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$82+ 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 7/13. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$235
(CheapOair)

One-way from

$82
(Mytrip)

Popular in

March

Cheapest in

August

Average price

$386

Good round-trip deal

$362 or less

Good one-way deal

$219 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. 3% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 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 San Antonio to Chicago (CHI).
Search Deals
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 June 12, 2025.

This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2710:57 pmSAT - ORD
1 stop7h 15mSpirit Airlines
Sun 6/297:27 amORD - SAT
1 stop6h 35mSpirit Airlines
Deal found 6/11$235
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.
Thu 8/72:20 pmSAT - ORD
1 stop8h 00mSouthwest
Mon 8/115:45 pmORD - SAT
1 stop5h 10mSouthwest
Deal found 6/12$237
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.
Thu 8/712:05 pmSAT - MDW
1 stop5h 30mSouthwest
Tue 8/127:05 amMDW - SAT
1 stop7h 05mSouthwest
Deal found 6/10$237
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/245:38 pmSAT - RFD
2 stops25h 41mMultiple Airlines
Sun 7/279:21 amRFD - SAT
1 stop7h 12mMultiple Airlines
Deal found 6/10$240
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.
Wed 8/276:30 amSAT - ORD
Nonstop2h 59mUnited Airlines
Mon 9/17:55 pmORD - SAT
Nonstop3h 05mUnited Airlines
Deal found 6/10$247
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/246:59 pmSAT - ORD
1 stop29h 00mMultiple Airlines
Tue 7/110:43 amORD - SAT
1 stop24h 54mMultiple Airlines
Deal found 6/12$253
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.
Fri 8/225:35 pmSAT - MDW
1 stop5h 52mFrontier
Mon 8/256:15 amMDW - SAT
1 stop10h 35mFrontier
Deal found 6/11$254
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/65:00 amSAT - ORD
1 stop8h 37mAmerican Airlines
Sat 8/99:55 amORD - SAT
Nonstop2h 47mAmerican Airlines
Deal found 6/11$260
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.
Sat 7/265:20 amSAT - MDW
1 stop7h 09mDelta
Wed 8/66:00 amMDW - SAT
1 stop5h 19mDelta
Deal found 6/10$287
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/295:35 pmSAT - ORD
1 stop6h 19mFrontier
Sun 8/3111:44 amORD - SAT
1 stop7h 49mFrontier
Deal found 6/12$298
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/46:35 pmSAT - ORD
1 stop22h 34mSun Country Air
Sun 7/66:45 amORD - SAT
1 stop27h 02mSun Country Air
Deal found 6/11$329
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.
Sat 7/265:20 amSAT - ORD
1 stop4h 56mDelta
Thu 7/315:35 amORD - SAT
1 stop5h 44mDelta
Deal found 6/10$367

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 June 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 6/27

10:57 pm-6:12 am

1 stop7h 15m

Chicago O'Hare Intl

Sun 6/29

7:27 am-2:02 pm

1 stop6h 35m

$235

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Thu 8/7

2:20 pm-10:20 pm

1 stop8h 00m

Chicago O'Hare Intl

Mon 8/11

5:45 pm-10:55 pm

1 stop5h 10m

$237

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Thu 8/7

12:05 pm-5:35 pm

1 stop5h 30m

Chicago Midway

Tue 8/12

7:05 am-2:10 pm

1 stop7h 05m

$237

San AntonioChicago

SAT - RFD

SATRFD

San Antonio

Thu 7/24

5:38 pm-7:19 pm

2 stops25h 41m

Chicago Greater Rockford

Sun 7/27

9:21 am-4:33 pm

1 stop7h 12m

$240

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Wed 8/27

6:30 am-9:29 am

Nonstop2h 59m

Chicago O'Hare Intl

Mon 9/1

7:55 pm-11:00 pm

Nonstop3h 05m

$247

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Tue 6/24

6:59 pm-11:59 pm

1 stop29h 00m

Chicago O'Hare Intl

Tue 7/1

10:43 am-11:37 am

1 stop24h 54m

$253

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 8/22

5:35 pm-11:27 pm

1 stop5h 52m

Chicago Midway

Mon 8/25

6:15 am-4:50 pm

1 stop10h 35m

$254

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Wed 8/6

5:00 am-1:37 pm

1 stop8h 37m

Chicago O'Hare Intl

Sat 8/9

9:55 am-12:42 pm

Nonstop2h 47m

$260

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Sat 7/26

5:20 am-12:29 pm

1 stop7h 09m

Chicago Midway

Wed 8/6

6:00 am-11:19 am

1 stop5h 19m

$287

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Fri 8/29

5:35 pm-11:54 pm

1 stop6h 19m

Chicago O'Hare Intl

Sun 8/31

11:44 am-7:33 pm

1 stop7h 49m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 25 results
1
2
3

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 June 9, 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 June 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 67% 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 June 8, 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 June 12, 2025.

The most flights from SAT to CHI are scheduled on a Thursday (33 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 on average).

Rainfall in Chicago by month

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

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

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

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from San Antonio to Chicago. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Entertainment

7.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 26 flights from San Antonio to Chicago per day from 6 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 $235. Other airlines that can offer you cheap pricing are Southwest, from $237, and United Airlines, from $247. These flights start at 38% 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 Spirit Airlines, with whom users have recently found tickets for as low as $82. However, be on the lookout for offers from Southwest and Frontier, 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 ANA (90%), Air Canada (85%) and United Airlines (85%).

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

    On average you can expect to pay $2,240 for a flight from San Antonio to Chicago. The cheapest flight overall is $149 while the most popular route, (San Antonio - Chicago O'Hare Intl) is currently priced at $184.

  • 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 San Antonio?

Book flights to San Antonio if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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 6 airlines flying from San Antonio to Chicago

Discover the top 6 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$111Average$260FlexibilityNo cancel feeOn-time65%
FrontierCheapest$112Average$189FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$219Average$383FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$235Average$427FlexibilityNo cancel feeOn-time63%
DeltaCheapest$241Average$437FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$285Average$463FlexibilityNo cancel feeOn-time69%

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