Call Now
Website
Call
Business Details
23 Years
experience
Emergency
services
Expert Roofing & Exterior Services in Chicago
Founded in 2003, Heritage Contractors is a family-owned Chicago-based business specializing in exterior building solutions. With over 20 years of combined experience, we provide roofing, siding, window replacement, and gutter services for residential and commercial clients. Our team prioritizes customer satisfaction, offering transparent consultations, certified product installations, and seamless insurance coordination.

We maintain industry certifications from GAF, CertainTeed, and Raindrop Gutter Guard, ensuring quality workmanship. Our commitment to Chicagoland communities is reflected in our reputation for reliability, honest assessments, and durable solutions tailored to local climate challenges.
Services
Roofing Siding Window Replacement Gutter Services Commercial Roofing
Details
  • Year established: 2003
Highlights and features
  • 20+ years of Chicagoland exterior construction experience
  • Certified installers with GAF, CertainTeed, and Raindrop credentials
  • Transparent process with no-pressure consultations
  • Specialized insurance claim coordination expertise
  • Customer satisfaction rated #1 priority in client testimonials
Associations and certifications
  • GAF
  • CertainTeed
  • Raindrop Gutter Guard
What people say
Excellent workers Timely and punctual Amazing customer service Exceptional work Highly recommend
Services
Roofing
Heritage Contractors provides comprehensive roofing solutions including installations, repairs, and inspections. Our certified technicians use premium materials like GAF shingles to ensure durability against Chicago's weather. We specialize in storm damage restoration and insurance claim processing, offering free inspections to determine whether repairs or full replacements are needed.
Siding
We offer professional siding installation and replacement with vinyl, fiber cement, and LP SmartSide options. Our team helps homeowners choose materials that balance aesthetics, durability, and energy efficiency. Fiber cement options provide wood-like appearance with superior weather resistance, while vinyl offers low-maintenance affordability for Chicago properties.
Window Replacement
Our Marvin window installations improve energy efficiency and home aesthetics. We provide consultations to select appropriate styles and materials that withstand Chicago's climate. The process includes precise measurements, old window removal, and proper sealing to prevent air and water infiltration during installations.
Gutter Services
We specialize in gutter installation, repair, and Raindrop Gutter Guard systems. Our services prevent water damage to foundations and basements by ensuring proper drainage. Certified technicians assess existing systems, recommend upgrades, and install maintenance-free solutions tailored to property needs and local weather patterns.
Commercial Roofing
Heritage Contractors offers commercial roofing solutions including silicone coatings, tear-offs, and maintenance programs. We assess business needs to determine cost-effective options between repairs and replacements. Our team works with property managers to minimize disruptions while ensuring code compliance and long-term protection for commercial properties.
People
John Pienta
Owner
John Pienta leads Heritage Contractors with over 20 years of Chicagoland construction experience. He personally oversees projects, providing expert assessments and ensuring quality standards. His hands-on approach includes detailed consultations, on-site supervision, and post-completion follow-ups to guarantee customer satisfaction.
Abigail S.
Project Coordinator
Abigail manages client communications and project scheduling with 8+ years in exterior construction coordination. She streamlines the process from initial inquiry through completion, ensuring timely execution and clear updates throughout each project phase.
Questions
How long will my new roof last?
Properly installed architectural shingles typically last 20-25 years with regular maintenance.
When should I replace my roof instead of repairing it?
Replacement is recommended when there's widespread damage, persistent leaks, or if your roof is over 20 years old.
Why are gutters important for my home?
Functional gutters prevent foundation damage, basement flooding, and siding erosion by directing water away from your property.
Do you work with insurance companies for storm damage claims?
Yes, we specialize in insurance claim coordination and provide documentation for storm damage repairs.
What siding options do you offer?
We install vinyl, fiber cement (HardiePlank), and LP SmartSide with various styles and durability options.
Videos