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TRUSTED BY CRESTWOOD, IL HOMEOWNERS

  • Average homeowner rating star icon4.5
    Average homeowner rating
  • Verified reviews icon573
    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
Additional Photos
Additional Photos
Additional Photos

+20

Response time2 days
Response rate100%
7 neighbors recently requested a quote
Avatar for Guardian Roofing Systems, LLC
Guardian Roofing Systems, LLC
4.9(
70
)
Flat, Foam or Single Ply Roofing - RepairFlat, Foam or Single Ply Roofing - Repair- For Business

Serving Crestwood, IL and surrounding areas

Approved

Super Service Award Winner

In business since 2010

Free estimates

Emergency services offered

"I had a great experience working with Guardian Roofing Systems. From start to finish, they were professional, prompt, and thorough. The team showed up on time and completed the job within the timeframe they promised, which I really appreciated. What stood out most was how clearly they explained every step of the process—from the initial inspection to the final cleanup. They took the time to answer my questions and made sure I understood what work was being done and why. Overall, I’m very satisfied with the quality of their work and the level of service I received. I wouldn’t hesitate to recommend them to anyone in need of flat roofing services."
roof coating
new roof installation
decking
insulation
base sheet

+13

Response time2 days
Response rate91%
79 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 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
250 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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Showing 1-10 of 471
Roofing FAQs, answered by experts

Whether you should choose a flat roof or a sloped roof depends on your particular situation. Flat roofs tend to be less expensive to install. However, sloped roofs have longer lifespans and stand up better to heavy snow and other inclement weather.

Keep in mind that even a flat roof needs to have a slight slope, usually around 1/2 inch for every foot. If it is completely flat, water will pool and cause damage, either from weight or leakage or rot.

Yes, it’s possible to replace drip edge flashing without removing shingles, but it’s not a good idea. You’ll have to lift the bottom shingles up to remove the old drip edge, install the new material, and then lay the lifted roofing material over the new drip edge. Bending roof shingles can cause damage, and if you have ongoing issues with roof leaks that prompt drip edge replacement, it’s a good idea to consider a roof and drip edge replacement to avoid ongoing issues.

Tar and gravel roofs last an average of 30 years, which is longer than the average lifespan of many other flat roofs. The gravel on top of the waterproof membrane helps protect the roof from UV damage and physical damage, so if you keep your roof drains clear and carry out annual roof inspections to catch issues early, you could see up to 40 years of useful life from your roof.

Unfortunately, there’s no definitive answer to this question, but the wind rating of your shingles will give you a good idea of what wind speeds can damage your roof. If you’re concerned about damage, inspect your roof following windy conditions to look for signs of wind damage to your shingles. When in doubt, consider hiring a professional who fixes roofs to carry out an expert inspection. Remember that hurricanes, tropical storms, and tornadoes are likely to cause the most damage, but even severe thunderstorms can bring winds that compromise your roofing system.

Flat roofs are cost-effective, offer usable space, and are easy to maintain. Foam and single-ply materials provide excellent insulation and durability.

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.