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Serving All of Chicagoland

Call 773-286-5446
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Classic Chicago brick bungalow with a new charcoal shingle roof

Your Chicagoland Roofing & Home Improvement Experts

For over 50 years

Roofing, windows, siding, gutters & more — quality work from a family-owned business you can trust.

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Free, no-obligation estimate.

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No obligation. Your information is kept private.

Backed by written warranties & 50+ years of local experience.

  • A+ BBB Accredited
  • 50+ Years Experience
  • Licensed & Bonded
  • 4.4 Stars on Google
  • 0% Financing Available
Why Choose Diamond

The Diamond Difference

For more than 50 years, Chicagoland homeowners have trusted Diamond Home Service for honest recommendations and dependable workmanship.

Get a Free Estimate
  • More than 50 years serving Chicagoland
  • Licensed and bonded contractors
  • Written estimates
  • Written warranties
  • Quality products
  • Clear communication
  • 0% financing options
  • Free, no-obligation estimates
0% Financing Available

0% Financing on Your Next Home Project

Qualified homeowners can move forward now and pay over time with 0% financing — making roofing, siding, windows, and gutters more manageable.

  • Simple financing inquiry
  • 0% financing for qualified homeowners
  • Clear next steps
  • No obligation to request information

Financing is subject to credit approval. Available terms and conditions may vary.

What is the diamond difference? Watch now.

Recent Projects

Recent Projects Across Chicagoland

Chicago two-story home with a new dark gray shingle roofChicago

Roof Replacement

Full tear-off and new architectural shingle installation.

New light gray vinyl siding on a suburban homeWest Suburbs

Siding Replacement

Fresh vinyl siding that won't warp, peel, or need painting.

New white double-hung vinyl windows on a brick homeChicago

Window Installation

Energy-efficient replacement windows for lower utility bills.

Suburban ranch home with a new brown shingle roof and matching guttersSouth Suburbs

Roof Replacement & Gutters

New shingle roof paired with seamless gutters.

New white seamless gutters and downspout on a residential roof edgeNorth & NW Suburbs

Seamless Gutters

Custom-formed gutters and downspouts to protect the foundation.

Chicago brick two-flat with a new charcoal shingle roofWest Suburbs

Roof Replacement

Durable charcoal shingles on a classic brick two-flat.

Project photos are representative of Diamond Home Service roofing, siding, window, and gutter work.

Diamond Home Service did an excellent job on our new roof. The team was professional, on time, and cleaned everything up. Highly recommend!
— Michael R., Orland Park, IL
Customer Reviews

Trusted by Chicagoland Homeowners

Verified reviews from Google Reviews.

Well, to begin with Diamond Home Service was very prompt. They were on time each time that they came. They did an excellent job and told us everything step-by-step. They cleaned up the areas they worked in and were very considerate of our property. Overall a great experience — all our questions were addressed.

Michele T.

Roof Replacement · Google Review

They were out within a week with a crew big enough to complete the roof in one day.

Naight P.

Roof Replacement · Google Review

My family has used this company for many years. Interacted with the owner directly for replacing windows today. We have referred many family and friends exclusively to this company. The owner was very professional and compassionate, and the company has been in business for over 50 years. Excellent services as always!

Marissa G.

Windows · Google Review

Service Area

Proudly Serving Chicagoland

From Chicago to the south and west suburbs, we're your local roofing and exterior experts.

  • Evanston
  • Wilmette
  • Kenilworth
  • Winnetka
  • Glencoe
  • Highland Park
  • Highwood
  • Deerfield
  • Northbrook
  • Glenview

And More! Call Today: 773-286-5446

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Local. Reliable. Right Around the Corner.

Wherever you are in the Chicagoland area, we're ready to help.

FAQ

Frequently Asked Questions

A professional inspection is the best way to tell. Localized damage or a relatively new roof often calls for repair, while widespread wear, aging shingles, or repeated leaks may point to replacement. We provide a written recommendation.

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