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Find Asphalt shingle roofing installers and replacers in Winnetka

Avatar for Power Home Remodeling

Power Home Remodeling

4.51(
343
)
Approved Pro

Power Home Remodeling

4.51(
343
)
Approved Pro
Customers say: Super punctual
2481 local quotes requested
34 years of experience

Does your home need replacement roofing that is high-quality, energy-efficient, and comes with a lifetime warranty? We're the nation's largest full-service exterior home remodeler and over 1000 lifetime Angi Super Service Awards. We can help transform your house into the beautiful and cost-effective home you've always dreamed of. At Power, you'll love our friendly, knowledgeable, and professional remodeling consultants and be delighted by our top-rated installation process. But don't take it from us. We've served over 1,000,000 customers across the U.S earning a 95% overall satisfaction rating. For a free, no-obligation estimate, call: (610) 990-4243 or visit https://powerhrg.com/project-quote/.

"The work was done quickly and the lead time was short."

Glenn S on November 2025

Does your home need replacement roofing that is high-quality, energy-efficient, and comes with a lifetime warranty? We're the nation's largest full-service exterior home remodeler and over 1000 lifetime Angi Super Service Awards. We can help transform your house into the beautiful and cost-effective home you've always dreamed of. At Power, you'll love our friendly, knowledgeable, and professional remodeling consultants and be delighted by our top-rated installation process. But don't take it from us. We've served over 1,000,000 customers across the U.S earning a 95% overall satisfaction rating. For a free, no-obligation estimate, call: (610) 990-4243 or visit https://powerhrg.com/project-quote/.

"The work was done quickly and the lead time was short."

Glenn S on November 2025


Avatar for Tri-Star Roofing and Construction

Tri-Star Roofing and Construction

4.50(
2
)
Approved Pro

Tri-Star Roofing and Construction

4.50(
2
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
30 years of experience

Tri-Star Roofing and Construction, is committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customers interests, and make their concerns the basis of our business.

"n/a"

Curt B on April 2022

Tri-Star Roofing and Construction, is committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customers interests, and make their concerns the basis of our business.

"n/a"

Curt B on April 2022


Home Genius Exteriors

New on HomeAdvisorNew on HomeAdvisor
Approved Pro

Home Genius Exteriors

New on HomeAdvisorNew on HomeAdvisor
Approved Pro
52 local quotes requested
22 years of experience

Elevate your home with Home Genius Exteriors, setting the standard in Cleveland by offering full-service solutions for roofing, siding, windows, doors, gutters and insulation. We support our veterans and communities by supporting local and national charitable organizations through our Home Genius Cares initiative. With an Owens Corning® Platinum Preferred designation, we also offer flexible payment options, industry leading warranties and a wide range of premium products tailored for your home. It?s time for a different experience, entrust your next home project to a genius and schedule your free inspection today!

Elevate your home with Home Genius Exteriors, setting the standard in Cleveland by offering full-service solutions for roofing, siding, windows, doors, gutters and insulation. We support our veterans and communities by supporting local and national charitable organizations through our Home Genius Cares initiative. With an Owens Corning® Platinum Preferred designation, we also offer flexible payment options, industry leading warranties and a wide range of premium products tailored for your home. It?s time for a different experience, entrust your next home project to a genius and schedule your free inspection today!


Avatar for L.E.N. Construction, Inc.

L.E.N. Construction, Inc.

4.81(
38
)
Approved Pro

L.E.N. Construction, Inc.

4.81(
38
)
Approved Pro
Customers say: Quick response
Recommended by 97% of Angi customers
Recommended by 97% of HomeAdvisor customers
27 years of experience

Len Roofing & Remodeling - We show up on time and nail it - Meticulous clean-up and respect for your property - Speed meets artistry for your complete satisfaction - We specialize in roofing, siding, windows, gutters, sheet metal & tuck-pointing. Our mission is to be acknowledged as the #1 Home Improvement Company in Chicago and the suburbs. We believe in offering a wide variety of products and educating our customers on solutions to best fit their needs. We recognize that open communication throughout the installation process is critical to our customer satisfaction. We certify our craftsmanship with the strictest quality control guidelines and personally monitor each job from start through completion.

"Fast and professional. The damage was more extensive than originally thought. L.E.N. documented everything for the insurance company and worked with me for what wasn't covered to keep my costs down."

Davis G on July 2020

Len Roofing & Remodeling - We show up on time and nail it - Meticulous clean-up and respect for your property - Speed meets artistry for your complete satisfaction - We specialize in roofing, siding, windows, gutters, sheet metal & tuck-pointing. Our mission is to be acknowledged as the #1 Home Improvement Company in Chicago and the suburbs. We believe in offering a wide variety of products and educating our customers on solutions to best fit their needs. We recognize that open communication throughout the installation process is critical to our customer satisfaction. We certify our craftsmanship with the strictest quality control guidelines and personally monitor each job from start through completion.

"Fast and professional. The damage was more extensive than originally thought. L.E.N. documented everything for the insurance company and worked with me for what wasn't covered to keep my costs down."

Davis G on July 2020


Midtown Home Improvements, Inc. (Chicago)*

4.68(
1,014
)
Approved Pro

Midtown Home Improvements, Inc. (Chicago)*

4.68(
1,014
)
Approved Pro
Customers say: Quality work
Recommended by 93% of Angi customers
Recommended by 93% of HomeAdvisor customers
34 years of experience

Midtown Home Improvements is your neighborhood home improvement specialist. Whether you are looking for energy savings with Triple Pane Windows, a new low maintenance PVC Cellular deck, a maintenance free vinyl fence, or the thickest permanent siding you can trust the experts at Midtown. We believe in providing superior products from only the finest manufacturers. Give us a call at (630) 473-4165 for more information and a free quote!

"Our deck is in severe shape. Cody is assured us we will get work done before winter so far we?ve paid >1/3 into the project &when we wanted to cancel, his boss said we would forfeit 33%. Our retirement. Being after three days of signing the contract with not 1 day sacrificed by the company we?ve caugt them in 7 ?lies/misinformations? so far. Our anxiety level is increasing as we see the concrete that will need to be poured in the winter time will be worthless making all the foundation of the deck Worthless at first we were told four days work, but then they said because of permits that it may take 2-3 weeks because of permits. They should?ve told us that in the beginning as we have mobility issues to get to our cars which will have to be moved off of property. The timing can?t be helped, but honesty can- if you?re faithful in small things, you?ll be faithful inlarge things we have to go through with the job because we can?t afford 33% of $24000. Trust is broken. Still waiting."

Jill E on November 2025

Midtown Home Improvements is your neighborhood home improvement specialist. Whether you are looking for energy savings with Triple Pane Windows, a new low maintenance PVC Cellular deck, a maintenance free vinyl fence, or the thickest permanent siding you can trust the experts at Midtown. We believe in providing superior products from only the finest manufacturers. Give us a call at (630) 473-4165 for more information and a free quote!

"Our deck is in severe shape. Cody is assured us we will get work done before winter so far we?ve paid >1/3 into the project &when we wanted to cancel, his boss said we would forfeit 33%. Our retirement. Being after three days of signing the contract with not 1 day sacrificed by the company we?ve caugt them in 7 ?lies/misinformations? so far. Our anxiety level is increasing as we see the concrete that will need to be poured in the winter time will be worthless making all the foundation of the deck Worthless at first we were told four days work, but then they said because of permits that it may take 2-3 weeks because of permits. They should?ve told us that in the beginning as we have mobility issues to get to our cars which will have to be moved off of property. The timing can?t be helped, but honesty can- if you?re faithful in small things, you?ll be faithful inlarge things we have to go through with the job because we can?t afford 33% of $24000. Trust is broken. Still waiting."

Jill E on November 2025


Midtown Home Improvements, Inc. (Chicago)

4.60(
637
)
Approved Pro

Midtown Home Improvements, Inc. (Chicago)

4.60(
637
)
Approved Pro
Customers say: Quality work
1170 local quotes requested
34 years of experience

Midtown Home Improvements is your neighborhood home improvement specialist. Whether you are looking for energy savings with Triple Pane Windows, a new low maintenance PVC Cellular deck, a maintenance free vinyl fence, or the thickest permanent siding you can trust the experts at Midtown. We believe in providing superior products from only the finest manufacturers. Give us a call at (630) 473-4165 for more information and a free quote!

"Midtown replaced all our siding and we are thrilled how it looks! Everything went smoothly from picking type and colors, scheduling, and installation. Cody and Peter watched over it all and made sure we were completely satisfied. The installers were very skilled and every detail was done by craftsmen. It turned out better than we we expected. thought it would."

Mike W on November 2025

Midtown Home Improvements is your neighborhood home improvement specialist. Whether you are looking for energy savings with Triple Pane Windows, a new low maintenance PVC Cellular deck, a maintenance free vinyl fence, or the thickest permanent siding you can trust the experts at Midtown. We believe in providing superior products from only the finest manufacturers. Give us a call at (630) 473-4165 for more information and a free quote!

"Midtown replaced all our siding and we are thrilled how it looks! Everything went smoothly from picking type and colors, scheduling, and installation. Cody and Peter watched over it all and made sure we were completely satisfied. The installers were very skilled and every detail was done by craftsmen. It turned out better than we we expected. thought it would."

Mike W on November 2025


Avatar for Pacc Building Group

Pacc Building Group

4.89(
273
)
Approved Pro

Pacc Building Group

4.89(
273
)
Approved Pro
Customers say: True professional
5 years of experience
Free onsite estimate

We focus on delivering a stress-free experience in the insurance restoration and exterior construction services. We're your trusted one-stop shop, representing property owners in the insurance claim process and delivering fair settlements. We specialize in exterior remodeling, focusing on roofing and siding. Say farewell to claim headaches and contractor searches. We handle it all, from start to finish.

"Yes the job was done professionally and done right. We are satisfied "

Henry A on June 2025

We focus on delivering a stress-free experience in the insurance restoration and exterior construction services. We're your trusted one-stop shop, representing property owners in the insurance claim process and delivering fair settlements. We specialize in exterior remodeling, focusing on roofing and siding. Say farewell to claim headaches and contractor searches. We handle it all, from start to finish.

"Yes the job was done professionally and done right. We are satisfied "

Henry A on June 2025


Rogers Roofing

New on HomeAdvisorNew on HomeAdvisor
Approved Pro

Rogers Roofing

New on HomeAdvisorNew on HomeAdvisor
Approved Pro
158 local quotes requested
58 years of experience

As experienced home improvement specialists, we seek to improve the industry’s reputation. Unlike many run-of-the-mill companies that offer undistinguished customer service and mediocre workmanship, Rogers Roofing raises the bar high. We are dedicated to providing homeowners with top-quality products and certified installation for a customer experience that’s second to none.

As experienced home improvement specialists, we seek to improve the industry’s reputation. Unlike many run-of-the-mill companies that offer undistinguished customer service and mediocre workmanship, Rogers Roofing raises the bar high. We are dedicated to providing homeowners with top-quality products and certified installation for a customer experience that’s second to none.


Avatar for Exterior Designers, LLC

Exterior Designers, LLC

4.55(
121
)
Approved Pro

Exterior Designers, LLC

4.55(
121
)
Approved Pro
Customers say: Quality work
40 local quotes requested
41 years of experience

For the last four decades, Exterior Designers Inc. (EDI) has been a trusted provider of residential exterior remodeling services throughout the suburbs of Chicago. Based in Downers Grove, Illinois, we specialize in roofing, siding, windows, doors, soffit & fascia, and gutter solutions. At EDI, you’ll never deal with pushy salespeople. Instead, you’ll work directly with the owner, Tim, for a personalized, no-pressure experience. Our team pays close attention to the details that others often miss, ensuring a final result that’s built to last and backed by service you can trust.

"I requested quotes and met with a number of companies. By far, I enjoyed meeting with John. He was informative and thorough at our meeting. Given the information provided, and our own research, I also felt as though our values matched up nicely. So much so, that we planned on using EDI services, given the quote was reasonable. However, we were never given our quote. We were strung along by a series of emails, and then received no more responses. I have tried many times to reach out for the quote, and after that, to inquire as to what happened. Again, no response at all. Now, after waiting so long, we have to start the entire process over again, and as it is October, we essentially have no hope of getting a new roof this season. I really hope our current last through the winter. This is entire unprofessional behavior, and I grow so weary of companies that make promises and do not fulfil them. We should at the very least be treated with enough respect to be given an explanation as to why they cannot or will not perform the work."

James O on September 2021

For the last four decades, Exterior Designers Inc. (EDI) has been a trusted provider of residential exterior remodeling services throughout the suburbs of Chicago. Based in Downers Grove, Illinois, we specialize in roofing, siding, windows, doors, soffit & fascia, and gutter solutions. At EDI, you’ll never deal with pushy salespeople. Instead, you’ll work directly with the owner, Tim, for a personalized, no-pressure experience. Our team pays close attention to the details that others often miss, ensuring a final result that’s built to last and backed by service you can trust.

"I requested quotes and met with a number of companies. By far, I enjoyed meeting with John. He was informative and thorough at our meeting. Given the information provided, and our own research, I also felt as though our values matched up nicely. So much so, that we planned on using EDI services, given the quote was reasonable. However, we were never given our quote. We were strung along by a series of emails, and then received no more responses. I have tried many times to reach out for the quote, and after that, to inquire as to what happened. Again, no response at all. Now, after waiting so long, we have to start the entire process over again, and as it is October, we essentially have no hope of getting a new roof this season. I really hope our current last through the winter. This is entire unprofessional behavior, and I grow so weary of companies that make promises and do not fulfil them. We should at the very least be treated with enough respect to be given an explanation as to why they cannot or will not perform the work."

James O on September 2021


Avatar for Williams Roofing & Insulation, Inc.

Williams Roofing & Insulation, Inc.

4.85(
545
)
Approved Pro

Williams Roofing & Insulation, Inc.

4.85(
545
)
Approved Pro
Super Service Award
Customers say: True professional
Recommended by 93% of Angi customers
Recommended by 93% of HomeAdvisor customers
14 local quotes requested

Why choose Williams Roofing & Insulation for your roofing needs? To start, we have decades of experience. Experience matters when protecting one of your most valuable assets, your home. We are a local, family owned and operated company serving the Chicagoland area- suburbs and surrounding areas. We are not storm chasers. We are familiar with local building codes. You know where to find us. Of course, we are licensed, insured and bonded. We offer one of the best labor warranties in the business- that's how confident we are with our craftmanship and products! We also do gutters, siding, chimneys, fascia, soffits, attic insulation and more. Quality workmanship and customer satisfaction are our top priorities. Call Williams Roofing & Insulation, Inc., today!

"Marc and his crew were great!! Marc came out and gave me an estimate the next day after I contacted him. He nspwctrd my roof and walked through what needed to be done with me. Marc provided the lowest estimate of the 4 I received and it wasn't really close. Marc's crew was able to start the replacement in less than a week and they finished the job in less than a day and a half, in spite of needing extra work. When they were done everything was cleaned up and I couldn't tell they had been here. The new roof looks great and I couldn't recommend Williams Roofing more."

Chris P on October 2025

Why choose Williams Roofing & Insulation for your roofing needs? To start, we have decades of experience. Experience matters when protecting one of your most valuable assets, your home. We are a local, family owned and operated company serving the Chicagoland area- suburbs and surrounding areas. We are not storm chasers. We are familiar with local building codes. You know where to find us. Of course, we are licensed, insured and bonded. We offer one of the best labor warranties in the business- that's how confident we are with our craftmanship and products! We also do gutters, siding, chimneys, fascia, soffits, attic insulation and more. Quality workmanship and customer satisfaction are our top priorities. Call Williams Roofing & Insulation, Inc., today!

"Marc and his crew were great!! Marc came out and gave me an estimate the next day after I contacted him. He nspwctrd my roof and walked through what needed to be done with me. Marc provided the lowest estimate of the 4 I received and it wasn't really close. Marc's crew was able to start the replacement in less than a week and they finished the job in less than a day and a half, in spite of needing extra work. When they were done everything was cleaned up and I couldn't tell they had been here. The new roof looks great and I couldn't recommend Williams Roofing more."

Chris P on October 2025

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FAQs for asphalt shingle roofing installation and replacement projects in Winnetka, IL

Roofing professionals can usually install a medium-sized asphalt shingle roof in two to three days. Installation time increases if your roof is particularly steep or difficult to access or has features like chimneys or skylights that roofers must work around.

Three-tab asphalt shingles usually have the lowest upfront cost of any roofing shingle material. They’re sturdy and typically last 15 to 20 years. However, they may have a shorter lifespan in especially hot or cold climates. Talk to a local roofing professional about the best materials for your climate. In some cases, materials with a higher upfront cost may save you more on repairs or replacements in the long run.

Start by multiplying the length by the width of your roof to calculate the square footage. Most shingle replacement costs $4 to $12 per square foot for materials and labor, depending on factors like the material and the slope of your roof. Once you know the size of your roof, you can calculate a rough estimate of total costs or contact a local roofing professional to provide you with a custom quote.

Asphalt shingles are generally considered to be a low-maintenance item. However, cleaning your asphalt roofing can help prolong the lifespan and keep it looking fresh. If you’re comfortable with DIY and have the proper equipment, you may be able to clean your asphalt shingles yourself. However, if you have an especially high or steep roof, it’s usually safer to hire a professional roof cleaner.

The Winnetka, IL homeowners’ guide to asphalt shingle roofing installations and replacements

From average costs to expert advice, get all the answers you need to get your job done.