Roof Replacement in Chicago
Old shingles, storm damage, or a roof past its lifespan? Pegasus Construction handles full roof replacements on Chicago homes — tear-off, new underlayment, and a quality install. Free estimates. Licensed & insured.
Roof Replacement Built for Chicago Homes
A New Roof That Lasts
Chicago roofs take a beating — freeze-thaw cycles, heavy snow loads, hail, and high winds all accelerate wear. When a roof reaches the end of its life, continued patching only delays the inevitable. Pegasus Construction gives you an honest assessment and a complete replacement done right the first time.
Signs Your Roof Needs Replacement
- Shingles curling, cracking, or missing
- Water stains on ceilings or in the attic
- Roof is 20+ years old
- Granule loss in gutters or downspouts
- Sagging or soft spots on the roof deck
- Energy bills rising with no other cause
Expert Roof Replacement, Root Cause Fixed
Your Roof Replacement, Handled End to End
We inspect, diagnose, and replacement your roof from top to bottom — shingles, flashing, valleys, gutters, and ventilation — so the replacement holds instead of becoming a recurring problem. No subcontractors, no surprises.
Roof Replacement Services for Every Chicago Home
The most common roof replacements we handle on Chicago homes. Built to last through freeze-thaw cycles, hail, and heavy snow.
Asphalt Shingles & Replacement
Curling, cracking, missing, or granule-losing shingles replacemented or replaced with matching architectural shingles. We nail off correctly, re-flash as needed, and leave no exposed decking.
Flashing & Valley Replacement
Failed step, counter, or valley flashing is the most common cause of roof leaks. We remove the old flashing, re-bed it properly, and seal every seam so water can’t get in.
Storm & Hail Damage
Hail impacts, wind-lifted shingles, and storm debris can compromise your roof overnight. We assess the full damage area, document it for insurance if needed, and replacement everything at once.
Roofs Built for Chicago’s Homes
We Know Chicago’s Older Rooflines
Chicago bungalows, greystones, and two-flats often have low-slope sections, multiple valleys, and original flashing from decades ago. We replacement them properly — no replacees over replacees, no shortcuts.
Built for Chicago Weather
We use materials rated for Zone 5 climate — impact-resistant shingles, proper ice-and-water shield at eaves, and flashing that holds through decades of freeze-thaw cycles.
Permits & Chicago Building Code
Most roof replacements don’t require permits, but we advise you upfront on any code requirements. If permits are needed, we handle them with the Chicago Department of Buildings.
Neighborhoods We Serve
From Lincoln Park and Lakeview on the North Side to Beverly and Bridgeport on the South Side — we replacement roofs across Chicago and the surrounding suburbs.e South Side—Pegasus replaces windows across all 77 Chicago neighborhoods and the surrounding suburbs.
Years Serving Chicago
Projects Completed
15 Google Reviews
Licensed, Bonded & Insured
Our Simple Three-Step Plan
Schedule a Free Inspection
Call or fill out our form. We’ll set up a free, no-pressure roof inspection at a time that works for you.
On-Site Assessment & Proposal
We inspect every problem area on-site and walk you through exactly what needs replacement, why it failed, and what it will cost — no surprises, no upselling.
Professional Replacement
Chicago roofs take a beating — freeze-thaw cycles, heavy snow loads, hail, and high winds all accelerate wear. When a roof reaches the end of its life, continued patching only delays the inevitable. Pegasus Construction gives you an honest assessment and a complete replacement done right the first time.
More Ways Pegasus Can Help
Window Installation
New window installs for additions, new construction, or when you need a different opening size.
Roof Replacement
Full roof replacement when replacement isn’t enough. New decking, underlayment, and shingles.
Siding Installation
Protect your home with fiber cement, vinyl, or engineered wood siding built for Chicago weather.
Affordable Roof Replacement, Flexible Payments
Low rates and friendly loan consultants make your project easier on the budget. We offer financing to help you get started sooner.
Servicing Chicago and the Surrounding Suburbs
Chicago Neighborhoods
Surrounding Suburbs
Our team of experienced builders has a solid track record when it comes to creating exceptional spaces. We ensure that the construction process is stress free, with transparent communication on both deadlines and cost estimates – guaranteeing you’ll no un welcome surprise.
Roof Replacement FAQs
When should I replacement vs. replace my roof?
If your roof is under 15–20 years old and the damage is localized — a few shingles, a flashing failure, a single leak area — replacement almost always makes sense. If you have widespread granule loss, multiple leak points, or a roof over 20 years old, we’ll tell you honestly whether replacement is the smarter investment.
How long does a roof replacement last?
A quality replacement done right — properly seated shingles, correctly lapped flashing, proper sealant — can last the remaining life of your roof. Patches that just cover symptoms without fixing the underlying failure won’t. We fix the root cause.
Can a full roof replacement be covered by homeowners insurance?
If your roof was damaged by a covered peril like hail or wind and requires full replacement rather than repair, we document the damage and can work directly with your insurance adjuster to support your claim.
Do I need a permit for a roof replacement in Chicago?
Most like-for-like roof replacements are permit-exempt. If your replacement involves structural decking changes or you’re in a municipality with stricter rules, we’ll advise you upfront and pull any required permits.
How long does a roof replacement take?
Most residential roof replacements are completed in a single day. Larger jobs involving decking replacement or extensive flashing work may take two days. We give you a clear timeline before we start.
Should I replace the flashing when I replace my roof?
Yes — flashing should always be replaced along with the roofing material during a full replacement. Reusing old flashing is a common shortcut that leads to leaks within a few years.
What does roof replacement cost?
Minor replacements (a few shingles, small flashing section) typically run $300–$700. More extensive replacements run higher. We provide a clear, itemized estimate with no surprises.
How do I get started with a roof replacement?
Call 773-377-4898 or request a free estimate online and we’ll schedule your free roof inspection.
Ready to Stop That Leak Before It Gets Worse?
Get a free roof inspection from Pegasus Construction and find out exactly what your roof needs — honest recommendations, no upselling.
