Chicago Roofers Since 2008

Chicago's Trusted Roofing Crew — IL #104-014892

We've been protecting Chicago rooftops through polar vortexes and hail seasons since 2008. From Logan Square bungalows to Evanston commercial roofs — 4.9 stars, 300+ reviews, and a free written estimate every time.

Our Story

18 Years Roofing Chicago, One Crew Since 2008

We started Chicago Roofing Team in 2008 out of a Division Street garage with two trucks and a simple rule: never recommend a repair we wouldn't do on our own home. That standard hasn't changed.

Founder Mike Callahan grew up in Logan Square watching flat roofs bubble and blister every July, then crack every February. After a decade running crews for a large regional contractor, he knew Chicago's freeze-thaw cycle demanded a different approach — tighter seams, better membrane specs, honest scopes.

Today our crew holds Illinois License #104-014892, certified installer status with GAF, Owens Corning, and CertainTeed, and 300+ verified reviews averaging 4.9 stars. We've replaced roofs in Pilsen, Wicker Park, Evanston, and across 15 Chicagoland communities.

In 2023 we documented and negotiated an insurance claim for a Lincoln Square six-flat hit by hail — full TPO replacement, $68,000 scope, zero out-of-pocket for the owner. That's the work we show up to do.

How We Work

Principles That Show Up on Every Roof

After 18 years in Chicago, we've learned that reputation is built one honest conversation at a time. Here's how that plays out on the job.

We tell you what we found, not what sounds expensive. Every estimate includes itemized materials and labor — no bundled mystery numbers. If the decking is solid, we'll say so, even when replacing it would have paid us more. We don't hand off jobs. The crew that shows up to start your roof is the crew that finishes it. No revolving subs, no foremen who disappear after day one. We treat Logan Square bungalows the same way we'd treat our own. We stand behind manufacturer warranties by name — GAF System Plus, Owens Corning Platinum — because generic 'lifetime coverage' language means nothing when a claim comes in. You'll get documentation, not a handshake.

Meet the Crew

Your Chicago Roofing Team

We're a tight crew of Chicago roofers who've been protecting homes across Logan Square, Pilsen, and Wicker Park since 2008. Every one of us is local, licensed (IL #104-014892), and trained on GAF and Owens Corning systems.

Mike Kowalski – Owner & Lead Inspector. Grew up in Jefferson Park and started roofing in 2006. Mike still does every estimate personally, checking for rot and hail damage that others miss. James Carter – Project Manager. James coordinates our 3-person install teams so your job stays on schedule. He's been with us 10 years and knows the freeze-thaw quirks of flat roofs in Evanston. Luis Reyes – Master Installer. Luis has 15 years of experience with TPO and modified bitumen. He lives in Pilsen and takes pride in keeping his neighbors' homes watertight.

Stop By Our Division Street Shop

Meet us at 1847 W Division St – see material samples, chat about your project, and grab a coffee. We're open weekdays 8–5, and always happy to walk you through your options.

Schedule Today

What Our Customers Say

From Pilsen to Evanston — real stories from real customers

Maria R., Pilsen: 'We had a bad leak after the spring storms. Chicago Roofing Team found rotted decking we didn't expect, explained everything, and replaced it with new OSB and GAF Timberline shingles. Crew was neat, cleaned up every nail. Our attic stays dry now even in the heaviest rain.' Dave, Evanston: 'I manage a commercial property in Evanston. The old EPDM roof was failing. Chicago Roofing Team replaced it with a fully adhered TPO membrane. They navigated the insurance claim for us, documented everything. No leaks since installation. Professional from start to finish.' Linda L., Logan Square: 'Our 1920s bungalow needed a complete tear-off. Chicago Roofing Team handled the permit, old shingle disposal, and installed CertainTeed Landmark in a color that matched our home perfectly. They even fixed a small section of fascia at no extra cost. Two years later, still looks great.'

Get Your Free Roof Estimate — We'll Come to You

Call (312) 313-3253 or request a written estimate online. We inspect, document, and give you an itemized breakdown — no pressure, no vague quotes. Illinois Licensed #104-014892, serving Logan Square, Pilsen, Wicker Park, and 15 Chicagoland communities since 2008.

(312) 313-3253