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$63+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAT
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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Find cheap flights from Chicago to San Antonio with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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Cheapflights Tip: The best prices from Chicago to San Antonio are usually found in October or August, booked 50 days in advance, depart on a Tuesday or Wednesday 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 December 4, 2025.

This Priceline deal was found by Cheapflights users on 12/3. 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.
Wed 12/316:05 amORD - SAT
1 stop10h 56mMultiple Airlines
Wed 1/712:45 pmSAT - ORD
1 stop6h 17mMultiple Airlines
Deal found 12/3$176
This CheapOair deal was found by Cheapflights users on 12/3. 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 12/132:26 pmORD - SAT
1 stop17h 29mFrontier
Sun 12/216:45 amSAT - ORD
1 stop17h 27mFrontier
Deal found 12/3$195
This CheapOair deal was found by Cheapflights users on 12/1. 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.
Fri 12/196:00 amORD - SAT
1 stop11h 01mFrontier
Sun 12/216:45 amSAT - ORD
1 stop17h 27mFrontier
Deal found 12/1$199
This CheapOair deal was found by Cheapflights users on 12/1. 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.
Fri 12/198:15 amMDW - SAT
1 stop8h 46mFrontier
Sun 12/2110:18 amSAT - MDW
1 stop13h 03mFrontier
Deal found 12/1$199
This Mytrip deal was found by Cheapflights users on 12/2. 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.
Thu 12/187:00 amORD - SAT
1 stop6h 14mFrontier
Sun 12/216:45 amSAT - ORD
1 stop17h 27mFrontier
Deal found 12/2$205
This Travelocity deal was found by Cheapflights users on 12/3. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 amORD - SAT
1 stop10h 56mMultiple Airlines
Tue 1/612:45 pmSAT - ORD
1 stop6h 17mMultiple Airlines
Deal found 12/3$211
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/316:12 amMDW - SAT
1 stop10h 49mFrontier
Tue 1/63:55 pmSAT - MDW
2 stops30h 22mFrontier
Deal found 12/3$212
This Southwest deal was found by Cheapflights users on 12/2. 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.
Wed 12/178:25 amMDW - SAT
Nonstop3h 00mSouthwest
Wed 1/282:10 pmSAT - MDW
Nonstop2h 35mSouthwest
Deal found 12/2$216
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/246:05 amORD - SAT
1 stop10h 56mFrontier
Thu 12/2510:18 amSAT - ORD
1 stop10h 05mFrontier
Deal found 12/2$220
This CheapOair deal was found by Cheapflights users on 12/3. 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.
Thu 12/183:10 pmMDW - SAT
1 stop27h 32mFrontier
Sun 12/216:45 amSAT - MDW
1 stop15h 05mFrontier
Deal found 12/3$225
This Frontier deal was found by Cheapflights users on 12/2. 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 12/126:11 amORD - SAT
1 stop10h 40mFrontier
Mon 12/1512:03 pmSAT - ORD
1 stop8h 14mFrontier
Deal found 12/2$228
This CheapOair deal was found by Cheapflights users on 12/1. 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 12/132:26 pmORD - SAT
1 stop17h 29mFrontier
Sun 12/141:51 pmSAT - ORD
1 stop21h 51mFrontier
Deal found 12/1$229

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 December 4, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$176
(American Airlines)

One-way from

$63
(Expedia)

Popular in

December

Cheapest in

October

Average price

$438

Good round-trip deal

$352 or less

Good one-way deal

$138 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 ($23 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 December 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 December 4, 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

MDW - SAT

MDWSAT

Chicago Midway

Mon 1/26

8:20 am-11:25 am

Nonstop3h 05m

San Antonio

Tue 1/27

2:10 pm-4:45 pm

Nonstop2h 35m

$179

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Thu 1/29

8:20 am-11:25 am

Nonstop3h 05m

San Antonio

Tue 2/3

2:10 pm-4:45 pm

Nonstop2h 35m

$179

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

Thu 1/22

9:04 am-12:24 pm

Nonstop3h 20m

San Antonio

Sun 1/25

7:00 am-9:51 am

Nonstop2h 51m

$181

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Tue 1/20

8:20 am-11:25 am

Nonstop3h 05m

San Antonio

Sat 1/24

6:35 am-1:50 pm

1 stop7h 15m

$189

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

Tue 1/6

6:15 am-12:13 pm

1 stop5h 58m

San Antonio

Sat 1/10

5:30 am-1:08 pm

1 stop7h 38m

$197

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

Tue 1/6

2:50 pm-11:23 pm

1 stop8h 33m

San Antonio

Sun 1/11

5:20 am-11:00 am

1 stop5h 40m

$199

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Fri 1/23

6:14 pm-12:38 am

1 stop6h 24m

San Antonio

Tue 1/27

4:29 pm-10:22 pm

1 stop5h 53m

$199

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Tue 1/27

10:48 am-5:22 pm

1 stop6h 34m

San Antonio

Fri 1/30

5:20 am-11:59 am

1 stop6h 39m

$199

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Sat 1/17

6:45 am-3:21 pm

1 stop8h 36m

San Antonio

Mon 1/19

5:30 am-12:46 pm

1 stop7h 16m

$199

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

Thu 1/29

6:00 am-12:45 pm

1 stop6h 45m

San Antonio

Tue 2/3

6:30 am-1:06 pm

1 stop6h 36m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
CheapOairPrice Accuracy3 starsTrust 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 CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Chicago-San Antonio flight deals on Cheapflights vs. CheapOair >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 CheapOair the most. CheapOair 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 November 28, 2025.

Booking 50 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, October is the cheapest month in which you can book a flight from Chicago to San Antonio (average of $74). Flying from Chicago to San Antonio in February is currently the most expensive (average of $183). 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 December 4, 2025.

It’s typically best to fly out from Chicago to San Antonio in the morning. Doing so could potentially save you 7% 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 November 29, 2025.

Travelers seeking maximum savings on their Chicago to San Antonio flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Sunday mornings 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 December 4, 2025.

The most flights from CHI to SAT are scheduled on a Thursday (26 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 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 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

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
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 December 4, 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
4,250 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

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
4,250 reviews
Southwest
8.0
Very good
4,250 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

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
9,066 reviews
Southwest
8.0
Very good
4,250 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

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
11,047 reviews
Southwest
8.0
Very good
4,250 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

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
8,157 reviews
Southwest
8.0
Very good
4,250 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

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
3,090 reviews
Southwest
8.0
Very good
4,250 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

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 3h 05m. 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 $125. Other airlines that can offer you cheap pricing are Spirit Airlines, from $172, and Southwest, from $203. Frontier is priced at 67% 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 $50 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $100 and American Airlines from $117 one-way.

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

    Consider Republic Airways (100%), Air Canada (86%) or United Airlines (85%) 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 $178. While the most popular route (Chicago O'Hare Intl - San Antonio) can be booked for $139 on average, our data indicates $520 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, October is the cheapest month in which you can book a flight from Chicago to San Antonio (average of $74). Flying from Chicago to San Antonio in February is currently the most expensive (average of $183). 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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$128Average$211FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$172Average$259FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$203Average$506FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$208Average$443FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$217Average$393FlexibilityNo cancel feeOn-time71%

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