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TRUSTED BY CRESTWOOD, IL HOMEOWNERS

  • Average homeowner rating star icon4.5
    Average homeowner rating
  • Verified reviews icon579
    Verified roofing services reviews

Top-Rated Roofers in Crestwood - Updated Nov 2026

Avatar for Bob the Builder Inc
Bob the Builder Inc
4.7(
169
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For BusinessAsphalt Shingle Roofing - Repair+8 more

Serving Crestwood, IL and surrounding areas

Approved

In business since 1973

Free estimates

Customers say: Quick response

"I had storm damage on my roof that had caused my ceiling to collapse in places. After reviewing different companies I chose three and filled out online submissions for quotes. Within an hour Tom had contacted me and gathered all the general information. The other two companies never responded at all. The next day Wes showed up and inspected our roof and ceilings. He took photographs and covered everything with me. The next day Tom sent me some of the photos saying it looked like a great opportunity for homeowners insurance to cover some of the damage. I had not even considered that. Tom walked me through the insurance claim and also dealing with the insurance company which was not always easy. In the end insurance covered practically everything. The work was flawless by the crews who worked on my house. New roof, new vinyl siding with fascia and trim. New gutters. My house completely transformed. Bob the Builder is Amazing!"
Additional Photos
Additional Photos
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Additional Photos

+20

Response time2 days
Response rate100%
8 neighbors recently requested a quote
Avatar for J & B West Roofing & Construction
J & B West Roofing & Construction
4.4(
113
)
Asphalt Shingle Roofing - Install or Replace

Serving Crestwood, IL and surrounding areas

Approved (Corporate)

In business since 2007

Free estimates

Emergency services offered

"I just had a residential roof replacement and I'm very pleased. Gavin was the foreman and did a great job answering all my questions and going the extra mile. I would recommend you talk with this company. They did a great job on my roof. If you hirer them I hope you get to work with Gavin. Art from Benton Harbor, Michigan"
C
C
D
D
B

+19

Response time1 day
Recommended by90%of homeowners
Avatar for Kross Town Roofing & Siding, LLC
Kross Town Roofing & Siding, LLC
4.9(
84
)
Asphalt Shingle Roofing - RepairAsphalt Shingle Roofing - Repair - For Business

Serving Crestwood, IL and surrounding areas

Approved

Super Service Award Winner

In business since 2010

Free estimates

Warranties offered

"Where everyone was trying to get me to replace my roof Chris came out and looked at my roof found a problem and was able to repair it. He is really kind and polite and tries to find the best solution, easy to work with and not a pushy salesman. He stands behind his work. On the day he came out, he came early to beat the rain that was coming that day. This is how contractors should be."
Response time1 day
Recommended by89%of homeowners
Avatar for Montes Roofing, LLC
Montes Roofing, LLC
4.5(
109
)
Flat, Foam or Single Ply Roofing - RepairSealant for Roof - ApplyMetal Roofing - Repair+9 more

Serving Crestwood, IL and surrounding areas

Approved

In business since 1970

Free estimates

Emergency services offered

"I highly recommend Montes Roofing LLC, who did an excellent job replacing my roof. I worked directly with Robert, who was very professional and personable. The pricing was reasonable and the work was completed expeditiously. Nicole Stewart"
Roofing
Roofing
Roofing
Roofing
Roofing

+148

Response time2 days
232 neighbors recently requested a quote
Recommended by91%of homeowners
Avatar for Home Genius Exteriors
Home Genius Exteriors
4.7(
265
)
Asphalt Shingle Roofing - RepairInspection - RoofingRoof - Clean+1 more

Serving Crestwood, IL and surrounding areas

Approved

In business since 2004

Free estimates

Emergency services offered

"While removing the old roof, the aluminum coverings on our mansard roof dormers were damaged. The roofing crew attempted to repair the damage but the result was not satisfactory. As compensation they deducted a small amount from the total bill."
Windows
Windows
Windows
Windows
Windows

+58

Recommended by87%of homeowners
Avatar for Illinois Roofing Inspections
Illinois Roofing Inspections
4.7(
42
)
Inspection - Roofing

Serving Crestwood, IL and surrounding areas

Approved

In business since 1974

Credit card accepted

Offers commercial services

"Philip and his team are great. I've had roof troubles since this roof was put on, and first of all he fixed them. He also gave me a promise for 3 years worry free. There's been an issue and he has immediately remedied. I feel like I paid for the peace of mind and it is worth it. Loyola roofing honored its word with no questions asked, not much more you can ask for."
Response time1 day
Response rate100%
Recommended by97%of homeowners
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Roofing FAQs, answered by experts

A roof replacement can take anywhere from one to 14 days. For most homes, a full replacement that includes tearing off old materials takes about one to two days, though the average project can last up to 12 days. The exact timeline depends on several factors, including the roof's size and complexity, the type of roofing material, the crew size, and weather conditions. Certain materials take longer to install; for example, metal roofs can take seven to 14 days because the material is more difficult to work with than asphalt shingles, wood, or tile. A re-roofing project, where new shingles are installed over old ones, can take half the time or less. It's also important to factor in the time needed to obtain necessary permits. A professional roofing contractor will typically complete the job faster than a DIY approach.

How long shingles last depends on the type of shingles you have on your roof. Asphalt shingles normally last anywhere from 15 to 30 years, metal shingles can last anywhere from 15 to 100 years, and tile shingles can last anywhere from 50 to 100 years or more.

When installed and maintained properly, a cedar shake roof should last up to 60 years. Severe weather and high winds will damage your roof, reducing its life span. Expect a shorter life span if the roofer didn't use top-grade material, didn’t have cedar shake expertise, didn’t create the proper ventilation, or didn’t use the correct fasteners. Keeping up with maintenance will help it last longer. It’s also a good idea to get roof inspections on a regular basis to help spot repairs before they become major issues.

Sometimes chimney caps blow off during storms or fall off after rusting away. While this typically won’t cause structural damage, failing to replace a chimney cap can. A chimney cap prevents moisture, animals, and debris from entering your chimney, all of which can cause serious problems, such as damage to the masonry or blockages in the flue.

If your home doesn't have gutters, you can still hang Christmas lights on the roof using specialized clips. Use roof clips designed to attach to shingles or fascia. For tile roofs or the edges of the rooftop, consider using parrot clips. Adhesive light-hanging clips are also a great option. It's important to avoid using nails or staples, as they can damage your roofing material. For unique or complex installations, it's best to consult a professional Christmas light installer to find the safest and most effective solution for your home.

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.