6 - Mon, Feb 10
5:30 am - 11:59 amSAT-MDW
6h 29m1 stop
5:05 pm - 12:27 amMDW-SAT
7h 22m1 stop
$337Delta
Find Deal
Mon, Feb 10 - Wed, Feb 12
5:40 am - 8:10 amSAT-MDW
2h 30mnonstop
8:25 am - 11:30 amMDW-SAT
3h 05mnonstop
$342Southwest
Find Deal
Mon, Feb 10 - Wed, Feb 12
7:45 am - 1:35 pmSAT-MDW
5h 50m1 stop
8:25 am - 11:30 amMDW-SAT
3h 05mnonstop
$352Southwest
Find Deal
Mon, Feb 10 - Wed, Feb 12
5:30 am - 11:59 amSAT-MDW
6h 29m1 stop
5:05 pm - 11:21 pmMDW-SAT
6h 16m1 stop
$403Delta
Find Deal
Fri, Feb 14 - Sat, Feb 15
12:00 pm - 5:03 pmSAT-MDW
5h 03m1 stop
6:50 pm - 12:33 amMDW-SAT
5h 43m1 stop
$457Delta
Find Deal
Fri, Apr 25 - Mon, Apr 28
2:18 pm - 12:17 amSAT-MDW
9h 59m1 stop
$61Frontier
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Tue, Feb 25
9:03 am - 11:24 pmSAT-MDW
14h 21m1 stop
$64Frontier
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Tue, Apr 15
3:42 pm - 5:27 pmSAT-MDW
25h 45m1 stop
$66Frontier
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Thu, Apr 24
5:58 pm - 5:21 amSAT-MDW
11h 23m1 stop
$70Frontier
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Fri, Feb 28
6:45 am - 9:20 amSAT-MDW
2h 35mnonstop
$159Southwest
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Sat, Feb 15
5:15 am - 1:05 pmSAT-MDW
7h 50m1 stop
$169Delta
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Wed, Feb 12
11:15 am - 5:40 pmSAT-MDW
6h 25m2 stops
$174Southwest
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Sat, Feb 15
6:00 am - 10:09 amSAT-MDW
28h 09m3 stops
Thu, Mar 13
6:00 am - 10:09 amSAT-MDW
28h 09m3 stops
Thu, Mar 6
6:20 am - 12:46 pmSAT-MDW
6h 26m1 stop
$257Delta
Find Deal
Wed, Jan 29
7:10 pm - 10:02 amSAT-MDW
14h 52m1 stop
11:33 am - 6:15 pmMDW-SAT
6h 42m1 stop
$485Frontier
Find Deal
Sat, Jan 18 - Mon, Jan 20
1:02 pm - 12:17 amSAT-MDW
11h 15m1 stop
7:15 am - 12:02 pmMDW-SAT
28h 47m1 stop
$497Frontier
Find Deal
Sun, Jan 19 - Thu, Jan 23
1:02 pm - 12:17 amSAT-MDW
11h 15m1 stop
11:33 am - 6:15 pmMDW-SAT
6h 42m1 stop
$505Frontier
Find Deal
Mon, Jan 20 - Mon, Jan 27
3:35 pm - 6:10 pmSAT-MDW
2h 35mnonstop
8:25 am - 11:30 amMDW-SAT
3h 05mnonstop
$950Southwest
Find Deal
Fri, Jan 17 - Fri, Jan 24
3:35 pm - 6:10 pmSAT-MDW
2h 35mnonstop
6:25 am - 11:25 amMDW-SAT
5h 00m1 stop
$960Southwest
Find Deal
Fri, Jan 17 - Fri, Jan 24
6:30 am - 9:00 amSAT-MDW
2h 30mnonstop
1:05 pm - 7:35 pmMDW-SAT
6h 30m2 stops
$965Southwest
Find Deal
Tue, Jan 21 - Thu, Jan 23
5:15 am - 1:08 pmSAT-MDW
7h 53m1 stop
5:07 pm - 12:27 amMDW-SAT
7h 20m1 stop
$970Delta
Find Deal
Fri, Jan 17 - Fri, Jan 24
5:40 am - 8:10 amSAT-MDW
2h 30mnonstop
3:15 pm - 6:15 pmMDW-SAT
3h 00mnonstop
$1,007Southwest
Find Deal
Fri, Jan 17 - Sun, Jan 19
5:15 am - 1:08 pmSAT-MDW
7h 53m1 stop
1:26 pm - 9:57 pmMDW-SAT
8h 31m1 stop
$1,037Delta
Find Deal
Fri, Jan 17 - Mon, Jan 20
5:15 am - 1:08 pmSAT-MDW
7h 53m1 stop
2:08 pm - 12:27 amMDW-SAT
10h 19m2 stops
$1,095Delta
Find Deal
Fri, Jan 17 - Fri, Jan 24
5:40 am - 8:10 amSAT-MDW
2h 30mnonstop
5:15 pm - 8:15 pmMDW-SAT
3h 00mnonstop
$317Southwest
Find Deal
Thu, Feb 20 - Sat, Feb 22
5:40 am - 8:10 amSAT-MDW
2h 30mnonstop
8:25 am - 11:30 amMDW-SAT
3h 05mnonstop
$342Southwest
Find Deal
Mon, Feb 10 - Wed, Feb 12
6:50 am - 9:25 amSAT-MDW
2h 35mnonstop
8:35 am - 11:40 amMDW-SAT
3h 05mnonstop
$372Southwest
Find Deal
Fri, Feb 21 - Mon, Feb 24
5:05 pm - 7:40 pmSAT-MDW
2h 35mnonstop
10:10 pm - 1:10 amMDW-SAT
3h 00mnonstop
$392Southwest
Find Deal
Mon, Mar 10 - Sat, Mar 15
6:15 am - 8:45 amSAT-MDW
2h 30mnonstop
10:10 pm - 1:10 amMDW-SAT
3h 00mnonstop
$417Southwest
Find Deal
Wed, Mar 12 - Sat, Mar 15
5:05 pm - 7:40 pmSAT-MDW
2h 35mnonstop
8:15 am - 11:15 amMDW-SAT
3h 00mnonstop
$419Southwest
Find Deal
Fri, Mar 7 - Mon, Mar 10
7:00 am - 9:40 amSAT-MDW
2h 40mnonstop
9:40 pm - 12:30 amMDW-SAT
2h 50mnonstop
$427Southwest
Find Deal
Fri, Apr 25 - Sun, Apr 27
6:30 am - 9:00 amSAT-MDW
2h 30mnonstop
8:35 am - 11:40 amMDW-SAT
3h 05mnonstop
$444Southwest
Find Deal
Wed, Jan 29 - Fri, Feb 7
6:30 am - 9:00 amSAT-MDW
2h 30mnonstop
10:30 pm - 1:30 amMDW-SAT
3h 00mnonstop
$447Southwest
Find Deal
Thu, Mar 27 - Sun, Mar 30
5:05 pm - 7:40 pmSAT-MDW
2h 35mnonstop
5:15 pm - 8:15 pmMDW-SAT
3h 00mnonstop
$458Southwest
Find Deal
Thu, Mar 20 - Mon, Mar 24

Southwest flights from San Antonio to Chicago Midway Airport

Our best Southwest deals on San Antonio to Chicago Midway Airport flight tickets
Southwest
Feb 6
SAT5:40 amSan Antonio
2h 30m
MDW8:10 amChicago Midway
Feb 10
MDW6:45 pmChicago Midway
3h 05m
SAT9:50 pmSan Antonio
Southwest
Feb 6
SAT7:45 amSan Antonio
5h 50m
1 stop
MDW1:35 pmChicago Midway
Feb 10
MDW8:35 amChicago Midway
3h 05m
SAT11:40 amSan Antonio
Southwest
Feb 10
SAT5:40 amSan Antonio
2h 30m
MDW8:10 amChicago Midway
Feb 12
MDW8:25 amChicago Midway
3h 05m
SAT11:30 amSan Antonio

Frontier flights from San Antonio to Chicago Midway Airport

Our best Frontier deals on San Antonio to Chicago Midway Airport flight tickets
Frontier
May 15
SAT3:42 pmSan Antonio
25h 45m
1 stop
MDW5:27 pmChicago Midway
May 19
MDW6:30 pmChicago Midway
20h 22m
1 stop
SAT2:52 pmSan Antonio
Frontier
Feb 22
SAT2:18 pmSan Antonio
9h 59m
1 stop
MDW12:17 amChicago Midway
Feb 25
MDW7:05 amChicago Midway
6h 13m
1 stop
SAT1:18 pmSan Antonio
Frontier
Feb 8
SAT7:10 pmSan Antonio
14h 52m
1 stop
MDW10:02 amChicago Midway
Feb 10
MDW11:33 amChicago Midway
6h 42m
1 stop
SAT6:15 pmSan 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 $230. 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 $336.

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.

How have San Antonio to Chicago Midway Airport flight prices changed over time?

As of January 2025, prices for San Antonio to Chicago Midway Airport flights are approximately 95% 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

$61

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 $61. The best round-trip flight deal from San Antonio to Chicago Midway Airport found on momondo in the last 72 hours is $120.
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
6.0
3,435 reviews
Search Frontier flights
SouthwestPriceFrom $222Free CancellationRating
8.1
4,659 reviews
Search Southwest flights
DeltaPriceFrom $297Free CancellationRating
8.0
8,511 reviews
Search Delta flights
  • Southwest Flights From San Antonio to Chicago Midway Airport

    Southwest flies from San Antonio to Chicago Midway Airport around 12 times per week, with 4,659 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.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Crown Point
Schererville
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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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