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$138+ 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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
SAT — CHI
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
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Cheapflights Tip: The best prices from San Antonio to Chicago are usually found in April or August, booked 82 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 April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

CheapTicketsDeal
3 stars

Round-trip from

$224
(Mytrip)

One-way from

$143
(Mytrip)

Popular in

March

Cheapest in

April

Average price

$347

Good round-trip deal

$347 or less

Good one-way deal

$232 or less
Provider with most accurate pricing for San Antonio-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for San Antonio-Chicago (CHI) flights.
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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. 1% potential increase in price ($4 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 April 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).
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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 April 17, 2025.

This Mytrip deal was found by Cheapflights users on 4/16. 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.
Fri 5/910:51 pmSAT - ORD
2 stops31h 51mSpirit Airlines
Sun 5/1110:00 amORD - SAT
1 stop26h 32mSpirit Airlines
Deal found 4/16$224
This CheapOair deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/247:36 pmSAT - ORD
1 stop28h 16mFrontier
Mon 5/265:10 amORD - SAT
1 stop6h 32mFrontier
Deal found 4/17$241
This CheapOair deal was found by Cheapflights users on 4/16. 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 4/209:13 amSAT - MDW
1 stop10h 22mFrontier
Tue 4/226:45 amMDW - SAT
1 stop10h 07mFrontier
Deal found 4/16$241
This Booking.com deal was found by Cheapflights users on 4/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2312:27 pmSAT - ORD
1 stop11h 50mMultiple Airlines
Sun 5/256:30 amORD - SAT
1 stop6h 27mMultiple Airlines
Deal found 4/16$244
This United Airlines deal was found by Cheapflights users on 4/16. 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 5/147:00 amSAT - ORD
Nonstop2h 55mUnited Airlines
Wed 5/219:00 amORD - SAT
Nonstop3h 12mUnited Airlines
Deal found 4/16$287
This Southwest deal was found by Cheapflights users on 4/16. 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 5/146:25 amSAT - MDW
Nonstop2h 35mSouthwest
Wed 5/219:15 amMDW - SAT
Nonstop2h 50mSouthwest
Deal found 4/16$287
This American Airlines deal was found by Cheapflights users on 4/17. 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.
Tue 7/16:32 amSAT - ORD
1 stop7h 13mAmerican Airlines
Tue 7/14:40 pmORD - SAT
Nonstop2h 44mAmerican Airlines
Deal found 4/17$293
This Delta deal was found by Cheapflights users on 4/16. 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.
Tue 7/16:25 amSAT - ORD
1 stop5h 38mDelta
Tue 7/15:59 pmORD - SAT
1 stop6h 18mDelta
Deal found 4/16$327
This Delta deal was found by Cheapflights users on 4/17. 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.
Tue 7/15:25 amSAT - MDW
1 stop6h 34mDelta
Tue 7/14:26 pmMDW - SAT
1 stop7h 51mDelta
Deal found 4/17$327
This Southwest deal was found by Cheapflights users on 4/16. 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.
Tue 7/1510:30 amSAT - ORD
1 stop7h 25mSouthwest
Mon 7/214:00 pmORD - SAT
2 stops7h 40mSouthwest
Deal found 4/16$372
This Mytrip deal was found by Cheapflights users on 4/16. 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 5/15:39 amSAT - MDW
3 stops28h 30mMultiple Airlines
Thu 5/82:19 pmMDW - SAT
3 stops31h 31mMultiple Airlines
Deal found 4/16$564

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 April 17, 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 5/9

10:51 pm-6:42 am

2 stops31h 51m

Chicago O'Hare Intl

Sun 5/11

10:00 am-12:32 pm

1 stop26h 32m

$224

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Sat 5/24

7:36 pm-11:52 pm

1 stop28h 16m

Chicago O'Hare Intl

Mon 5/26

5:10 am-11:42 am

1 stop6h 32m

$241

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Fri 5/23

12:27 pm-12:17 am

1 stop11h 50m

Chicago O'Hare Intl

Sun 5/25

6:30 am-12:57 pm

1 stop6h 27m

$244

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Fri 5/23

12:27 pm-10:14 pm

1 stop9h 47m

Chicago Midway

Sun 5/25

9:12 pm-9:47 am

1 stop12h 35m

$250

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Tue 7/1

6:32 am-1:45 pm

1 stop7h 13m

Chicago O'Hare Intl

Tue 7/1

4:40 pm-7:24 pm

Nonstop2h 44m

$267

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Wed 5/14

7:00 am-9:55 am

Nonstop2h 55m

Chicago O'Hare Intl

Wed 5/21

9:00 am-12:12 pm

Nonstop3h 12m

$287

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Wed 5/14

6:25 am-9:00 am

Nonstop2h 35m

Chicago Midway

Wed 5/21

9:15 am-12:05 pm

Nonstop2h 50m

$287

San AntonioChicago

SAT - RFD

SATRFD

San Antonio

Thu 5/8

11:42 am-8:46 pm

1 stop9h 04m

Chicago Greater Rockford

Sun 5/18

12:28 pm-5:04 am

1 stop16h 36m

$299

San AntonioChicago

SAT - ORD

SATORD

San Antonio

Tue 7/1

6:25 am-12:03 pm

1 stop5h 38m

Chicago O'Hare Intl

Tue 7/1

5:59 pm-12:17 am

1 stop6h 18m

$327

San AntonioChicago

SAT - MDW

SATMDW

San Antonio

Tue 7/1

5:25 am-11:59 am

1 stop6h 34m

Chicago Midway

Tue 7/1

4:26 pm-12:17 am

1 stop7h 51m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 26 results
1
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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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy1 starTrust 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Antonio-Chicago flight deals on Cheapflights vs. FlightHub >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 CheapTicketsDeal the most. CheapTicketsDeal 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.

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
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
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
Airports
SAT

SAT's central ticketing area simplifies check-in. After security, explore diverse dining options in Terminals A and B without needing to re-clear security.

Read more about SATby Ramsey Qubein
ORD

Upon arrival at ORD, consider taking the 'L' train for a quick and cost-effective trip to downtown Chicago, avoiding potential traffic delays.

Read more about ORDby Ramsey Qubein
Our travel experts
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
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
Ramsey Qubein

Ramsey Qubein

Expert on ORD 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 April 11, 2025.

To ensure you get the cheapest price possible for a flight from San Antonio to Chicago, you should look to book at least 82 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 April 17, 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 68% 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 March 30, 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 April 17, 2025.

The most flights from SAT to CHI are scheduled on a Wednesday (34 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 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 April 17, 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
9,882 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,882 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,917 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,667 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 29 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 $224. Other airlines that can offer you cheap pricing are Frontier, from $241, and United Airlines, from $287. These flights start at 41% 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 $143. However, be on the lookout for offers from American 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 Qatar Airways (92%), Japan Airlines (92%) and Emirates (84%).

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

    On average you can expect to pay $915 for a flight from San Antonio to Chicago. The cheapest flight overall is $164 while the most popular route, (San Antonio - Chicago O'Hare Intl) is currently priced at $169.

  • 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
Hammond
Benton Harbor
Porter
Lansing
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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$111Average$244FlexibilityNo cancel feeOn-time65%
FrontierCheapest$112Average$210FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$222Average$427FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$246Average$396FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$290Average$468FlexibilityNo cancel feeOn-time69%
DeltaCheapest$301Average$437FlexibilityNo cancel feeOn-timeN/A

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