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50+ Years
experience
Emergency
services
Trusted HVAC & Roofing Services in Lake Bluff, IL
Established in 1952, L.R. Gregory & Son has built a legacy of excellence in HVAC and roofing services across Chicago's North Shore. Our family-owned business combines decades of hands-on experience with a commitment to personalized service, ensuring every project meets the highest standards of quality and reliability. Fully licensed and insured, we offer 24/7 emergency response and guarantee 100% satisfaction on all work performed.

Our technicians specialize in heating, cooling, and roofing solutions tailored to residential and commercial needs, backed by a reputation earned through nearly 70 years of dedicated service to communities like Lake Bluff, Highland Park, and Evanston.
Services
Heating Installation Air Conditioners Installation Roofing Services Roof Repair Chimney Repairs Gutter Services HVAC Maintenance Furnace Installations Heat Pumps Ductless Split Systems
Details
  • Year established: 1952
Highlights and features
  • Family-owned for over 68 years with generational expertise
  • 24/7 emergency service available year-round
  • Fully licensed and insured technicians
  • 100% satisfaction guarantee on all work
  • Serving Chicagos North Shore communities since 1952
What people say
Great family business Thorough and efficient Honest and trustworthy Best pricing found Monitored situation remotely
Services
HVAC Installation
We specialize in complete HVAC system installation for residential and commercial properties. Our experts assess your space to recommend energy-efficient furnaces, heat pumps, or ductless systems tailored to your needs. Backed by decades of experience, we ensure precise installation that maximizes comfort and longevity while adhering to strict safety standards.
Roofing Services
Our full-service roofing solutions include inspections, repairs, and replacements for residential and commercial buildings. From emergency leak fixes to new construction projects, we use premium materials and proven techniques to extend roof lifespan. Our team handles shingles, flashing, gutters, and chimney integration with meticulous attention to detail.
Emergency Repairs
We provide rapid response for urgent HVAC and roofing issues outside regular hours. Our technicians carry essential tools and parts to resolve heating failures, roof leaks, or AC breakdowns efficiently. This service ensures minimal disruption to your comfort or business operations during critical situations.
Gutter Maintenance
Proper gutter function protects your property from water damage. We offer comprehensive cleaning, repair, and installation services to maintain optimal drainage. Our team addresses clogs, leaks, and improper grading while reinforcing connections to downspouts and splash blocks for long-term performance.
Chimney Repairs
We restore chimney functionality and safety through expert masonry repairs. Services include crown sealing, flue liner replacement, and flashing repair to prevent water intrusion. Our technicians also address animal intrusion issues and reinforce structural integrity to meet local building codes and safety standards.
People
Jim Gregory
Owner
Third-generation HVAC and roofing expert with over 40 years of hands-on experience. Jim leads daily operations while maintaining direct client relationships, ensuring every project reflects the family's commitment to quality and integrity since 1952.
Questions
What HVAC services do you offer?
We provide complete HVAC solutions including installation, maintenance, and repair for furnaces, air conditioners, heat pumps, and ductless systems in residential and commercial properties.
Do you handle emergency repairs?
Yes, we offer 24/7 emergency service for urgent HVAC or roofing issues. Our technicians respond promptly to critical situations like heating failures or roof leaks.
Are you licensed for roofing work?
We hold active roofing license #104004375 and maintain full insurance coverage for all services performed across Chicago's North Shore communities.
What areas do you serve?
We serve Lake Bluff, Lake Forest, Highland Park, Evanston, and surrounding Chicago North Shore communities for both residential and commercial projects.
Can you help with chimney issues?
Yes, our services include chimney inspections, crown sealing, flashing repair, and animal intrusion prevention to maintain structural integrity and safety.
Do you offer free inspections?
We provide complimentary roof, gutter, and chimney inspections to assess condition and recommend necessary maintenance or repairs before seasonal weather changes.