Chicago Roofing and Gutters

Roofing

4.5(20 reviews)

Chicago, IL·Chicago

Open·6AM-11PM

Request a Consultation Call (708) 815-7028

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About

Rated 4.5★ across 20 reviews, Chicago Roofing and Gutters is a roofing contractor serving the greater Chicago area. Focused on siding and gutters. One reviewer writes: "We were referred to A1 Olson roofing by a coworker/friend and we are very happy with our outcome so far." The end results get strong praise — clients say the work looks professional. Reviewers credit Kevin with strong communication — fast replies and no surprises. They consistently leave the job site clean — a standout detail in testimonials. Affordable rates with solid execution — per client feedback. Knows how to navigate renovations in Chicago's older residential stock. Clients praise honest, detailed quotes that hold through the project.

Project Pricing Insight

Price range:Mid-Range$$

Roofing projects typically cost $5K – $25K in Chicagoland

Hired Chicago Roofing and Gutters? Share what you paid

Amanda Huerta

4 reviews

Highlights

Excellent communicationHigh-quality workmanshipProfessional and trustworthyClean and respectful of propertyTransparent pricing

Specialties

Roof replacement
Siding and gutters
Historic home specialist

Service Areas

Chicago

What Clients Are Saying

Clients liked

“They gave us the best quote, and came out to inspect the roof twice before actually beginning work.”
“Our roof on our bungalow and garage were in very bad shape.”
“They installed a new roof on my house & garage. The price was reasonable.”

Some noted

“Ever since then they have had nothing but problems. All seemed good until the first real rain after installation.”

Read all 20+ reviews on Google

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What 20+ clients say about Chicago Roofing and Gutters

We were referred to A1 Olson roofing by a coworker/friend and we are very happy with our outcome so far. They gave us the best quote, and came out to inspect the roof twice before actually beginning work. We were told that the work would be completed in one day, but some of the crew had emergency repairs to go to the day of the job so our garage was completed one day, and then our house with the full crew was started/completed on the weekend, Kevin communicated this to us immediately so we didn't have an issue with it. Crew cleaned up and took all debris with them, so we didn't have to do anything else once the roof was completed. A great experience thus far!

“Great experience with A1 Olson Roofing.”

Great experience with A1 Olson Roofing! Our roof on our bungalow and garage were in very bad shape. I received an estimate from Kevin Olson on a Tuesday, signed the contract on a Friday, and work began on our roof the very next day on that Saturday. The entire job was completed by Monday. The roofs both look great, the price was reasonable compared to other estimates I had received, the job was completed quickly, and my property was left clean. Thank you! I highly recommend.

Kaylee Curran

May 2024

“Kevin came early in the morning, assessed the repair my roof needed and was able to complete the...”

Kevin came early in the morning, assessed the repair my roof needed and was able to complete the repair quickly and at a very reasonable cost. Angie's List highly recommended them, which gave me peace of mind in hiring his company. We're due for heavy storms today and I am finally not dreading it!

Sky Cotton

May 2024

“I called Kevin Olson on the advice of a friend after a shingle fell off of our roof.”

I called Kevin Olson on the advice of a friend after a shingle fell off of our roof. He called me back the same day and came out shortly after to take a look. Not every company is so accommodating about small jobs so we appreciated his promptness. He provided us an affordable solution, communicated well, and came back in less than a week to do the job. We would definitely recommend him and his company.

Stephanie Springsteen

May 2022

“A1 Olson Roofing installed a new roof on my garage in 2020.”

A1 Olson Roofing installed a new roof on my garage in 2020. Two years later I called the owner Kevin Olson to install a new roof on my house. The installation was very well done and everything was cleaned up when they finished.

Chris Strutz

May 2022

“5 stars for Kevin Olson & his team.”

5 stars for Kevin Olson & his team. They installed a new roof on my house & garage. The price was reasonable. Kevin & his team are all hard workers and they have good attention to detail (my new roof looks great). Kevin does a good job of answering questions. Kevin & team did a good job of keeping the mess contained while they were working. They also cleaned up the yard at the end of each day & when the job was complete (very much appreciated).

Karen G

Nov 2021

“Very honest and patient team.”

Very honest and patient team. They fixed a roofing leak instead of charging a ton to fully replace shingles that didn't need to be replaced. Very good value and they didn't try to oversell me services I didn't need. Will definitely call them again for any further issues.

Stacy Woods

Apr 2021

“Kevin and his crew repaired our garage roof which was damaged in a recent storm.”

Kevin and his crew repaired our garage roof which was damaged in a recent storm. They also repaired facia, soffit and gutter damage. All work was completed in a timely manner and looks great. I would recommend Kevin to anyone looking for quality repairs.

Mark BPC2019

Nov 2020

“Olson roofing and siding is the best in southeast Michigan.”

Olson roofing and siding is the best in southeast Michigan! As a new homeowner, I wanted to ensure my roof was in tip top shape especially after these recent quarantine storms. Olson had an inspector come to the house so quickly and I was given an in depth description of what services my roof needed. Olson worked with my insurance and was able to give me the best deal possible. The crew was professional, prompt, and did an exceptional job! I recommend Olson roofing to anyone and everyone! Excellent company!

Emily Young

Aug 2020

“A-1 Olson Roofing did an excellent job installing a new roof on my garage.”

A-1 Olson Roofing did an excellent job installing a new roof on my garage. The owner Kevin really takes pride in his company. The workers did a beautiful job and cleaned up very well after they completed the work. I will definitely be calling Kevin Olson back to get some other work that I need done around my house.

Richard Strutz

May 2020