Windy City Gutter Cleaning

Business Details

23 Years

experience

Emergency

services

Expert Gutter Cleaning Services in Chicago

Since 2003, Windy City Gutter Cleaning has been a trusted family-owned business serving Chicagoland. Our licensed and insured team specializes in comprehensive gutter maintenance for residential and commercial properties. We prioritize customer satisfaction through efficient service, transparent communication, and meticulous attention to detail. Our process includes online scheduling, accurate estimates, and timely execution with weather-contingency planning. We serve over 100 neighborhoods across Chicago and surrounding suburbs, adapting to seasonal challenges while maintaining safety standards.

Our team personally handles every job, providing before-and-after documentation and proactive repair notifications. With decades of combined experience, we demonstrate expertise in gutter system optimization and water damage prevention. Our commitment to quality is reflected in our repeat customer base and positive client testimonials. We maintain authoritativeness through consistent service excellence and community engagement. Our trustworthiness is evidenced by our licensing, insurance, and transparent business practices.

Services

Gutter Cleaning Gutter Inspection Downspout Cleaning Gutter Maintenance Emergency Gutter Services

Details

Year established: 2003

Highlights and features

Family-owned business serving Chicagoland since 2003
Fully licensed and insured professional team
Convenient online scheduling with price transparency
Bi-annual cleaning recommendations for optimal protection
Serving over 100 neighborhoods across Chicago and suburbs

What people say

Fast, professional, reasonably priced Prompt, professional, competent Timeliness and quality of work Before and after pics provided

Website

Update Listing

Services

Gutter Cleaning

Our comprehensive gutter cleaning service removes debris, leaves, and blockages from roof gutters and downspouts. Using professional equipment, we ensure proper water flow to protect your property's foundation and exterior. The service includes debris removal, water flow testing, and post-cleaning inspection to maintain optimal gutter function year-round.

Gutter Inspection

Professional gutter inspection identifies potential issues like leaks, sagging, or improper drainage. Our technicians examine gutter alignment, downspout connectivity, and structural integrity during each service visit. We provide immediate feedback and repair recommendations to prevent water damage to roofs, walls, and foundations.

Downspout Cleaning

This specialized service clears blockages in vertical downspouts that channel rainwater away from buildings. Using targeted techniques, we remove compacted debris to restore proper drainage flow. The process prevents water overflow that could damage landscaping, siding, and foundation systems during heavy rainfall events.

Gutter Maintenance

Our maintenance program includes bi-annual gutter cleaning recommendations to prevent seasonal buildup. We offer customized schedules for properties in heavily wooded areas and provide ongoing care to maintain system effectiveness. Services include debris removal, hardware tightening, and minor adjustment recommendations.

Emergency Gutter Services

Available for critical gutter issues requiring immediate attention, our emergency service addresses sudden blockages, storm damage, or overflow situations. We prioritize rapid response while maintaining safety protocols during adverse weather conditions. Service includes urgent debris removal and temporary stabilization measures.

People

Shannon

Owner

Shannon leads Windy City Gutter Cleaning with over 15 years of hands-on experience in gutter maintenance. He personally oversees operations, ensuring quality control and customer satisfaction. His team provides prompt service with transparent communication and detailed work documentation.

Questions

What areas do you service?

We serve Chicago and over 100 surrounding suburbs including Naperville, Evanston, and Schaumburg. Our service area covers both residential and commercial properties across Chicagoland.

How much does gutter cleaning cost?

Pricing varies based on property size and complexity. Request a free estimate through our website to receive a customized quote with no obligation for Chicago and suburban locations.

Do you offer emergency services?

Yes, we provide emergency gutter services for urgent situations. Availability depends on weather conditions, as we prioritize worker safety during extreme weather.

How do payments work?

We accept payments through Chase QuickPay or Zelle. Payment links are sent after service completion, with options for prepayment available upon request.

What's your service process?

Our process includes online scheduling, estimate confirmation, service execution within 1-14 days, and post-service cleanup. We document completed work and provide before/after photos for customer verification.

When should gutters be cleaned?

Experts recommend bi-annual cleaning, typically in spring and fall. We offer year-round service weather permitting, with special attention to pre-winter preparation and post-storm maintenance.

Reviews (6)

Write a Review

Laura L.

Jul 05, 2021 Report

Positive:Professionalism,Punctuality,Quality,Responsiveness,Value
I have used Windy City the last 2 years to clean my gutters. I have been very happy with their service. They always do a great job.
Service:Gutter cleaning

Rosanne Plescia

Jun 27, 2021 Report

Positive:Professionalism,Punctuality,Quality,Responsiveness,Value
We have used Windy City for several years and have always found them to be responsive and on time. We appreciate their professional services and have been very satisfied with their service.
Service:Gutter cleaning

John Chiczewski

Jun 20, 2021 Report

I tried using their service made several calls never got a callback,put in for an estimate I did get an estimate back in a timely manner and an email saying that I would pay online one services were done, I then got an email back four days later saying I did not put my information in they wanted my credit card information my banking information in my routing information prior to doing business with them this seems unacceptable to me. Tried calling them several more times leaving my phone number and my name and never a response. I had to go use a different service.

Marie Tyse

Mar 18, 2021 Report

Positive:Professionalism,Punctuality,Quality,Responsiveness,Value
I have used Windy City Cleaning for a number of years. They provide superior service in a timely manner at very reasonable prices. I am pleased with their work and highly recommend them.
Services:Gutter cleaning,Power/pressure washing

Benjamin Glick

Dec 02, 2020 Report

Positive:Professionalism,Punctuality,Quality,Responsiveness
Windy City has been cleaning our gutters for years. Our Victorian house has a challenging roof, but they always do a great job. They are also responsive and reliableif a freeze prevents a cleaning, they find a time to get here when the weather permits. Excellent service, reasonable prices.
Service:Gutter cleaning

Angela O'Brien

Jun 13, 2019 Report

Never showed up. They stated they would be here within 14 days, and nothing. Contacted the company and they then noted that they would expedite the request, and be here within 4 days, and still no-show. Very disappointing