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Cheap flights from San Antonio to Chicago Midway Airport from $123

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 12/23. 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.
2:18 pm - 5:33 amSAT-MDW
15h 15m1 stop
8:41 pm - 1:16 pmMDW-SAT
16h 35m1 stop
$168Frontier
Find Deal
Thu, Dec 19 - Fri, Jan 3
5:01 pm - 7:42 pmSAT-MDW
26h 41m1 stop
6:49 pm - 4:01 pmMDW-SAT
21h 12m1 stop
$205Frontier
Find Deal
Wed, Dec 18 - Tue, Dec 24
3:31 pm - 7:32 pmSAT-MDW
28h 01m1 stop
6:49 pm - 4:24 pmMDW-SAT
21h 35m1 stop
$208Frontier
Find Deal
Thu, Dec 19 - Mon, Dec 23
7:10 pm - 10:03 amSAT-MDW
14h 53m1 stop
6:49 pm - 4:01 pmMDW-SAT
21h 12m1 stop
$218Frontier
Find Deal
Sat, Dec 7 - Tue, Dec 17
1:14 pm - 12:13 amSAT-MDW
34h 59m2 stops
8:41 pm - 1:12 pmMDW-SAT
16h 31m1 stop
Thu, Dec 12 - Thu, Dec 19
2:07 pm - 11:31 pmSAT-MDW
33h 24m3 stops
4:08 pm - 8:44 pmMDW-SAT
28h 36m2 stops
Wed, Dec 18 - Tue, Dec 24
8:10 am - 10:40 amSAT-MDW
2h 30mnonstop
5:30 pm - 11:25 pmMDW-SAT
5h 55m1 stop
$367Southwest
Find Deal
Wed, Dec 18 - Tue, Dec 24
4:55 pm - 7:30 pmSAT-MDW
2h 35mnonstop
9:50 am - 2:10 pmMDW-SAT
4h 20m1 stop
$377Southwest
Find Deal
Mon, Nov 25 - Fri, Nov 29
11:50 am - 6:32 pmSAT-MDW
6h 42m1 stop
9:30 am - 3:15 pmMDW-SAT
5h 45m1 stop
$401Delta
Find Deal
Wed, Dec 11 - Mon, Dec 16
6:30 am - 1:05 pmSAT-MDW
6h 35m1 stop
9:20 am - 5:16 pmMDW-SAT
7h 56m1 stop
$456Delta
Find Deal
Thu, May 8 - Thu, May 15
3:41 pm - 9:09 pmSAT-MDW
5h 28m1 stop
$123Frontier
Find Deal
Mon, Dec 23
1:02 pm - 12:17 amSAT-MDW
11h 15m1 stop
$129Frontier
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Mon, Jan 20
2:55 pm - 5:25 pmSAT-MDW
2h 30mnonstop
$178Southwest
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Wed, Dec 11
2:55 pm - 5:25 pmSAT-MDW
2h 30mnonstop
$179Southwest
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Tue, Dec 24
2:14 pm - 10:06 pmSAT-MDW
7h 52m1 stop
$185Delta
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Wed, Dec 11
7:10 am - 2:34 pmSAT-MDW
7h 24m1 stop
$188Delta
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Wed, Jan 1
10:25 am - 8:45 amSAT-MDW
22h 20m2 stops
$257Volaris
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Fri, Mar 7
10:25 am - 8:45 amSAT-MDW
22h 20m2 stops
$258Volaris
Find Deal
Wed, Jan 22
10:25 am - 8:30 amSAT-MDW
22h 05m2 stops
Thu, Dec 19
10:25 am - 8:45 amSAT-MDW
22h 20m2 stops
Mon, Jan 27
9:09 pm - 1:53 pmSAT-MDW
16h 44m1 stop
6:13 pm - 11:04 amMDW-SAT
16h 51m1 stop
$318Frontier
Find Deal
Sat, Nov 16 - Mon, Nov 18
12:07 pm - 3:50 pmSAT-MDW
27h 43m1 stop
12:39 pm - 8:49 pmMDW-SAT
8h 10m1 stop
$448Frontier
Find Deal
Tue, Nov 19 - Tue, Nov 26
9:09 pm - 1:53 pmSAT-MDW
16h 44m1 stop
10:59 pm - 8:17 pmMDW-SAT
21h 18m1 stop
$466Frontier
Find Deal
Sat, Nov 16 - Sun, Nov 17
6:52 pm - 1:33 amSAT-MDW
6h 41m1 stop
9:45 am - 10:29 amMDW-SAT
24h 44m1 stop
$468Frontier
Find Deal
Sun, Nov 17 - Tue, Nov 19
6:41 pm - 4:01 pmSAT-MDW
21h 20m2 stops
7:50 pm - 9:00 amMDW-SAT
13h 10m1 stop
Sun, Nov 17 - Tue, Nov 19
2:55 pm - 5:25 pmSAT-MDW
2h 30mnonstop
8:15 am - 1:10 pmMDW-SAT
4h 55m1 stop
$697Southwest
Find Deal
Tue, Nov 19 - Tue, Nov 26
9:50 am - 4:45 pmSAT-MDW
6h 55m2 stops
8:15 am - 1:10 pmMDW-SAT
4h 55m1 stop
$711Southwest
Find Deal
Tue, Nov 19 - Tue, Nov 26
10:25 am - 9:28 amSAT-MDW
23h 03m2 stops
7:50 pm - 9:00 amMDW-SAT
13h 10m1 stop
Fri, Nov 15 - Tue, Nov 19
11:50 am - 6:32 pmSAT-MDW
6h 42m1 stop
10:41 am - 4:29 pmMDW-SAT
5h 48m1 stop
$1,026Delta
Find Deal
Fri, Nov 15 - Sat, Nov 16
2:22 pm - 9:46 pmSAT-MDW
7h 24m1 stop
1:30 pm - 12:55 amMDW-SAT
11h 25m2 stops
$1,283Delta
Find Deal
Mon, Nov 18 - Mon, Nov 25
5:45 am - 8:15 amSAT-MDW
2h 30mnonstop
10:10 am - 1:10 pmMDW-SAT
3h 00mnonstop
$383Southwest
Find Deal
Sat, Dec 7 - Tue, Dec 17
8:10 am - 10:40 amSAT-MDW
2h 30mnonstop
10:55 am - 2:00 pmMDW-SAT
3h 05mnonstop
$408Southwest
Find Deal
Mon, Jan 6 - Sat, Jan 11
4:55 pm - 7:30 pmSAT-MDW
2h 35mnonstop
10:10 am - 1:10 pmMDW-SAT
3h 00mnonstop
$418Southwest
Find Deal
Fri, Dec 13 - Mon, Dec 16
6:00 am - 8:35 amSAT-MDW
2h 35mnonstop
8:15 pm - 11:05 pmMDW-SAT
2h 50mnonstop
$428Southwest
Find Deal
Sat, Apr 12 - Mon, Apr 14
4:50 pm - 7:25 pmSAT-MDW
2h 35mnonstop
10:10 am - 1:10 pmMDW-SAT
3h 00mnonstop
$471Southwest
Find Deal
Tue, Nov 26 - Wed, Dec 4
8:10 am - 10:40 amSAT-MDW
2h 30mnonstop
8:55 pm - 11:50 pmMDW-SAT
2h 55mnonstop
$472Southwest
Find Deal
Tue, Dec 3 - Sun, Dec 8
8:10 am - 10:40 amSAT-MDW
2h 30mnonstop
9:10 am - 12:10 pmMDW-SAT
3h 00mnonstop
$486Southwest
Find Deal
Fri, Dec 6 - Sun, Dec 8
8:10 am - 10:40 amSAT-MDW
2h 30mnonstop
9:15 am - 12:15 pmMDW-SAT
3h 00mnonstop
$541Southwest
Find Deal
Tue, Dec 24 - Fri, Dec 27
4:50 pm - 7:25 pmSAT-MDW
2h 35mnonstop
10:10 am - 1:10 pmMDW-SAT
3h 00mnonstop
$654Southwest
Find Deal
Wed, Nov 27 - Fri, Nov 29
5:05 pm - 7:40 pmSAT-MDW
2h 35mnonstop
4:55 pm - 7:50 pmMDW-SAT
2h 55mnonstop
$661Southwest
Find Deal
Sat, Nov 30 - Tue, Dec 3

Frontier flights from San Antonio to Chicago Midway Airport

Our best Frontier deals on San Antonio to Chicago Midway Airport flight tickets
Frontier
Dec 19
SAT2:18 pmSan Antonio
15h 15m
1 stop
MDW5:33 amChicago Midway
Jan 3
MDW8:41 pmChicago Midway
16h 35m
1 stop
SAT1:16 pmSan Antonio
Frontier
Dec 18
SAT5:01 pmSan Antonio
26h 41m
1 stop
MDW7:42 pmChicago Midway
Dec 24
MDW6:49 pmChicago Midway
21h 12m
1 stop
SAT4:01 pmSan Antonio
Frontier
Dec 19
SAT3:31 pmSan Antonio
28h 01m
1 stop
MDW7:32 pmChicago Midway
Dec 23
MDW6:49 pmChicago Midway
21h 35m
1 stop
SAT4:24 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
Dec 18
SAT8:10 amSan Antonio
2h 30m
MDW10:40 amChicago Midway
Dec 24
MDW5:30 pmChicago Midway
5h 55m
1 stop
SAT11:25 pmSan Antonio
Southwest
Nov 25
SAT4:55 pmSan Antonio
2h 35m
MDW7:30 pmChicago Midway
Nov 29
MDW9:50 amChicago Midway
4h 20m
1 stop
SAT2:10 pmSan Antonio
Southwest
Dec 7
SAT5:45 amSan Antonio
2h 30m
MDW8:15 amChicago Midway
Dec 17
MDW10:10 amChicago Midway
3h 00m
SAT1:10 pmSan Antonio

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 typical price of a round-trip flight between San Antonio and Chicago Midway Airport?

What is the cheapest month to fly from San Antonio to Chicago Midway Airport?

March. The cheapest time of year to fly to Chicago Midway Airport from San Antonio is March. Most expensive is April

What is the cheapest day to depart San Antonio for Chicago Midway Airport?

Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Monday

When is the cheapest time to fly from San Antonio to Chicago Midway Airport?

In the evening. San Antonio to Chicago Midway Airport flights are approximately 50% more expensive at noon than in the evening

What is the cheapest airline that flies to Chicago Midway Airport from San Antonio?

Frontier. Frontier, Southwest, and Delta are the most popular carriers operating from San Antonio to Chicago Midway Airport

How many flights depart from San Antonio to Chicago Midway Airport on average per day?

As of November 2024, there are 1 flights per week flying from San Antonio to Chicago Midway Airport. The most common time of day flights depart is 6:00AM, with 45% of flights taking off at noon.

How many flights depart from San Antonio to Chicago Midway Airport on average per week?

12 flights are operational weekly from San Antonio to Chicago Midway Airport as of November 2024. The most popular departure day for this route is Sunday, with 17% of flights per week taking off on this day.

Can stopping save me money on San Antonio to Chicago Midway Airport flights?

You could potentially save up to 66% 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 November 2024, prices for San Antonio to Chicago Midway Airport flights are approximately 2% 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

$123

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 $123. The best round-trip flight deal from San Antonio to Chicago Midway Airport found on momondo in the last 72 hours is $168.
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
3,551 reviews
Search Frontier flights
SouthwestPriceFrom $222Free CancellationRating
8.1
5,045 reviews
Search Southwest flights
DeltaPriceFrom $236Free CancellationRating
8.0
8,788 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 5,045 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 $403 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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