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$143+ 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SAT
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to San Antonio are usually found in September or August, 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 junio 12, 2025.

Round-trip from

$182
(Cheapflightsfares)

One-way from

$143
(Mytrip)

Popular in

March

Cheapest in

September

Average price

$420

Good round-trip deal

$294 or less

Good one-way deal

$188 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. 5% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in June 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 junio 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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.
dom. 6/297:27 amORD - SAT
1 stop6h 35mSpirit Airlines
mar. 7/14:20 pmSAT - ORD
1 stop13h 52mSpirit Airlines
Deal found 6/11$182
This American Airlines deal was found by Cheapflights users on 6/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/219:45 amORD - SAT
Nonstop2h 50mAmerican Airlines
mar. 10/286:28 pmSAT - ORD
Nonstop2h 57mAmerican Airlines
Deal found 6/12$217
This Southwest deal was found by Cheapflights users on 6/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/77:45 pmMDW - SAT
Nonstop2h 40mSouthwest
lun. 8/115:50 amSAT - MDW
Nonstop2h 35mSouthwest
Deal found 6/12$217
This United Airlines deal was found by Cheapflights users on 6/10. 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.
jue. 8/283:58 pmORD - SAT
1 stop6h 50mUnited Airlines
lun. 9/16:30 amSAT - ORD
Nonstop2h 59mUnited Airlines
Deal found 6/10$227
This FlightHub deal was found by Cheapflights users on 6/10. 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.
jue. 7/35:40 amORD - SAT
1 stop13h 34mMultiple Airlines
mar. 7/84:20 pmSAT - ORD
1 stop13h 43mMultiple Airlines
Deal found 6/10$234
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/215:25 pmMDW - SAT
1 stop6h 40mDelta
mar. 10/2810:45 amSAT - MDW
1 stop5h 38mDelta
Deal found 6/10$237
This Frontier deal was found by Cheapflights users on 6/11. 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.
vie. 9/126:15 amMDW - SAT
1 stop10h 25mFrontier
lun. 9/152:55 pmSAT - MDW
1 stop7h 43mFrontier
Deal found 6/11$254
This FlightHub deal was found by Cheapflights users on 6/9. 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.
mar. 6/177:00 amORD - SAT
1 stop11h 03mFrontier
mar. 6/246:59 pmSAT - ORD
1 stop29h 00mFrontier
Deal found 6/9$270
This Southwest deal was found by Cheapflights users on 6/10. 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.
mar. 9/301:50 pmORD - SAT
2 stops9h 15mSouthwest
sáb. 10/45:40 amSAT - ORD
2 stops8h 45mSouthwest
Deal found 6/10$277
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/292:00 pmORD - SAT
1 stop8h 18mDelta
mar. 8/52:49 pmSAT - ORD
1 stop6h 41mDelta
Deal found 6/10$287
This Mytrip deal was found by Cheapflights users on 6/11. 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.
vie. 7/1810:31 amMDW - SAT
2 stops38h 03mMultiple Airlines
dom. 7/207:10 amSAT - MDW
2 stops26h 31mMultiple Airlines
Deal found 6/11$308

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 junio 12, 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

dom. 6/29

7:27 am-2:02 pm

1 stop6h 35m

San Antonio

mar. 7/1

4:20 pm-6:12 am

1 stop13h 52m

$182

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

jue. 8/7

7:45 pm-10:25 pm

Nonstop2h 40m

San Antonio

lun. 8/11

5:50 am-8:25 am

Nonstop2h 35m

$217

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

jue. 8/28

3:58 pm-10:48 pm

1 stop6h 50m

San Antonio

lun. 9/1

6:30 am-9:29 am

Nonstop2h 59m

$227

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

jue. 7/3

5:40 am-7:14 pm

1 stop13h 34m

San Antonio

mar. 7/8

4:20 pm-6:03 am

1 stop13h 43m

$234

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

mar. 10/21

5:25 pm-12:05 am

1 stop6h 40m

San Antonio

mar. 10/28

10:45 am-4:23 pm

1 stop5h 38m

$237

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

vie. 9/12

6:15 am-4:40 pm

1 stop10h 25m

San Antonio

lun. 9/15

5:35 pm-11:25 pm

1 stop5h 50m

$254

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

sáb. 8/2

2:42 pm-5:38 pm

Nonstop2h 56m

San Antonio

lun. 8/4

6:28 pm-9:25 pm

Nonstop2h 57m

$268

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

mar. 6/17

7:00 am-6:03 pm

1 stop11h 03m

San Antonio

mar. 6/24

6:59 pm-11:59 pm

1 stop29h 00m

$270

ChicagoSan Antonio

ORD - SAT

ORDSAT

Chicago O'Hare Intl

mar. 7/29

2:00 pm-10:18 pm

1 stop8h 18m

San Antonio

mar. 8/5

2:49 pm-9:30 pm

1 stop6h 41m

$287

ChicagoSan Antonio

MDW - SAT

MDWSAT

Chicago Midway

vie. 7/18

10:31 am-12:34 am

2 stops38h 03m

San Antonio

dom. 7/20

7:10 am-9:41 am

2 stops26h 31m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 22 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 June 9, 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 junio 12, 2025.

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 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 June 8, 2025.

Travelers seeking maximum savings on their Chicago to San Antonio flight should consider departing on Wednesday afternoons 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 junio 12, 2025.

The most flights from CHI to SAT are scheduled on a Thursday (31 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (7 on average).

Rainfall in San Antonio by month

Plan your trip to San Antonio by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in San Antonio ranges from 1.6 - 3.7 inches per month. May is typically the wettest month, when rainfall can reach 3.7 in. December is typically the driest time to visit San Antonio when rainfall is around 1.6 in.

Temperature in San Antonio by month

Plan your trip to San Antonio by taking into account the average temperature totals by month.

If weather is an important factor for your trip to San Antonio, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 51.8 F).

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 junio 12, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United Airlines from Chicago to San Antonio by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

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.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

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
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

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
4,287 reviews

Food

7.1

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

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.
Sun Country Air
6.9
Okay
345 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

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 24 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 $182. Other airlines that can offer you cheap pricing are United Airlines, from $217, and Southwest, from $217. Spirit Airlines is priced at 54% 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 $143 on Spirit Airlines. Other airlines that offer cheap prices include Sun Country Air from $144 and American Airlines from $149 one-way.

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

    Consider United Airlines (82%), Air Canada (78%) or SkyWest Airlines (74%) 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 $182 on average our data indicates $511 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

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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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$125Average$217FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$132Average$259FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$209Average$404FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$232Average$503FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$299Average$473FlexibilityNo cancel feeOn-time69%

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