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$73+ Cheap flights from Chicago (CHI) to San Antonio (SAT)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAT
août 19 — août 261
mar. 8/19
mar. 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to San Antonio are usually found in August or September, booked 71 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap flight deals from Chicago to San Antonio

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to San Antonio (SAT). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated août 14, 2025.

Round-trip from

$227
(Cheapflightsfares)

One-way from

$73
(Priceline)

Popular in

March

Cheapest in

August

Average price

$337

Good round-trip deal

$235 or less

Good one-way deal

$142 or less
From Chicago (CHI) to San Antonio
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One-way flight from Chicago (CHI) to San Antonio
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Highest demand for flights based on searches. 7% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago (CHI) to San Antonio.
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Price to beat on a one-way flight from Chicago (CHI) to San Antonio.
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Find flight deals from Chicago to San Antonio

Cheapest flights from Chicago to San Antonio
Explore the most affordable flight options available from Chicago to San Antonio. Find the lowest fares from popular airlines and budget airlines, with prices last updated on août 14, 2025.

This FlightHub deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 9/36:55 pmORD - SAT
1 stop15h 53mMultiple Airlines
jeu. 9/42:54 pmSAT - ORD
1 stop7h 04mMultiple Airlines
Deal found 8/13$227
This Frontier deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 9/266:20 amMDW - SAT
1 stop10h 10mFrontier
dim. 9/288:20 pmSAT - MDW
2 stops16h 24mFrontier
Deal found 8/14$227
This Frontier deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 8/2111:44 amORD - SAT
1 stop7h 49mFrontier
jeu. 9/411:33 amSAT - ORD
1 stop12h 37mFrontier
Deal found 8/12$229
This FlightHub deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 9/1210:42 amORD - SAT
1 stop8h 33mMultiple Airlines
mar. 9/169:47 pmSAT - ORD
1 stop21h 04mMultiple Airlines
Deal found 8/14$230
This FlightHub deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 9/145:05 amORD - SAT
1 stop13h 07mSpirit Airlines
mer. 9/179:47 pmSAT - ORD
1 stop14h 04mSpirit Airlines
Deal found 8/13$231
This Cheapflightsfares deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 8/286:00 amORD - SAT
1 stop7h 53mSpirit Airlines
jeu. 9/42:54 pmSAT - ORD
1 stop7h 04mSpirit Airlines
Deal found 8/13$232
This American Airlines deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/216:45 amORD - SAT
1 stop9h 02mAmerican Airlines
mar. 10/286:03 amSAT - ORD
Nonstop2h 55mAmerican Airlines
Deal found 8/14$233
This Frontier deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 8/167:00 amORD - SAT
1 stop11h 02mFrontier
jeu. 9/411:33 amSAT - ORD
1 stop12h 37mFrontier
Deal found 8/12$234
This Justfly.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 9/138:25 amORD - SAT
1 stop6h 02mMultiple Airlines
dim. 9/148:37 pmSAT - ORD
1 stop15h 22mMultiple Airlines
Deal found 8/12$235
This Cheapflightsfares deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/239:00 amORD - SAT
1 stop11h 52mSpirit Airlines
ven. 9/2612:45 pmSAT - ORD
1 stop9h 13mSpirit Airlines
Deal found 8/12$236
This Priceline deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 8/167:00 amORD - SAT
1 stop11h 02mFrontier
lun. 8/185:38 pmSAT - ORD
1 stop6h 44mFrontier
Deal found 8/12$237
This Orbitz deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 9/115:10 amORD - SAT
1 stop5h 38mFrontier
jeu. 9/1811:33 amSAT - ORD
1 stop12h 37mFrontier
Deal found 8/12$238

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to San Antonio 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, Cheapflights users made 2,558,603 searches. Data last updated août 14, 2025.
Use the filters below to find and compare flights from Chicago to San Antonio that are best for you.

Fly from

Chicago

Fly to

San Antonio

Route

Depart

Return

Price

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

jeu. 11/6

10:18 am-10:27 pm

1 stop12h 09m

San Antonio

mer. 11/12

6:00 am-5:04 pm

1 stop11h 04m

$227

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

sam. 9/27

8:25 am-4:42 pm

1 stop8h 17m

San Antonio

sam. 10/4

1:44 pm-9:45 pm

1 stop8h 01m

$227

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

mer. 9/3

6:55 pm-10:48 am

1 stop15h 53m

San Antonio

jeu. 9/4

2:54 pm-9:58 pm

1 stop7h 04m

$227

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

ven. 9/26

6:20 am-4:30 pm

1 stop10h 10m

San Antonio

dim. 9/28

8:20 pm-12:44 pm

2 stops16h 24m

$227

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

jeu. 9/4

10:42 am-7:15 pm

1 stop8h 33m

San Antonio

jeu. 9/11

11:33 am-12:10 am

1 stop12h 37m

$229

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

jeu. 11/6

6:05 am-10:27 pm

1 stop16h 22m

San Antonio

dim. 11/9

6:00 am-9:23 pm

1 stop15h 23m

$229

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

jeu. 8/21

11:44 am-7:33 pm

1 stop7h 49m

San Antonio

jeu. 9/4

11:33 am-12:10 am

1 stop12h 37m

$229

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

jeu. 8/21

11:44 am-7:33 pm

1 stop7h 49m

San Antonio

lun. 8/25

5:27 pm-11:54 pm

1 stop6h 27m

$229

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

ven. 9/12

10:42 am-7:15 pm

1 stop8h 33m

San Antonio

mar. 9/16

9:47 pm-6:51 pm

1 stop21h 04m

$230

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

mer. 10/22

7:15 am-3:14 pm

1 stop7h 59m

San Antonio

ven. 10/24

5:00 pm-9:58 pm

1 stop28h 58m

$230

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 46 results
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The best insider tips for Chicago to San Antonio flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to San Antonio trip
Airports
ORD

Expect long walks between terminals at ORD; plan extra time for navigating this busy airport.

Read more about ORDby Ramsey Qubein
MDW

Use the 'L' train for a quick, cost-effective way to reach MDW from downtown Chicago in under 30 minutes.

Read more about MDWby Ramsey Qubein
SAT

For a quick ride to downtown San Antonio, use rideshare services from SAT, taking about 15 minutes.

Read more about SATby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD, MDW and SAT

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Best time to book a flight from Chicago to San Antonio

Have a flexible travel schedule? Discover the best time to fly to San Antonio from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to San Antonio

How far ahead should I book a flight from Chicago to San Antonio?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to San Antonio. Price data was last updated on August 8, 2025.

Booking 71 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to San Antonio. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to San Antonio?

Currently, August is the cheapest month in which you can book a flight from Chicago to San Antonio (average of $295). Flying from Chicago to San Antonio in March is currently the most expensive (average of $376). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to SAT?

Find hourly flight availability from Chicago to San Antonio. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated août 14, 2025.

It’s typically best to fly out from Chicago to San Antonio at noon. Doing so could potentially save you 12% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Chicago to San Antonio?

Use this chart to determine the cheapest time to fly round-trip from Chicago to San Antonio. Price data was last updated on August 10, 2025.

Travelers seeking maximum savings on their Chicago to San Antonio flight should consider departing on Tuesday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to San Antonio

Explore weekly flight availability from Chicago to San Antonio. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated août 14, 2025.

The most flights from CHI to SAT are scheduled on a Thursday (33 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).

What’s the top layover airport for flights from Chicago to San Antonio?

Share of 1-stop round-trip flights from Chicago to San Antonio chosen by Cheapflights users in the past 12 months, using the same layover each way.

Orlando (MCO) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago to San Antonio on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to San Antonio?

Average round-trip fare for 1-stop flights from Chicago to San Antonio, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Fort Lauderdale (FLL) is the most affordable 1-stop option, with an average round-trip price of $227.

What’s the fastest layover option from Chicago to San Antonio?

Shortest average travel time for 1-stop one-way flights from Chicago to San Antonio, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Orlando (MCO) have the shortest average one-way travel time for 1-stop routes: 9h 22m.

Which airport typically offers the quickest layover for flights from Chicago to San Antonio?

Average layover duration for 1-stop one-way flights from Chicago to San Antonio, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Orlando (MCO) offer the fastest connection on this route, with an average layover time of 2h 47m.

Reviews of airlines servicing San Antonio

Get insights into the airlines that provide service to San Antonio. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Antonio. Reviews last updated août 14, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and American Airlines from Chicago to San Antonio. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Spirit Airlines
6.3
Okay
8,045 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
5.8
Fair
3,219 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Chicago to San Antonio. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to San Antonio from Chicago?

    San Antonio (SAT) is the airport you will fly into if you book a flight from Chicago to San Antonio. You should not have trouble finding flights to San Antonio from Chicago; the airport handles an average of 21 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 5 airlines have flights to the San Antonio airport from Chicago. It is only a 7.6 mi journey from San Antonio (SAT) to San Antonio’s city center.

  • What are the cheapest airlines flying from Chicago to San Antonio round-trip?

    Cheapflights users have booked flights from Chicago to San Antonio round-trip from $125. Other airlines that can offer you cheap pricing are Spirit Airlines, from $167, and Southwest, from $203. Frontier is priced at 68% lower than the current average price of a flight leaving 3 months from now.

  • What are the most reliable airlines from Chicago to San Antonio?

    Consider SkyWest Airlines (82%), Air Canada (72%) or United Airlines (72%) when booking your flight. These represent the most reliable airlines when flying from Chicago to San Antonio.

  • What are the cheapest flights from Chicago to San Antonio?

    Looking at all options, your cheapest flight can be booked for $86. While the most popular route (Chicago O'Hare Intl - San Antonio) can be booked for $184 on average our data indicates $405 when flying from Chicago to San Antonio.

  • Can I find deals for flights from Chicago to San Antonio that include hotel bookings?

    Yes. In addition to deals on Chicago to San Antonio flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to San Antonio?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to San Antonio.

  • Can I find deals for business class flights from Chicago to San Antonio?

    Yes. Cheapflights offers flight deals from Chicago to San Antonio by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to San Antonio?

    Currently, August is the cheapest month in which you can book a flight from Chicago to San Antonio (average of $295). Flying from Chicago to San Antonio in March is currently the most expensive (average of $376). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near San Antonio?

Book flights to San Antonio if you plan to visit one of these locations
New Braunfels
Kerrville

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Alternative routes for Chicago to San Antonio

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chicago to San Antonio

Discover the top 5 airlines that operate flights from Chicago to San Antonio. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated août 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$125Average$218FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$167Average$266FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$203Average$499FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$207Average$402FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$277Average$473FlexibilityNo cancel feeOn-time69%

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