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Since 2009
Chicago'sOriginal Roof Deck Company
Bringing the interior to the exterior. Full-service design-build for rooftops, terraces, and outdoor living spaces across Chicago.
20+
Years Experience
3,000+
Projects Built
50+
Design Awards
100%
Client Satisfaction
Licensed
Bonded
Insured
A+ BBB Rating
4.9★ Houzz
Who We Are
Chicago's Premier
Roof Deck Company
Since 2009, Chicago Roof Deck & Garden has been transforming rooftops into Chicago's most stunning outdoor living spaces. We're craftsmen who happen to run a business—not the other way around.
From the first sketch to the final walkthrough, one dedicated team handles your entire project. Design, permits, and construction—all under one roof. That's the soup-to-nuts approach that sets us apart.
Licensed, bonded, and insured with in-house architects, engineers, and over 60 skilled tradesmen ready to bring your vision to life.
60+
In-House Tradesmen
500+
Permitted Projects
100%
Permit Approval
Our Work
Featured Projects
commercial
The Urban Play & Chill Deck
Lincoln Park, Chicago
View Project
commercial
Bradley Center
North Center, Chicago
View Project
residential
Serene Shade & Swim
Willow Springs
View Project
residential
Sunset Bar & Lounge
Bucktown, Chicago
View Project
residential
Urban Green Sanctuary
Lake View, Chicago
View Project
residential
Sky Court & Garden Haven
Bucktown, Chicago
View Project
The Transformation
From Forgotten to
Unforgettable
Materiality
Texture & Form
We select only the finest materials—sustainable hardwoods, architectural steel, and porcelain—to ensure beauty that endures.
Sustainable Timber
Ipe Hardwood
Ipe Hardwood
Sustainable Timber
Dense, durable, and naturally resistant to rot. The gold standard for rooftop decking.
Structural Metal
Architectural Steel
Architectural Steel
Structural Metal
Custom-fabricated in our local shop. Provides strength with a sleek, modern profile.
Engineered Surface
Porcelain Tile
Porcelain Tile
Engineered Surface
Non-porous, slip-resistant, and virtually indestructible. Modern elegance that handles Chicago winters without fading or cracking.
Vertical Garden
Living Walls
Living Walls
Vertical Garden
Lush, irrigated vertical planting systems that soften urban edges and improve air quality.
Our Team
Meet the
Team
Designers, builders, and problem-solvers who turn rooftops into your favorite room in the house.
Managing Principal
1 / 14
Darren Flynn
“Darren Flynn is the Managing Principal and founding member of Chicago Roof Deck & Garden, started in 2009. He has over 20 years of experience in residential, commercial and retail construction and shares the overall strategic and operating responsibility.”
View Full ProfileWhat We Do
Full-Service
Design-Build
From first sketch to final walkthrough, our team handles every detail of your outdoor living project.
Custom home and renovation design by licensed architects.
- Licensed Architects
- Custom Design
- Permit-Ready
Interior design services including space planning and finish selection.
- Licensed Architects
- Custom Design
- Permit-Ready
Site planning and property layout design for construction projects.
- Licensed Architects
- Custom Design
- Permit-Ready
Photorealistic 3D renderings to visualize your project before construction.
- Licensed Architects
- Custom Design
- Permit-Ready
Existing condition surveys and as-built documentation services.
- Licensed Architects
- Custom Design
- Permit-Ready
Complete construction document sets for permitting and building.
- Licensed Architects
- Custom Design
- Permit-Ready
Complete building permit filing and coordination with Chicago agencies.
- Licensed Architects
- Custom Design
- Permit-Ready
Zoning code review and compliance analysis for Chicago roof deck and construction projects.
- Licensed Architects
- Chicago Code Expertise
- Variance Strategy
Elements
Curated
Components
Every rooftop tells a story. Our custom-fabricated elements transform ordinary spaces into extraordinary outdoor retreats.
Client Stories
What Our Clients Say
houzz Review
“We committed to a 3 part project inclusive of garage deck, rear patio, and roof top deck. Each space different in anticipated use. CDRG was instrumental in guiding us through the permitting challenges and structural issues we encountered along the way. Likewise, Covid presented resource issues which...”
David G.
Chicago • Full Renovation
Peace of Mind
Licensed, Bonded
& Insured
Full City & State Compliance
100%
Permit Approval
500+
Permitted Projects
3,000+
Projects Completed
Licenses & Certifications
City of Chicago
- ●General Contractor License
- ●Exterior Contractor License
State of Illinois
- ●Roofing License (Unlimited)
- ●Licensed Architect
- ●Licensed Structural Engineer
Insurance & Bonding
- ●Surety Bond
- ●General Liability
- ●Workers Compensation
Associations
- ●BIAGC Member
- ●NAHB Affiliated
How We Work
Our Process
01
Consult
Understanding your vision
02
Design
Crafting the concept
03
Plan
Permits & details
04
Approve
City sign-off
05
Craft
Custom fabrication
06
Build
Expert installation
07
Enjoy
Your new space
Trusted By
Houzz
Best of Houzz 2024Chicago Tribune
FeaturedArchitectural Digest
Top PickBetter Homes & Gardens
Editor's ChoiceHGTV
As Seen On