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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 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

"Angelo was helpful, thoughtful, and professional during the entire process. He explained everything thoroughly to make sure we knew what we were getting and communicated every step along the way. We wouldn't hesitate to call Guardian Roofing for any future roofing needs."
roof coating
new roof installation
decking
insulation
base sheet

+13

Response time2 days
Response rate91%
88 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

"Drew was my initial contact and inspected for hail damage..told me there was and he was also there on very short notice to meet with my insurance co.. very pleasant gentleman..I never had to call the office for updates as Caprice called often..then came Frank and his crew to install roof...what a hard working crew...they came at 630 and were done at 1230..amazing..thanks to all. very pleasant experiance and a beautiful new roof"
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

"Prompt response to my call about a fallen gutter due to a major ice dam. Within hours, they cleared the walkway & debris for safety. Gutter replacement & other roof repairs were done 3 days later. Excellent & timely communication, follow-up and work. I highly recommend Montes Roofing!"
Roofing
Roofing
Roofing
Roofing
Roofing

+148

Response time2 days
236 neighbors recently requested a quote
Recommended by91%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

"I had an excellent experience working with Illinois Roofing Inspections. The team was incredibly knowledgeable and professional throughout the entire process. They conducted a thorough inspection of my roof and identified several issues that needed to be addressed. Their report was detailed and easy to understand, and they took the time to explain the findings and answer all of my questions. They also provided me with a clear plan of action to address the issues and prevent further damage to my roof. The team was prompt and efficient in completing the repairs, and they did an excellent job. My roof now looks and functions better than ever before. I am extremely satisfied with the services provided by Illinois Roofing Inspections and would highly recommend them to anyone in need of roofing inspections or repairs."
Response time1 day
Response rate100%
Recommended by97%of homeowners
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Roofing FAQs, answered by experts

You can put new shingles over old shingles, but most municipalities only allow for two layers of shingles before you have to rip off the old roof and start fresh. In some areas, only a single layer of shingles is allowed due to the weight a bundle of shingles adds to your structure. In most cases, it’s a good idea to remove your old shingles before you install new shingles, especially if you suspect that a roof leak may have compromised the decking underneath.

Rain shouldn’t come in through your ridge vents unless your vents are damaged or the rain is accompanied by very high winds. Most ridge vents use flashing or baffling to keep out rain, snow, and debris. If your ridge vent isn’t baffled, rain is more likely to enter your attic, so ridge vents with baffles are a better choice in areas with regular rainfall.

Underlayment is required by building code, so any roof installed without it is technically against code. The underlayment acts as the second layer of defense against water, so installing a roof without underlayment means a much higher risk of roof leaks. You’ll have the best chance of avoiding roof leaks if you install drip edge flashing covered by underlayment, and then install your roofing material over that.

Ensures precision fitting, optimizing durability and efficiency against weather elements.

Tile roofing is durable, fire-resistant, and energy-efficient. It also adds aesthetic appeal and, with proper maintenance, can last 50-100 years.

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.