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TRUSTED BY CRESTWOOD, IL HOMEOWNERS

  • Average homeowner rating star icon4.5
    Average homeowner rating
  • Verified reviews icon556
    Verified roofing services reviews

Find Roofers in Crestwood

Avatar for Kross Town Roofing & Siding, LLC

Kross Town Roofing & Siding, LLC

4.92(
76
)
Approved Pro

Kross Town Roofing & Siding, LLC

4.92(
76
)
Approved Pro
Super Service Award
Customers say: Quick response
Recommended by 90% of Angi customers
Recommended by 90% of HomeAdvisor customers
16 years of experience

We pride our company on reliability, great communication, integrity, and quality work. We strongly believe in giving our absolute best in all of our projects, no matter how big or small they may be. We are experts in our trade, and will always keep you educated on your particular task or project. We look forward to earning your business!

"Chris was amazing. He was puntual, Professional and thorough. My gutters were impacted in some áreas and just needed attention in others. He took photos and showed me the issues. I highly recommend Kross Town Roofing and Siding, LLC"

Sandra B on August 2025

We pride our company on reliability, great communication, integrity, and quality work. We strongly believe in giving our absolute best in all of our projects, no matter how big or small they may be. We are experts in our trade, and will always keep you educated on your particular task or project. We look forward to earning your business!

"Chris was amazing. He was puntual, Professional and thorough. My gutters were impacted in some áreas and just needed attention in others. He took photos and showed me the issues. I highly recommend Kross Town Roofing and Siding, LLC"

Sandra B on August 2025


Avatar for Bob the Builder Inc

Bob the Builder Inc

4.95(
132
)
Approved Pro

Bob the Builder Inc

4.95(
132
)
Approved Pro
Customers say: Quick response
Recommended by 97% of Angi customers
Recommended by 97% of HomeAdvisor customers
53 years of experience

Now offering FREE Roof Inspections to establish WIND and HAIL damage. Proud winner of the 2013, 2014, 2015, 2016, 2017, 2018 and recently the 2019 Super Service Award. I personally supervise every job to insure that my clients vision becomes a reality.

"Bob the Builder Inc. is an excellent company. They are professional and do outstanding work. Wes came to my home and checked out my roof damage quickly. tom walked me through the filing of an insurance claim. Robert their Master carpenter and his crew does excellent work. Their crew quickly and thoroughly gave me a new roof, gutters, vents and a solar attic fan. I was impressed how clean they left my property everything was hauled away. I would not hesitate to use them again in fixing or remodeling my home. "

Linda P on January 2026

Now offering FREE Roof Inspections to establish WIND and HAIL damage. Proud winner of the 2013, 2014, 2015, 2016, 2017, 2018 and recently the 2019 Super Service Award. I personally supervise every job to insure that my clients vision becomes a reality.

"Bob the Builder Inc. is an excellent company. They are professional and do outstanding work. Wes came to my home and checked out my roof damage quickly. tom walked me through the filing of an insurance claim. Robert their Master carpenter and his crew does excellent work. Their crew quickly and thoroughly gave me a new roof, gutters, vents and a solar attic fan. I was impressed how clean they left my property everything was hauled away. I would not hesitate to use them again in fixing or remodeling my home. "

Linda P on January 2026


Avatar for Guardian Roofing Systems, LLC

Guardian Roofing Systems, LLC

4.92(
61
)
Approved Pro

Guardian Roofing Systems, LLC

4.92(
61
)
Approved Pro
Super Service Award
Customers say: Quick response
Recommended by 93% of Angi customers
Recommended by 93% of HomeAdvisor customers
16 years of experience

Guardian Roofing Systems, LLC is a locally owned and operated company that values honesty and integrity and treats your home or business as if it were our own. Licensed, Bonded, Insured and all work is guaranteed. So if you decide on Guardian Roofing Systems LLC for your next project you have peace of mind that's its going to be done right. With 25 years of experience, we offer a verity of services that are customizable to each individual project. You will find us to be competitively priced, paying close attention to the details of every project, and offer informative photo updates so you see the progress of new installations or repairs step by step, even answering questions and addressing concerns along the way. We look forward to building lasting relationships and guarantee your satisfaction!

"They completed the job on time and within the agreed estimate. I just had work completed and it has not been tested by rain/snow but the workmanship looks great."

Gregory C on September 2025

Guardian Roofing Systems, LLC is a locally owned and operated company that values honesty and integrity and treats your home or business as if it were our own. Licensed, Bonded, Insured and all work is guaranteed. So if you decide on Guardian Roofing Systems LLC for your next project you have peace of mind that's its going to be done right. With 25 years of experience, we offer a verity of services that are customizable to each individual project. You will find us to be competitively priced, paying close attention to the details of every project, and offer informative photo updates so you see the progress of new installations or repairs step by step, even answering questions and addressing concerns along the way. We look forward to building lasting relationships and guarantee your satisfaction!

"They completed the job on time and within the agreed estimate. I just had work completed and it has not been tested by rain/snow but the workmanship looks great."

Gregory C on September 2025


Avatar for Trela Roofing and Remodeling

Trela Roofing and Remodeling

4.81(
979
)
Approved Pro

Trela Roofing and Remodeling

4.81(
979
)
Approved Pro
Customers say: Quality work
Recommended by 94% of Angi customers
Recommended by 94% of HomeAdvisor customers
74 years of experience

Trela Roofing & Remodeling. 64 years in business, 3 Generations. Tens of thousands of customers. Over 1,300 Total Reviews on Angie's List, We have earned Super Service Award Eight Years in a row, also Angie's List Super Service Awards in Multiple Service Categories. BBB A+ Rating. Yelp. We us no sub contractors, only our own employees, trained by us and our manufacturers. All roofing is hand nailed. We accept Major Credit Cards.

"Best company I have hired since I began renovating my home. Ryan is professional, the company acts quickly, and the work is of quality."

Patrick G on July 2024

Trela Roofing & Remodeling. 64 years in business, 3 Generations. Tens of thousands of customers. Over 1,300 Total Reviews on Angie's List, We have earned Super Service Award Eight Years in a row, also Angie's List Super Service Awards in Multiple Service Categories. BBB A+ Rating. Yelp. We us no sub contractors, only our own employees, trained by us and our manufacturers. All roofing is hand nailed. We accept Major Credit Cards.

"Best company I have hired since I began renovating my home. Ryan is professional, the company acts quickly, and the work is of quality."

Patrick G on July 2024


Avatar for Rogers Roofing

Rogers Roofing

4.74(
99
)
Approved Pro

Rogers Roofing

4.74(
99
)
Approved Pro
Customers say: True professional
58 years of experience
Free onsite estimate

With more than 50 years of industry experience, we offer professional knowledge and expertise that homeowners depend on. That's why we are one of the most referred roofing contractors serving Hammond and surrounding areas in Northwest Indiana and Chicagoland. Our long track record of successful projects, from roof replacement to siding installation, and more, inspire total confidence, and customers know they can trust us to provide reliable products and consistently meticulous workmanship.

"I regret hiring this company. The sales rep was pushy and misleading about what was included ? I believed gutters, soffit, and fascia were part of the job, but later was told it was just a cleaning (which never happened). The crew left open holes in my roof on day one, and the ?one-day job? dragged into four days of loud, late work with sloppy cleanup and debris left behind. When they said the job was done, I found exposed nail heads, poor trim work, and granule loss on my brand-new roof. They had to send crews back multiple times, and I still had to hire two independent inspectors at my own expense. I was also charged over $1,000 extra for wood and for trim I didn?t want ? now I?ll have to pay to remove and replace it. Despite repeated promises from management that they would ?take care of me,? my calls, emails, texts, and photos went ignored after one brief call from the GM. Poor workmanship, poor communication, and no accountability. I would not recommend this company."

Vicky V on September 2025

With more than 50 years of industry experience, we offer professional knowledge and expertise that homeowners depend on. That's why we are one of the most referred roofing contractors serving Hammond and surrounding areas in Northwest Indiana and Chicagoland. Our long track record of successful projects, from roof replacement to siding installation, and more, inspire total confidence, and customers know they can trust us to provide reliable products and consistently meticulous workmanship.

"I regret hiring this company. The sales rep was pushy and misleading about what was included ? I believed gutters, soffit, and fascia were part of the job, but later was told it was just a cleaning (which never happened). The crew left open holes in my roof on day one, and the ?one-day job? dragged into four days of loud, late work with sloppy cleanup and debris left behind. When they said the job was done, I found exposed nail heads, poor trim work, and granule loss on my brand-new roof. They had to send crews back multiple times, and I still had to hire two independent inspectors at my own expense. I was also charged over $1,000 extra for wood and for trim I didn?t want ? now I?ll have to pay to remove and replace it. Despite repeated promises from management that they would ?take care of me,? my calls, emails, texts, and photos went ignored after one brief call from the GM. Poor workmanship, poor communication, and no accountability. I would not recommend this company."

Vicky V on September 2025


"Fast installation, great crew."

Lynn O on January 2021

With several years experience, we work hard to bring each customer the best possible service and quality available. We look forward to working with you on your next project. We welcome your questions and thank you for your interest.

"Fast installation, great crew."

Lynn O on January 2021


Avatar for Montes Roofing, LLC

Montes Roofing, LLC

4.78(
94
)
Approved Pro

Montes Roofing, LLC

4.78(
94
)
Approved Pro
Customers say: True professional
Recommended by 92% of Angi customers
Recommended by 92% of HomeAdvisor customers
56 years of experience

At Montes Roofing, we don’t just build roofs—we build trust. From expert craftsmanship to a rock-solid commitment to excellence, our team delivers results you can see and feel from start to finish. Whether it’s a new installation or a repair, we take pride in doing it right the first time. Got questions? Reach out today—we’re here to help protect what matters most!

"Great job completed everything on time "

Dean S on August 2025

At Montes Roofing, we don’t just build roofs—we build trust. From expert craftsmanship to a rock-solid commitment to excellence, our team delivers results you can see and feel from start to finish. Whether it’s a new installation or a repair, we take pride in doing it right the first time. Got questions? Reach out today—we’re here to help protect what matters most!

"Great job completed everything on time "

Dean S on August 2025


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


Avatar for Faithful Roofing & Masonry

Faithful Roofing & Masonry

5.00(
13
)
Approved Pro

Faithful Roofing & Masonry

5.00(
13
)
Approved Pro
Customers say: Quick response
Free onsite estimate
Emergency services offered

Faithful roofing and Masonary is a full-service roofing contractor that provides quality roof repair, replacement, and restoration services to homeowners and businesses in the Chicago area. We have years of experience repairing and replacing roofs damaged by storms, weather conditions, and other factors. We are also experts at handling insurance claims related to roof damage. Our team can inspect your property quickly and provide a detailed estimate for the necessary repairs. We are dedicated to providing our customers with the best possible service and products. We offer a satisfaction guarantee on all of our work. If you are not completely satisfied with our work, we will make it right.

"Service was done and will come back in the spring to complete job"

Lilmon W on December 2025

Faithful roofing and Masonary is a full-service roofing contractor that provides quality roof repair, replacement, and restoration services to homeowners and businesses in the Chicago area. We have years of experience repairing and replacing roofs damaged by storms, weather conditions, and other factors. We are also experts at handling insurance claims related to roof damage. Our team can inspect your property quickly and provide a detailed estimate for the necessary repairs. We are dedicated to providing our customers with the best possible service and products. We offer a satisfaction guarantee on all of our work. If you are not completely satisfied with our work, we will make it right.

"Service was done and will come back in the spring to complete job"

Lilmon W on December 2025


Avatar for J & B West Roofing & Construction

J & B West Roofing & Construction

4.74(
94
)
Approved Pro

J & B West Roofing & Construction

4.74(
94
)
Approved Pro
Customers say: Quality work
Recommended by 91% of Angi customers
Recommended by 91% of HomeAdvisor customers
19 years of experience

Voted "Best Contractor" by readers of the LaPorte Herald-Argus in 2013 and 2015, Angie's List 2017, and South Bend Tribune Reader's Choice winner, we are honored to continue serving our local communities. We proudly hold the only Owens Corning Platinum Preferred and James Hardie Elite status in Northern Indiana and Southwest Michigan. If you need roofing, siding, gutters or windows, JB West is the exterior remodeling contractor for you! Our company started in 2007 when two brothers started doing roofing and construction jobs and built a reputation for quality and service. A majority of our work comes from happy customer referrals and we have an appreciation program to thank them for their support. We proudly serve LaPorte, Marshall, Porter, St. Joseph and Starke counties in Northwest Indiana and Berrien, Cass Van Buren and Saint Joseph counties in Southwest Michigan. Call 219-363-6151 today for your free estimate!

"I recently had a new roof installed by JB West and was thoroughly impressed with the entire experience. George and Brian were especially helpful throughout the process, providing insurance information and references before I even had to ask. Their communication made everything smooth and stress-free. The install crew was professional, efficient, and completed the job quickly with excellent workmanship. I appreciated the no-pressure approach and how responsive the entire team was from start to finish. The quality of the work and the level of service were both excellent. I would recommend JB West to anyone looking for a reliable and professional roofing company."

Chris T on October 2025

Voted "Best Contractor" by readers of the LaPorte Herald-Argus in 2013 and 2015, Angie's List 2017, and South Bend Tribune Reader's Choice winner, we are honored to continue serving our local communities. We proudly hold the only Owens Corning Platinum Preferred and James Hardie Elite status in Northern Indiana and Southwest Michigan. If you need roofing, siding, gutters or windows, JB West is the exterior remodeling contractor for you! Our company started in 2007 when two brothers started doing roofing and construction jobs and built a reputation for quality and service. A majority of our work comes from happy customer referrals and we have an appreciation program to thank them for their support. We proudly serve LaPorte, Marshall, Porter, St. Joseph and Starke counties in Northwest Indiana and Berrien, Cass Van Buren and Saint Joseph counties in Southwest Michigan. Call 219-363-6151 today for your free estimate!

"I recently had a new roof installed by JB West and was thoroughly impressed with the entire experience. George and Brian were especially helpful throughout the process, providing insurance information and references before I even had to ask. Their communication made everything smooth and stress-free. The install crew was professional, efficient, and completed the job quickly with excellent workmanship. I appreciated the no-pressure approach and how responsive the entire team was from start to finish. The quality of the work and the level of service were both excellent. I would recommend JB West to anyone looking for a reliable and professional roofing company."

Chris T on October 2025

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Roofing questions, answered by experts

The terms “roof sealant” and “roof coating” are used interchangeably to describe the rubber, silicone, polyurethane, or acrylic product applied to the roof’s surface for waterproofing and UV protection. Products like roof caulk can also be called “roof sealant,” but the term is more commonly used for the protective coating.

Good news—asphalt shingles, including architectural shingles, are easily recycled. Talk to your roofing contractor to find out if recycling options are available in your area.

If recycling isn't available, your roofing contractor may recommend renting a dumpster, if your project is on the large side, or collecting the shingles in contractor bags to throw them away. Another option may be to donate new or gently used shingles to a local nonprofit.

You can think of a flat roof as a green roof, as it does offer some environmentally-friendly advantages. When considering an eco-friendly flat roof, some of the green roof pros and cons include that you could place a garden with plants on the flat roof. Manufacturers may use recycled materials in the construction of the flat roof for an eco-friendly design.

Whether or not the terms of your roofing estimate are negotiable depends on the contractor. Some professional roofers will be willing to budge on labor fees to some extent, while others will simply walk away from the potential work rather than lower their fees. In most cases, it’s best not to negotiate the terms, as lower labor charges could lead to your contractor cutting corners. Material costs aren’t negotiable, but you could purchase them yourself to try to save on delivery fees and markups.

You can damage your shingles if you use the wrong type of paint on them. You should always use acrylic latex paint specifically formulated for shingles. Other types of paint may trap moisture, which can cause bigger problems like rot and mildew. Considering that roof replacement costs $9,100 on average, it’s definitely best to avoid making this mistake.

Besides using the right paint, remember that painting your shingles will require increased maintenance.

The Crestwood, IL homeowners’ guide to roofing services

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

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