30 Memorable Roofs: A Three-Decade Portfolio of Chicagoland Work
Three decades of roofs across Chicagoland. The cedar shake restoration we still get calls about. The first Lake Forest estate. The hailstorm we worked through. The Polish-speaking family whose grandchildren now hire us. A portfolio across thirty years.
Why portfolio matters more than ratings
Online ratings tell you what a contractor's last 100 customers thought. A portfolio across thirty years tells you what kind of work the contractor actually does, on what kind of homes, and whether the work has held up. We have customers from 1998 whose roofs are still on their houses in 2026. We have property managers who've put us on maintenance contracts since 2008 across multi-building portfolios. The roofs we did in our first decade are now 25-30 years old; the roofs from our second decade are 15-20; the roofs we're installing today will be in service through the 2050s. Any of those projects represent a more honest portrait of the company than any single rating.
The first cedar shake project — Mount Prospect, 1997
One of the early projects that defined the standard we'd hold to was a Mount Prospect cedar shake replacement on a home where the homeowner had been told by two other contractors that cedar wasn't worth restoring and should be replaced with asphalt. We disagreed. The cedar inventory was sound; the failure was at the flashing layer. We did the restoration work — copper flashing, selective shake replacement, ventilation correction — for less than a third of what an asphalt replacement would have cost. That roof is still in service in 2026. The homeowner referred us to four neighbors over the following decade. Cedar shake restoration has been part of our work since this project; the diagnostic discipline that separates cedar failure from flashing failure has been the foundation of our cedar practice ever since.
First Lake Forest estate project — 2003
Our first project under Lake Forest Historic Preservation Commission jurisdiction taught us how the architectural-review process actually works. The home was a 1920s Tudor Revival with original slate, original copper flashing, and a Lake Forest Historic Preservation Commission application requirement before any visible exterior work could begin. The homeowner had been quoted full slate replacement by another contractor who hadn't accounted for Commission review. We assessed the project, identified that the slate was largely sound, scoped a copper flashing restoration with selective slate replacement, prepared the Commission application package, walked the homeowner through the review process, and completed the project on time. We've prepared Lake Forest Historic Preservation Commission applications dozens of times since. Architectural review is part of every estate project where it's required.
The 2008 hailstorm — over a hundred homes in two months
The April 2008 hailstorm that hit the northwest suburbs and the North Shore was the largest insurance event in our company's history. We worked through that summer documenting damage on over a hundred properties, meeting adjusters, working directly with carriers, and replacing roofs across the affected zone. The discipline we developed during that summer — written documentation, photo evidence prepared for adjuster review, proper insurance-claim filing, no overpromising on what carriers would or wouldn't cover — became the storm-response process we still use today. The 2025 hailstorm was handled with the same playbook.
Largest commercial maintenance portfolio — 22 buildings, 12 years
Our longest-running commercial maintenance relationship covers a property management firm with 22 buildings across the Mount Prospect / Elk Grove / Arlington Heights corridor. We started with three buildings in 2014 and the portfolio grew as the property management firm acquired additional properties. Every roof in the portfolio has a current condition rating, an estimated remaining service life, and a recommended action with timing. We do semi-annual roof walks on every building, written condition reports go to the property manager and to the building owners, and replacement projects across the portfolio are distributed across budget years rather than concentrated. Commercial roof maintenance as a structured program has become a meaningful share of our commercial work.
Kenilworth slate restoration with full copper rebuild — 2018
A 1910s Kenilworth Colonial Revival with original Welsh slate, original soldered copper flashing, and water entry at multiple chimney details. The slate inventory was sound — most of the original slates had decades of life left — but the copper flashing had reached end-of-life and needed full restoration. The project: removal of slate around every flashing detail, complete rebuild of all chimney counter flashing in 16-ounce copper with new soldered joints, valley copper replacement, step flashing rebuild at every wall transition, and reinstallation of the original slate inventory. Twelve weeks of careful work. The home's architectural character preserved completely, with another half-century of expected service from the slate. Copper flashing on slate roofs is what we specialize in.
First Polish-language project — 1996
Our first commercial project came through a Polish-speaking property owner who was referred to us specifically because we spoke Polish. The homeowner had received estimates from three other contractors but felt more comfortable working with a contractor who could communicate in his first language. We did the project in 1996, did follow-up maintenance work for him over the next twenty years, and his adult children are now homeowners we've worked with on their own roofs. The Polish-speaking community in Chicagoland has been part of how this company grew since the very beginning, and Mówimy po polsku has been on every estimate, every contract, and every job site for thirty years.
Largest single-project — 2022
Our largest single-project undertaking was a multi-building commercial maintenance and replacement program for a manufacturer in the Elk Grove Industrial Park. Three buildings, total roof area approaching 200,000 square feet, mixed system specifications (TPO, modified bitumen, EPDM coverage), phased over an 18-month timeline coordinated with the manufacturer's production schedule so no operations were interrupted. Custom drainage corrections on two of the buildings using tapered insulation. New equipment curbs and parapet flashings on every roof. Documentation and warranty registration for the full scope. The project taught us scheduling discipline and contractor coordination at a scale we hadn't worked at before.
First Glencoe synthetic slate retrofit — 2019
A Glencoe estate home with an aging asphalt roof, originally specified for natural slate but never built that way (the framing couldn't support the load). The homeowner wanted slate aesthetic but didn't want to undertake structural reinforcement. DaVinci Roofscapes Multi-Width Slate was the answer — Class A fire rating, 50-year warranty, slate aesthetic at roughly 25% of natural slate weight, available in colors that matched the surrounding neighborhood's slate inventory. The project paired the synthetic slate with copper flashing throughout. The result was an estate roof that read as natural slate from the street while staying within the structural envelope of the existing framing. We've done dozens of similar synthetic slate projects across Glencoe and the surrounding North Shore communities since.
Three decades, one address, same standard
Thirty years of Chicagoland roofs. Mount Prospect single-family homes from the late 1990s. North Shore estates from the 2000s onward. Multi-building commercial corridors from 2008 forward. Cedar shake restoration. Natural slate. Synthetic slate. Copper flashing. Architectural shingles. Designer asphalt. Modified bitumen. TPO. EPDM. Every project completed under Illinois Roofing Unlimited License #104.010248 from the same Mount Prospect address that opened in May of 1996. Read the full anniversary story on our 30 years page, or call (847) 312-2727 to schedule an assessment for your own home or building. Leaders Roofing Corp, founded 1996 by Jan Koszyk, family-owned since day one.