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$64+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — CHI
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Find cheap flights from San Antonio to Chicago with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from San Antonio to Chicago are usually found in September or August, booked 70 days in advance, depart on a Thursday or Friday and return on a Tuesday

Cheap 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 December 12, 2025.

This Priceline deal was found by Cheapflights users on 12/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/242:09 pmSAT - ORD
1 stop10h 03mFrontier
Wed 12/3111:23 amORD - SAT
1 stop6h 53mFrontier
Deal found 12/10$208
This Expedia deal was found by Cheapflights users on 12/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:11 pmSAT - MDW
1 stop26h 47mFrontier
Wed 12/316:12 amMDW - SAT
1 stop10h 49mFrontier
Deal found 12/11$217
This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/242:09 pmSAT - ORD
1 stop10h 03mFrontier
Sun 1/410:49 pmORD - SAT
1 stop14h 27mFrontier
Deal found 12/10$228
This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:11 pmSAT - MDW
1 stop26h 47mFrontier
Tue 12/303:10 pmMDW - SAT
1 stop27h 06mFrontier
Deal found 12/10$233
This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:45 amSAT - ORD
1 stop17h 27mFrontier
Sun 1/410:49 pmORD - SAT
1 stop14h 27mFrontier
Deal found 12/10$237
This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:11 pmSAT - MDW
1 stop26h 47mFrontier
Sun 1/410:50 pmMDW - SAT
1 stop25h 27mFrontier
Deal found 12/10$237
This Frontier deal was found by Cheapflights users on 12/11. 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.
Wed 12/242:09 pmSAT - ORD
1 stop10h 03mFrontier
Thu 1/17:00 amORD - SAT
1 stop6h 14mFrontier
Deal found 12/11$253
This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:45 amSAT - ORD
1 stop17h 27mFrontier
Sun 1/410:49 pmORD - SAT
1 stop14h 27mFrontier
Deal found 12/10$258
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Wed 12/242:08 pmSAT - ORD
Nonstop2h 52mUnited Airlines
Wed 12/313:35 pmORD - SAT
Nonstop3h 09mUnited Airlines
Deal found 12/10$261
This Southwest deal was found by Cheapflights users on 12/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/242:30 pmSAT - MDW
Nonstop2h 35mSouthwest
Wed 12/314:55 pmMDW - SAT
Nonstop2h 55mSouthwest
Deal found 12/11$261
This CheapOair deal was found by Cheapflights users on 12/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 amSAT - ORD
1 stop17h 27mFrontier
Fri 1/26:00 amORD - SAT
1 stop11h 01mFrontier
Deal found 12/10$274
This CheapOair deal was found by Cheapflights users on 12/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/216:45 amSAT - MDW
1 stop15h 05mFrontier
Wed 12/248:15 amMDW - SAT
1 stop8h 46mFrontier
Deal found 12/9$279

Find 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 December 12, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$185
(Cheapflightsfares)

One-way from

$64
(Frontier)

Popular in

December

Cheapest in

September

Average price

$439

Good round-trip deal

$379 or less

Good one-way deal

$225 or less
Provider with most accurate pricing for San Antonio-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Antonio-Chicago (CHI) flights.
Search Deals
From San Antonio to Chicago (CHI)
Search Deals
One-way flight from San Antonio to Chicago (CHI)
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 ($6 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 San Antonio to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from San Antonio to Chicago (CHI).
Search Deals

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 December 12, 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

Fri 1/30

6:13 pm-5:52 pm

2 stops23h 39m

Chicago O'Hare Intl

Sun 2/1

8:43 pm-9:40 am

1 stop12h 57m

$203

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Tue 1/6

12:45 pm-7:02 pm

1 stop6h 17m

Chicago O'Hare Intl

Tue 1/13

10:48 am-11:52 pm

1 stop13h 04m

$236

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Wed 3/4

5:12 pm-2:05 pm

2 stops20h 53m

Chicago O'Hare Intl

Tue 3/10

7:59 pm-9:30 am

1 stop13h 31m

$242

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Wed 12/24

6:40 am-9:31 am

Nonstop2h 51m

Chicago O'Hare Intl

Wed 12/31

3:35 pm-6:44 pm

Nonstop3h 09m

$261

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 12/24

2:30 pm-5:05 pm

Nonstop2h 35m

Chicago Midway

Wed 12/31

4:55 pm-7:50 pm

Nonstop2h 55m

$261

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Tue 1/6

2:05 pm-4:57 pm

Nonstop2h 52m

Chicago O'Hare Intl

Tue 1/13

8:00 pm-11:13 pm

Nonstop3h 13m

$277

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 1/17

6:00 am-8:35 am

Nonstop2h 35m

Chicago Midway

Sun 1/18

2:35 pm-11:05 pm

1 stop8h 30m

$277

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Tue 1/6

2:10 pm-4:45 pm

Nonstop2h 35m

Chicago Midway

Tue 1/13

8:20 am-11:25 am

Nonstop3h 05m

$277

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 1/17

4:29 pm-10:07 pm

1 stop5h 38m

Chicago Midway

Sun 1/18

6:45 am-12:45 pm

1 stop6h 00m

$281

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 1/7

5:45 am-1:55 pm

2 stops8h 10m

Chicago Midway

Wed 1/14

8:20 am-11:25 am

Nonstop3h 05m

$292

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 50 results
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Compare providers for flights from San Antonio to Chicago

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 San Antonio to Chicago in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
JustAirTicketPrice Accuracy-Trust Score*1 star
PricelinePrice Accuracy1 starTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice 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 San Antonio-Chicago flights, users find the pricing of Justfly.com to be most consistent on Cheapflights vs. Justfly.com Users can find the same prices on San Antonio-Chicago flight deals on Cheapflights vs. Justfly.com >95% of the time. Price accuracy is based on data collected from San Antonio-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Antonio-Chicago flights, Cheapflights users trust Justfly.com the most. Justfly.com 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 San Antonio-Chicago 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 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 December 5, 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, March is the cheapest month in which you can book a flight from San Antonio to Chicago (average of $58). Flying from San Antonio to Chicago in February is currently the most expensive (average of $160). 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 December 12, 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 64% versus a flight at noon.

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 December 12, 2025.

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

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 60% 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.

Atlanta (ATL) is the most affordable 1-stop option, with an average round-trip price of $173.

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.

The best insider tips for San Antonio to Chicago 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 San Antonio to Chicago trip
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
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 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 December 12, 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
7.9
Good
4,253 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Food

7.0

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
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Food

7.0

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
9,095 reviews
Southwest
7.9
Good
4,253 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Food

7.0

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
11,050 reviews
Southwest
7.9
Good
4,253 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Food

7.0

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
8,179 reviews
Southwest
7.9
Good
4,253 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Food

7.0

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
3,084 reviews
Southwest
7.9
Good
4,253 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Food

7.0

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 20 flights from San Antonio to Chicago per day from 5 different airlines.

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

    Spirit Airlines, United Airlines, and Southwest can get you from San Antonio to Chicago in just under 2h 35m. Your travel time can differ by up to 3h 42m. San Antonio and Chicago are separated by a distance of 1036 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $96. Other airlines that can offer you cheap pricing are Spirit Airlines, from $191, and American Airlines, from $235. These flights start at 74% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from San Antonio to Chicago one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $73. However, be on the lookout for offers from Spirit Airlines and Southwest, as they are both options that can get you from San Antonio to Chicago for a low price.

  • 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 Republic Airways (100%), Royal Jordanian (86%) and Qatar Airways (86%).

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

    On average you can expect to pay $993 for a flight from San Antonio to Chicago. The cheapest flight overall is $129 while the most popular route, (San Antonio - Chicago O'Hare Intl) is currently priced at $153.

  • 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, March is the cheapest month in which you can book a flight from San Antonio to Chicago (average of $58). Flying from San Antonio to Chicago in February is currently the most expensive (average of $160). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$97Average$216FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$208Average$302FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$235Average$389FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$256Average$425FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$287Average$458FlexibilityNo cancel feeOn-time69%

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