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$314+ Cheap flights from Milan (MIL) 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — CHI
Nov 5 — Nov 121
Wed 11/5
Wed 11/12
1 adult, Economy
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Cheapflights Tip: The best prices from Milan to Chicago are usually found in February or March, booked 13 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

Cheap flight deals from Milan to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Milan (MIL) 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 October 6, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$566
(Mytrip)

One-way from

$314
(Mytrip)

Popular in

July

Cheapest in

February

Average price

$675

Good round-trip deal

$708 or less

Good one-way deal

$645 or less
Provider with most accurate pricing for Milan (MIL)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Milan (MIL)-Chicago (CHI) flights.
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From Milan (MIL) to Chicago (CHI)
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One-way flight from Milan (MIL) to Chicago (CHI)
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Highest demand for flights based on searches. 17% potential increase in price ($140 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Milan (MIL) to Chicago (CHI).
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Price to beat on a one-way flight from Milan (MIL) to Chicago (CHI).
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Find flight deals from Milan to Chicago

Cheapest flights from Milan to Chicago
Explore the most affordable flight options available from Milan to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 6, 2025.

This Scandinavian Airlines deal was found by Cheapflights users on 10/4. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/79:15 amMXP - ORD
1 stop14h 30mScandinavian Airlines
Fri 11/147:20 pmORD - MXP
1 stop32h 05mScandinavian Airlines
Deal found 10/4$581
This lastminute.com deal was found by Cheapflights users on 10/4. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1311:45 amLIN - ORD
1 stop13h 10mAer Lingus
Sat 11/293:50 pmORD - LIN
1 stop12h 15mAer Lingus
Deal found 10/4$585
This oojo deal was found by Cheapflights users on 10/3. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1512:55 pmLIN - ORD
2 stops34h 50mScandinavian Airlines
Thu 1/157:20 pmORD - LIN
2 stops33h 45mScandinavian Airlines
Deal found 10/3$587
This lol.travel deal was found by Cheapflights users on 10/4. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/311:15 amMXP - ORD
1 stop12h 30mScandinavian Airlines
Mon 11/107:20 pmORD - MXP
2 stops33h 50mScandinavian Airlines
Deal found 10/4$587
This lol.travel deal was found by Cheapflights users on 10/3. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/611:15 amMXP - ORD
1 stop12h 30mScandinavian Airlines
Wed 11/197:00 amORD - MXP
2 stops20h 25mScandinavian Airlines
Deal found 10/3$589
This lol.travel deal was found by Cheapflights users on 10/6. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2011:15 amMXP - ORD
1 stop12h 30mScandinavian Airlines
Thu 11/277:00 amORD - MXP
2 stops20h 25mScandinavian Airlines
Deal found 10/6$590
This Mytrip deal was found by Cheapflights users on 10/6. 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 11/204:45 pmMXP - ORD
2 stops29h 40mMultiple Airlines
Thu 11/274:51 pmORD - MXP
3 stops22h 29mMultiple Airlines
Deal found 10/6$591
This Mytrip deal was found by Cheapflights users on 10/6. 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 11/203:55 pmBGY - ORD
2 stops30h 30mMultiple Airlines
Thu 11/274:51 pmORD - BGY
3 stops22h 04mMultiple Airlines
Deal found 10/6$591
This Mytrip deal was found by Cheapflights users on 10/4. 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.
Sat 11/152:05 pmMXP - ORD
2 stops31h 40mMultiple Airlines
Fri 11/288:15 pmORD - MXP
2 stops20h 40mMultiple Airlines
Deal found 10/4$595
This Mytrip deal was found by Cheapflights users on 10/3. 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 11/63:50 pmMXP - ORD
2 stops30h 35mMultiple Airlines
Wed 11/196:48 amORD - MXP
3 stops27h 07mMultiple Airlines
Deal found 10/3$596
This Scandinavian Airlines deal was found by Cheapflights users on 10/5. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/121:00 pmMXP - ORD
2 stops34h 45mScandinavian Airlines
Wed 11/267:20 pmORD - MXP
1 stop16h 50mScandinavian Airlines
Deal found 10/5$597
This Booking.com deal was found by Cheapflights users on 10/4. 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.
Wed 11/191:00 pmMXP - ORD
2 stops34h 45mScandinavian Airlines
Wed 11/267:20 pmORD - MXP
1 stop32h 05mScandinavian Airlines
Deal found 10/4$600

Cheapflights Fare Finder

 
Customize your flight search to find flights from Milan 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 October 6, 2025.
Use the filters below to find and compare flights from Milan to Chicago that are best for you.

Fly from

Milan

Fly to

Chicago

Route

Depart

Return

Price

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Thu 11/20

3:55 pm-3:25 pm

2 stops30h 30m

Chicago O'Hare Intl

Thu 11/27

4:51 pm-9:55 pm

3 stops22h 04m

$590

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 11/20

4:45 pm-3:25 pm

2 stops29h 40m

Chicago O'Hare Intl

Thu 11/27

4:51 pm-10:20 pm

3 stops22h 29m

$591

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 11/12

1:00 pm-4:45 pm

2 stops34h 45m

Chicago O'Hare Intl

Wed 11/26

7:20 pm-7:10 pm

1 stop16h 50m

$597

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Thu 11/6

10:35 pm-3:25 pm

2 stops23h 50m

Chicago O'Hare Intl

Sun 11/16

2:31 pm-8:15 pm

3 stops22h 44m

$597

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Fri 11/7

11:15 am-4:45 pm

1 stop12h 30m

Chicago O'Hare Intl

Sun 11/23

7:20 pm-7:10 pm

1 stop16h 50m

$609

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 11/20

12:55 pm-4:45 pm

2 stops34h 50m

Chicago O'Hare Intl

Thu 11/27

7:20 pm-12:05 pm

2 stops33h 45m

$624

MilanChicago

LIN - ORD

LINORD

Milan Linate

Wed 11/12

11:45 am-5:55 pm

1 stop13h 10m

Chicago O'Hare Intl

Wed 11/26

3:50 pm-11:05 am

1 stop12h 15m

$634

MilanChicago

LIN - ORD

LINORD

Milan Linate

Tue 10/28

12:55 pm-9:05 pm

2 stops38h 10m

Chicago O'Hare Intl

Thu 11/6

7:20 pm-12:05 pm

2 stops33h 45m

$640

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Sun 11/23

7:10 am-10:35 am

3 stops34h 25m

Chicago O'Hare Intl

Sun 11/30

8:25 pm-12:15 am

2 stops20h 50m

$641

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Sun 11/2

11:25 am-5:55 pm

1 stop13h 30m

Chicago O'Hare Intl

Sun 11/9

3:50 pm-11:00 am

1 stop12h 10m

$645

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/5

Showing 1-10 of 60 results
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Compare providers for flights from Milan 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 Milan to Chicago in October.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars
AranGrantPrice 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 Milan-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Milan-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Milan-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Milan-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub 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 Milan-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 Milan to Chicago

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

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

Use this chart to determine the optimal time to book a round-trip flight from Milan to Chicago. Price data was last updated on October 3, 2025.

The price you pay for your flight from Milan to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 13 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, November is the cheapest month in which you can book a flight from Milan to Chicago (average of $484). Flying from Milan to Chicago in January is currently the most expensive (average of $868). 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 MIL to CHI?

Find hourly flight availability from Milan 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 October 6, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 30% on flights from Milan to Chicago by exploring options for tickets in the morning.

Weekly flight availability from Milan to Chicago

Explore weekly flight availability from Milan 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 October 6, 2025.

The most flights from MIL to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 on average).

The best insider tips for Milan 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 Milan to Chicago trip
Airports
MXP

For a quick departure at MXP, consider purchasing fast track security access online, available in both terminals.

Read more about MXPby Ramsey Qubein
ORD

Expect long walks to immigration at ORD's Terminal 5. Be prepared for extensive lines upon arrival.

Read more about ORDby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MXP

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 October 6, 2025.
Get a feel of what it's like to fly with United Airlines, Aer Lingus, and TAP AIR PORTUGAL from Milan to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,955 reviews

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,955 reviews
United Airlines
7.4
Good
8,955 reviews

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Aer Lingus
7.2
Good
1,313 reviews
United Airlines
7.4
Good
8,955 reviews

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
TAP AIR PORTUGAL
7.1
Good
2,003 reviews
United Airlines
7.4
Good
8,955 reviews

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Lufthansa
6.8
Okay
7,454 reviews
United Airlines
7.4
Good
8,955 reviews

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
British Airways
6.7
Okay
7,427 reviews
United Airlines
7.4
Good
8,955 reviews

Crew

8.1

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Milan to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Milan to Chicago?

    Airlines like Scandinavian Airlines, Aer Lingus, and British Airways fly from Milan to Chicago in about 13h. The time it takes to get you to your destination can typically vary by up to 21h 45m. The distance from Milan to Chicago is about 4508 mi. This flight may include one or multiple stops.

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

    Currently priced at $525, British Airways will fly you from Milan to Chicago and back. In addition to British Airways, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on United Airlines for as low as $626. British Airways is currently priced 23% below the average price you’ll pay for this route.

  • What are the most popular routes from Milan to Chicago?

    The most popular flight routes from Milan to Chicago are Milan Malpensa - Chicago O'Hare Intl, Bergamo Orio Al Serio - Chicago O'Hare Intl and Milan Linate - Chicago O'Hare Intl.

  • What are the most reliable airlines from Milan to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Milan to Chicago on time: Qatar Airways (75%), Air Canada (71%), Austrian Airlines (71%).

  • What are the cheapest flights from Milan to Chicago?

    Looking for the cheapest flight from Milan to Chicago? While on average our users pay $1,911, our data indicates the cheapest price to be $575. The most popular route (Milan Malpensa - Chicago O'Hare Intl), is priced around $505.

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

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

  • How can I find direct flights from Milan to Chicago?

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

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

    Yes. Cheapflights offers flight deals from Milan 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 Milan to Chicago?

    Currently, November is the cheapest month in which you can book a flight from Milan to Chicago (average of $484). Flying from Milan to Chicago in January is currently the most expensive (average of $868). 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
Porter
Benton Harbor
Chesterton

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Alternative routes for Milan to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Malpensa to O'Hare Intl flights
Bergamo to O'Hare Intl flights
Linate to O'Hare Intl flights
Verona to O'Hare Intl flights
Malpensa to St. Louis flights
Malpensa to Moline flights

Top 2 airlines flying from Milan to Chicago

Discover the top 2 airlines that operate flights from Milan 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 October 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
British AirwaysCheapest$525Average$716FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$626Average$952FlexibilityNo cancel feeOn-time69%

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