Why Choose Windy City Gutter Cleaning in Highland Park?
Family-Owned Since 2003
We’ve been taking care of Highland Park homes for over 20 years. We treat every customer like part of our own family and we’re obsessive about doing the job right.
Safety First
We only send trained guys up on roofs. We’re extra careful because we know how dangerous it can be if it’s not done properly.
Keep Your Gutters Working Year-Round
Regular gutter cleaning keeps water flowing the way it should and protects your home from expensive damage down the road.
Services We Offer in Highland Park
Gutter Cleaning
Gutter Repair
Power Washing
Window Cleaning
How Our Process Works
1
Free Estimate
Just fill out the quick form and tell us what’s going on with your gutters. We’ll review it and send you a fair price by email — no charge, no pressure.
2
Booking
If you like the estimate, let us know. We’ll send you a secure link to put your payment info on file. We only charge after the job is done — never before.
3
Scheduling & Service Day
We can usually get to you the next day or within 1–14 days, depending on our schedule in your neighborhood. When we’re in Highland Park, we’ll swing by, get up on the roof, clean and repair everything, haul away all the debris, put it by your trash bin, and leave the place looking clean.
4
After the Job
We’ll email you the details of what we did. A few days later we’ll charge the card or account you have on file.
Ready to get those gutters taken care of? Reach out to our team — we’re here to help.



