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San Antonio

$79+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAT
May 21 — May 281
Thu 5/21
Thu 5/28
1 adult, Economy
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Find cheap flights from Chicago to San Antonio with Cheapflights

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Cheapflights Tip: The best prices from Chicago to San Antonio are usually found in October or August, booked 40 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap 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 April 21, 2026.

This CheapOair deal was found by Cheapflights users on 4/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/258:58 pm
ORD
-
SAT
1 stop14h 57m
Frontier
Sat 5/24:04 pm
SAT
-
ORD
1 stop17h 41m
Frontier
Deal found 4/16$291
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/119:37 pm
ORD
-
SAT
1 stop21h 22m
Frontier
Fri 5/157:54 pm
SAT
-
ORD
2 stops12h 01m
Frontier
Deal found 4/20$292
This United Airlines deal was found by Cheapflights users on 4/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/149:05 am
ORD
-
SAT
Nonstop3h 10m
United Airlines
Sat 5/166:02 pm
SAT
-
ORD
1 stop5h 13m
United Airlines
Deal found 4/20$293
This Southwest deal was found by Cheapflights users on 4/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:45 am
MDW
-
SAT
Nonstop2h 50m
Southwest
Tue 5/193:45 pm
SAT
-
MDW
1 stop6h 30m
Southwest
Deal found 4/20$293
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Mon 5/189:37 pm
ORD
-
SAT
1 stop21h 22m
Multiple Airlines
Mon 5/255:26 pm
SAT
-
ORD
1 stop29h 49m
Multiple Airlines
Deal found 4/17$295
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/99:37 pm
ORD
-
SAT
1 stop21h 22m
Frontier
Mon 5/117:54 pm
SAT
-
ORD
2 stops12h 01m
Frontier
Deal found 4/20$296
This United Airlines deal was found by Cheapflights users on 4/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/127:45 pm
ORD
-
SAT
Nonstop3h 09m
United Airlines
Tue 5/192:00 pm
SAT
-
ORD
Nonstop2h 55m
United Airlines
Deal found 4/17$297
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/129:00 pm
MDW
-
SAT
Nonstop2h 50m
Southwest
Wed 5/132:35 pm
SAT
-
MDW
Nonstop2h 35m
Southwest
Deal found 4/16$297
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Fri 5/159:37 pm
ORD
-
SAT
1 stop21h 22m
Frontier
Wed 5/207:54 pm
SAT
-
ORD
2 stops11h 57m
Frontier
Deal found 4/16$298
This Gotogate deal was found by Cheapflights users on 4/20. 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 5/85:05 am
ORD
-
SAT
1 stop11h 11m
Multiple Airlines
Mon 5/187:54 pm
SAT
-
ORD
1 stop24h 38m
Multiple Airlines
Deal found 4/20$299
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Thu 5/149:37 pm
ORD
-
SAT
1 stop21h 22m
Frontier
Tue 5/267:54 pm
SAT
-
ORD
2 stops12h 01m
Frontier
Deal found 4/17$300
This Southwest deal was found by Cheapflights users on 4/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/269:00 pm
MDW
-
SAT
Nonstop2h 50m
Southwest
Fri 5/292:40 pm
SAT
-
MDW
Nonstop2h 35m
Southwest
Deal found 4/19$300

Find 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 April 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$291
(Kiwi.com)

One-way from

$79
(eDestinos)

Popular in

April

Cheapest in

October

Average price

$431

Good round-trip deal

$332 or less

Good one-way deal

$223 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. 5% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
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 April 21, 2026.
Use the filters below to find and compare flights from Chicago to San Antonio that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

Wed 5/13

7:45 pm-10:54 pm

Nonstop3h 09m

San Antonio

Mon 5/18

5:49 pm-8:45 pm

Nonstop2h 56m

$303

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

Thu 5/28

6:00 am-12:43 pm

1 stop6h 43m

San Antonio

Wed 6/10

5:18 pm-8:21 pm

Nonstop3h 03m

$313

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Tue 6/9

6:05 am-1:21 pm

1 stop7h 16m

San Antonio

Wed 6/17

2:29 pm-10:17 pm

1 stop7h 48m

$317

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Thu 5/7

9:40 pm-12:30 am

Nonstop2h 50m

San Antonio

Mon 5/11

3:20 pm-9:05 pm

1 stop5h 45m

$319

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Thu 5/28

5:30 am-11:25 am

2 stops5h 55m

San Antonio

Wed 6/10

11:25 am-5:00 pm

2 stops5h 35m

$333

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

Fri 5/8

7:45 pm-10:54 pm

Nonstop3h 09m

San Antonio

Mon 5/11

5:49 pm-8:45 pm

Nonstop2h 56m

$343

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Mon 6/1

6:15 pm-12:15 am

1 stop6h 00m

San Antonio

Sat 6/6

5:10 am-1:10 pm

2 stops8h 00m

$350

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sat 5/30

3:30 pm-11:10 pm

2 stops7h 40m

San Antonio

Fri 6/5

5:25 pm-9:55 pm

1 stop4h 30m

$351

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

Sat 5/16

5:30 am-1:16 pm

1 stop7h 46m

San Antonio

Tue 5/19

5:34 pm-8:36 pm

Nonstop3h 02m

$357

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Thu 5/14

6:00 am-11:40 am

1 stop5h 40m

San Antonio

Thu 5/21

12:20 pm-5:05 pm

1 stop4h 45m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/19

Showing 1-10 of 43 resultsSorted by cheapest first
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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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Super.comPrice 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 April 17, 2026.

Booking 40 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, January is the cheapest month in which you can book a flight from Chicago to San Antonio (average of $88). Flying from Chicago to San Antonio in April is currently the most expensive (average of $188). 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 April 21, 2026.

It’s typically best to fly out from Chicago to San Antonio in the afternoon. Doing so could potentially save you 9% 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 April 18, 2026.

Travelers seeking maximum savings on their Chicago to San Antonio flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday 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 April 21, 2026.

The most flights from CHI to SAT are scheduled on a Friday (29 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (20 on average).

How much does it cost to fly round-trip from Chicago to San Antonio?

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 60% 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.

Los Angeles (LAX) is the most affordable 1-stop option, with an average round-trip price of $236.

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

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to San Antonio trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD, MDW and SAT

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 April 21, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican 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
4,331 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

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
4,331 reviews
Southwest
8.0
Very good
4,331 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

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
9,612 reviews
Southwest
8.0
Very good
4,331 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

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
7.1
Good
11,646 reviews
Southwest
8.0
Very good
4,331 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

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
5.7
Fair
2,981 reviews
Southwest
8.0
Very good
4,331 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

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 23 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 2h 50m. The distance between Chicago and San Antonio is about 1036 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 $101. Other airlines that can offer you cheap pricing are Spirit Airlines, from $176, and United Airlines, from $213. Frontier is priced at 73% 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 $55 on Frontier. Other airlines that offer cheap prices include Southwest from $76 and Spirit Airlines from $111 one-way.

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

    Consider Japan Airlines (75%), Envoy Air (75%) or British Airways (75%) 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 $188. While the most popular route (Chicago O'Hare Intl - San Antonio) can be booked for $227 on average, our data indicates $453 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, January is the cheapest month in which you can book a flight from Chicago to San Antonio (average of $88). Flying from Chicago to San Antonio in April is currently the most expensive (average of $188). 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 April 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$101Average$214FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$176Average$259FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$213Average$406FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$232Average$421FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$256Average$440FlexibilityNo cancel feeOn-time63%

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