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$100+ Cheap flights from San Antonio (SAT) to Chicago (CHI)

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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — CHI
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from San Antonio to Chicago are usually found in August or September, booked 70 days in advance, depart on a Thursday or Friday and return on a Wednesday

Cheap flight deals from San Antonio to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from San Antonio (SAT) to Chicago (CHI). 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 August 14, 2025.

Round-trip from

$201
(Expedia)

One-way from

$100
(Mytrip)

Popular in

March

Cheapest in

August

Average price

$285

Good round-trip deal

$275 or less

Good one-way deal

$149 or less
From San Antonio to Chicago (CHI)
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One-way flight from San Antonio to Chicago (CHI)
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Highest demand for flights based on searches. 5% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from San Antonio to Chicago (CHI).
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Price to beat on a one-way flight from San Antonio to Chicago (CHI).
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Find flight deals from San Antonio to Chicago

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

This Expedia deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/56:00 amSAT - ORD
1 stop11h 04mMultiple Airlines
Fri 11/75:11 amORD - SAT
1 stop11h 29mMultiple Airlines
Deal found 8/14$201
This Cheapflightsfares deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/812:45 pmSAT - ORD
1 stop9h 13mSpirit Airlines
Wed 9/1011:15 amORD - SAT
1 stop9h 37mSpirit Airlines
Deal found 8/12$203
This Frontier deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1811:33 amSAT - MDW
1 stop11h 47mFrontier
Sat 9/2010:51 amMDW - SAT
2 stops22h 19mFrontier
Deal found 8/14$203
This Cheapflightsfares deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/86:00 amSAT - ORD
1 stop11h 04mSpirit Airlines
Mon 11/1010:18 amORD - SAT
1 stop12h 09mSpirit Airlines
Deal found 8/12$206
This Priceline deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/185:32 pmSAT - ORD
1 stop6h 21mFrontier
Sat 10/257:15 amORD - SAT
1 stop9h 22mFrontier
Deal found 8/12$207
This Priceline deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/182:54 pmSAT - ORD
1 stop7h 04mMultiple Airlines
Sat 9/208:25 amORD - SAT
1 stop6h 02mMultiple Airlines
Deal found 8/12$208
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/101:44 pmSAT - ORD
1 stop8h 01mAmerican Airlines
Wed 9/1711:54 amORD - SAT
1 stop8h 57mAmerican Airlines
Deal found 8/13$209
This Priceline deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/35:35 pmSAT - ORD
1 stop6h 24mFrontier
Sat 11/87:20 amORD - SAT
1 stop7h 54mFrontier
Deal found 8/12$210
This FlightHub deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/179:47 pmSAT - ORD
1 stop14h 04mMultiple Airlines
Mon 9/226:00 amORD - SAT
1 stop13h 15mMultiple Airlines
Deal found 8/14$211
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/169:47 pmSAT - ORD
2 stops20h 27mSpirit Airlines
Sat 9/2012:46 pmORD - SAT
1 stop8h 06mSpirit Airlines
Deal found 8/12$212
This Cheapflightsfares deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/182:54 pmSAT - ORD
1 stop7h 04mSpirit Airlines
Sat 9/2012:46 pmORD - SAT
1 stop8h 06mSpirit Airlines
Deal found 8/12$213
This Frontier deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1811:33 amSAT - ORD
2 stops11h 47mFrontier
Mon 9/225:10 amORD - SAT
1 stop11h 20mFrontier
Deal found 8/14$214

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Antonio to Chicago 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 August 14, 2025.
Use the filters below to find and compare flights from San Antonio to Chicago that are best for you.

Fly from

San Antonio

Fly to

Chicago

Route

Depart

Return

Price

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Wed 11/5

6:00 am-5:04 pm

1 stop11h 04m

Chicago O'Hare Intl

Fri 11/7

5:11 am-4:40 pm

1 stop11h 29m

$201

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Sat 9/13

8:37 pm-11:59 am

1 stop15h 22m

Chicago O'Hare Intl

Sat 9/20

12:46 pm-8:52 pm

1 stop8h 06m

$203

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 9/18

11:33 am-11:20 pm

1 stop11h 47m

Chicago Midway

Sat 9/20

10:51 am-9:10 am

2 stops22h 19m

$203

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Mon 9/8

12:45 pm-9:58 pm

1 stop9h 13m

Chicago O'Hare Intl

Wed 9/10

11:15 am-8:52 pm

1 stop9h 37m

$203

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Sat 11/8

6:00 am-5:04 pm

1 stop11h 04m

Chicago O'Hare Intl

Mon 11/10

10:18 am-10:27 pm

1 stop12h 09m

$206

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Sat 10/18

5:32 pm-11:53 pm

1 stop6h 21m

Chicago O'Hare Intl

Sat 10/25

7:15 am-4:37 pm

1 stop9h 22m

$207

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Sat 10/18

5:32 pm-11:53 pm

1 stop6h 21m

Chicago O'Hare Intl

Tue 10/21

7:15 am-3:14 pm

1 stop7h 59m

$207

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Tue 10/14

3:59 pm-11:53 pm

1 stop7h 54m

Chicago O'Hare Intl

Wed 10/15

7:15 am-3:14 pm

1 stop7h 59m

$207

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Sat 9/27

3:22 pm-9:28 pm

1 stop6h 06m

Chicago O'Hare Intl

Tue 9/30

9:00 am-8:52 pm

1 stop11h 52m

$208

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Thu 9/18

2:54 pm-9:58 pm

1 stop7h 04m

Chicago O'Hare Intl

Sat 9/20

8:25 am-2:27 pm

1 stop6h 02m

$208

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 45 results
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The best insider tips for San Antonio to Chicago 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 San Antonio to Chicago trip
Airlines
Southwest

Enjoy free snacks and non-alcoholic drinks, plus in-flight entertainment on your device.


Two free checked bags included, even oversized items like skis or golf clubs.

Read more about Southwestby Marisa Garcia
United Airlines

Basic Economy allows a personal item only; no carry-on bags permitted.


Prepay checked bags 24 hours before to save on fees.

Read more about United Airlinesby Harriet Baskas
Airports
SAT

Parking at SAT is convenient with a new seven-story garage and economy lots offering shuttle service for longer trips.

Read more about SATby Ramsey Qubein
ORD

For a quick city transfer, take the “L” train from ORD to downtown Chicago, avoiding potential traffic delays.

Read more about ORDby Ramsey Qubein
MDW

The Orange Line train connects MDW to downtown Chicago in under 30 minutes, offering a cost-effective travel option.

Read more about MDWby Ramsey Qubein
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
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 San Antonio to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from San Antonio 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 San Antonio to Chicago

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

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

To ensure you get the cheapest price possible for a flight from San Antonio to Chicago, you should look to book at least 70 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, August is the cheapest month in which you can book a flight from San Antonio to Chicago (average of $245). Flying from San Antonio to Chicago in March is currently the most expensive (average of $321). 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 SAT to CHI?

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

When flying from San Antonio to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 69% versus a flight at noon.

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

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

Travelers seeking maximum savings on their San Antonio to Chicago flight should consider departing on Friday evenings 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 San Antonio to Chicago

Explore weekly flight availability from San Antonio to Chicago. 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 August 14, 2025.

The most flights from SAT to CHI are scheduled on a Thursday (33 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (15 on average).

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

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

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

Orlando (MCO) – chosen by Cheapflights users on 75% of 1-stop itineraries from San Antonio to Chicago on Cheapflights.

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

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

Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of $287.

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

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

Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 10h 05m.

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

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

Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 3h 12m.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated August 14, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and American Airlines from San Antonio to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

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
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

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
8,916 reviews
Southwest
8.0
Very good
4,244 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

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
4,244 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

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.
Spirit Airlines
6.3
Okay
8,045 reviews
Southwest
8.0
Very good
4,244 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

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.
Frontier
5.8
Fair
3,219 reviews
Southwest
8.0
Very good
4,244 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

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 San Antonio to Chicago. 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 from for flights from San Antonio to Chicago?

    If you book a flight to Chicago from San Antonio, you will be flying from San Antonio, which is the city’s only airport. San Antonio (SAT) is located 7.6 mi from the center of San Antonio. There are 24 flights from San Antonio to Chicago per day from 5 different airlines.

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

    Cheapflights users have booked flights from San Antonio to Chicago round-trip from $111. Other airlines that can offer you cheap pricing are Frontier, from $114, and American Airlines, from $208. These flights start at 70% lower than the current average price 3 months from now.

  • What are the most popular routes from San Antonio to Chicago?

    When deciding which route to take from San Antonio to Chicago consider San Antonio - Chicago O'Hare Intl, San Antonio - Chicago Midway or San Antonio - Chicago Greater Rockford as they are the most popular.

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

    The top 3 most reliable airlines when flying from San Antonio to Chicago are Aer Lingus (83%), ANA (82%) and Emirates (79%).

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

    On average you can expect to pay $896 for a flight from San Antonio to Chicago. The cheapest flight overall is $117 while the most popular route, (San Antonio - Chicago O'Hare Intl) is currently priced at $175.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from San Antonio to Chicago 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 San Antonio to Chicago?

    Currently, August is the cheapest month in which you can book a flight from San Antonio to Chicago (average of $245). Flying from San Antonio to Chicago in March is currently the most expensive (average of $321). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for San Antonio to Chicago

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

Discover the top 5 airlines that operate flights from San Antonio to Chicago. 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$111Average$302FlexibilityNo cancel feeOn-time65%
FrontierCheapest$114Average$201FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$208Average$386FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$245Average$436FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$283Average$491FlexibilityNo cancel feeOn-time69%

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