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$80+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAT
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to San Antonio are usually found in October or August, booked 63 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

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 October 22, 2025.

This Mytrip deal was found by Cheapflights users on 10/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/315:11 amORD - SAT
1 stop11h 29mFrontier
Sun 11/28:26 pmSAT - ORD
1 stop27h 49mFrontier
Deal found 10/20$156
This Frontier deal was found by Cheapflights users on 10/20. 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.
Thu 10/3012:30 pmMDW - SAT
1 stop7h 18mFrontier
Mon 11/310:04 amSAT - MDW
1 stop6h 48mFrontier
Deal found 10/20$156
This Booking.com deal was found by Cheapflights users on 10/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:20 amMDW - SAT
1 stop10h 20mFrontier
Thu 11/68:25 pmSAT - MDW
1 stop15h 05mFrontier
Deal found 10/20$158
This Mytrip deal was found by Cheapflights users on 10/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/62:26 pmORD - SAT
1 stop17h 29mFrontier
Sun 12/710:25 amSAT - ORD
1 stop13h 47mFrontier
Deal found 10/20$159
This Frontier deal was found by Cheapflights users on 10/21. 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.
Fri 11/75:11 amORD - SAT
1 stop11h 29mFrontier
Mon 11/105:35 pmSAT - ORD
1 stop6h 36mFrontier
Deal found 10/21$163
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/88:00 amORD - SAT
1 stop9h 10mMultiple Airlines
Tue 11/116:45 amSAT - ORD
2 stops18h 14mMultiple Airlines
Deal found 10/22$164
This Mytrip deal was found by Cheapflights users on 10/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1012:30 pmMDW - SAT
1 stop7h 00mFrontier
Sat 11/153:12 pmSAT - MDW
1 stop20h 18mFrontier
Deal found 10/20$164
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/56:05 pmORD - SAT
1 stop25h 01mFrontier
Mon 11/105:35 pmSAT - ORD
1 stop17h 39mFrontier
Deal found 10/21$166
This Mytrip deal was found by Cheapflights users on 10/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/25:00 amORD - SAT
1 stop13h 30mFrontier
Sun 11/210:46 pmSAT - ORD
1 stop23h 02mFrontier
Deal found 10/20$168
This Priceline deal was found by Cheapflights users on 10/20. 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.
Fri 10/246:20 amMDW - SAT
1 stop10h 30mFrontier
Sun 11/99:59 amSAT - MDW
1 stop7h 23mFrontier
Deal found 10/20$168
This Gotogate deal was found by Cheapflights users on 10/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/245:05 amORD - SAT
1 stop11h 45mFrontier
Sun 11/98:25 pmSAT - ORD
1 stop27h 50mFrontier
Deal found 10/20$169
This Trip.com deal was found by Cheapflights users on 10/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3112:30 pmMDW - SAT
1 stop7h 00mFrontier
Sun 11/28:26 pmSAT - MDW
1 stop15h 04mFrontier
Deal found 10/20$169

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 October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$156
(Priceline)

One-way from

$80
(Orbitz)

Popular in

March

Cheapest in

October

Average price

$320

Good round-trip deal

$287 or less

Good one-way deal

$158 or less
Provider with most accurate pricing for Chicago (CHI)-San Antonio flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-San Antonio flights.
Search Deals
From Chicago (CHI) to San Antonio
Search Deals
One-way flight from Chicago (CHI) to San Antonio
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to San Antonio.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to San Antonio.
Search Deals

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 October 22, 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

Tue 12/9

7:10 am-1:06 pm

1 stop5h 56m

San Antonio

Tue 12/9

5:20 pm-8:17 pm

Nonstop2h 57m

$173

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

Mon 12/8

6:13 pm-10:59 pm

1 stop4h 46m

San Antonio

Sat 12/13

5:20 pm-8:17 pm

Nonstop2h 57m

$173

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

Fri 1/9

9:04 am-12:24 pm

Nonstop3h 20m

San Antonio

Sun 1/11

2:05 pm-4:57 pm

Nonstop2h 52m

$181

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

Fri 1/9

9:04 am-12:24 pm

Nonstop3h 20m

San Antonio

Mon 1/12

7:00 am-9:51 am

Nonstop2h 51m

$181

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

Tue 12/30

6:45 am-12:28 pm

1 stop5h 43m

San Antonio

Thu 1/1

6:00 am-11:50 am

1 stop5h 50m

$199

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

Tue 12/16

9:49 am-3:47 pm

1 stop5h 58m

San Antonio

Thu 12/25

1:33 pm-7:38 pm

1 stop6h 05m

$199

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sat 12/6

6:00 am-12:11 pm

1 stop6h 11m

San Antonio

Mon 12/8

4:52 pm-11:47 pm

1 stop6h 55m

$199

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Tue 12/30

6:00 am-12:28 pm

1 stop6h 28m

San Antonio

Mon 1/5

5:20 am-12:35 pm

1 stop7h 15m

$199

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sat 12/6

11:05 am-4:43 pm

1 stop5h 38m

San Antonio

Sun 12/7

6:22 pm-11:47 pm

1 stop5h 25m

$199

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Mon 12/8

9:59 am-5:20 pm

1 stop7h 21m

San Antonio

Sat 12/13

5:55 pm-11:47 pm

1 stop5h 52m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/20

Showing 1-10 of 43 results
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Compare providers for flights from Chicago to San Antonio

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to San Antonio in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-San Antonio flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-San Antonio flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-San Antonio flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-San Antonio flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-San Antonio flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 October 17, 2025.

Booking 63 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, June is the cheapest month in which you can book a flight from Chicago to San Antonio (average of $79). Flying from Chicago to San Antonio in January is currently the most expensive (average of $186). 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 October 22, 2025.

It’s typically best to fly out from Chicago to San Antonio in the morning. Doing so could potentially save you 5% on the flight price compared to flying at noon, 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 October 19, 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. Monday at noon 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 October 22, 2025.

The most flights from CHI to SAT are scheduled on a Tuesday (28 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (10 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.

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

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 October 22, 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
4,237 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,990 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,028 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,098 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,129 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 20 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.

  • How long is the flight from Chicago to San Antonio?

    Departing from Chicago to San Antonio will take you 5h 43m. The distance between Chicago and San Antonio is about 1042 mi. This flight may include one or multiple stops.

  • 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 $172, 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 cheapest airlines to fly from Chicago to San Antonio one-way?

    One-way options have recently been found by users for as low as $90 on Southwest. Other airlines that offer cheap prices include United Airlines from $91 and Delta from $99 one-way.

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

    Consider SkyWest Airlines (100%), Republic Airways (91%) or Air Canada (86%) 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 $148. While the most popular route (Chicago O'Hare Intl - San Antonio) can be booked for $150 on average, our data indicates $449 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, June is the cheapest month in which you can book a flight from Chicago to San Antonio (average of $79). Flying from Chicago to San Antonio in January is currently the most expensive (average of $186). 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 October 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$125Average$227FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$172Average$288FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$203Average$506FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$227Average$397FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$227Average$458FlexibilityNo cancel feeOn-time69%

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