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Custom Pergolas to Elevate Chicagoland Backyards

Aluminum, louvered, and fabric-covered pergolas designed, built, installed, and serviced by Chesterfield Awning. Custom-built for homes across Chicagoland and the greater Midwest since 1958.

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Design Options

The Outdoor Space You've Been Picturing

A pergola is more than a shade structure. It’s the piece that turns your yard from a place you walk through into a place you actually live. The dinner spot when the weather’s beautiful. The morning coffee ritual under a canopy that filters the light just right. Every pergola we build is designed around your yard, your architecture, and how you actually want to use the space, sourced from our trusted pergola partners or custom-built in our own shop, and installed by our own team.

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Why Homeowners Are Investing in Pergolas

Real Outdoor Living Space

A pergola makes your outdoor space feel like a room: weeknight dinners from May through October, Saturday coffee in the shade, birthday parties and quiet Sunday afternoons. It's the reason life happens outside instead of in front of the TV.

Shade or Sun Where You Want It

Open-frame pergolas give dappled, natural shade. Add fabric panels, a retractable canopy, or a louvered roof for full control over the sun, adjustable by season, by day, or by hour.

An Aesthetic Upgrade

Outdoor living spaces add real appeal for future buyers. The right cover not only protects the furniture, grill, and outdoor kitchen you've already invested in, but also adds a visual upgrade.

Materials, Finishes, and Design Options

Once you’ve chosen a pergola type, the design decisions start. Options include:

  • Aluminum and combination material framing
  • Powder-coated finishes in standard colors or custom color matching
  • Wood-look finishes for a warmer aesthetic without the maintenance
  • Straight, tapered, and architectural column profiles
  • Open beam, louvered, fabric-covered, and retractable canopy roofs
  • Fabric selection in dozens of colors and patterns for soft covers

 

We bring samples and finish books to every consultation so you can see the materials against your home before you commit.

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Types of Pergolas We Build

Aluminum Pergolas

Custom aluminum frames built for decades of Chicago weather without warping, rotting, or fading. A clean architectural look with virtually no upkeep, in a range of powder-coated finishes.

Louvered Pergolas

The premium option. Roof slats open for full sun, close against rain and heat, or tilt to filter the light exactly how you want, with motorized operation from a remote or app. A fully adjustable outdoor room.

Fabric Pergolas

The architecture of an open pergola with the weather protection of a full cover. Panels can be retractable, sliding, or fixed depending on the flexibility you want.

Custom Pergolas

If your vision doesn't fit a standard category, we build custom: custom spans, finish work, and structural anchoring for hot tubs or hanging elements, matched to your home's architecture.

Looking for a Pergola for Your Business?

Pergolas are one of our fastest-growing commercial products too. Restaurants use them to expand outdoor dining, hotels use them over pool decks and courtyards, and hospitality properties use them as design centerpieces of amenity spaces. Same engineering, same design work, scaled for commercial. If you can dream it, we can build it.

See Commercial Products →

How the Process Works

  • Free In-Home Consultation. We visit your home, walk your yard, take measurements, and talk through your goals, style preferences, and budget.
  • Custom Design. Your pergola is designed from scratch, matched to your home’s architecture and intended use. Finish, roof style, and structural features get chosen here.
  • Permitting and HOA Coordination. We manage the municipal permit process directly and prepare everything your review board needs.
  • Fabrication and Preparation. Fabricated in our facility or, for premium partner systems, prepped for install once we receive the shipment. Structural components are quality-checked before installation.
  • Professional Installation. Our own team installs the pergola, tests any motorized components, and walks you through operation and care.
  • Ongoing Service. Cleaning, repair, refinishing, motor service, and adjustments over the years, handled by the same team that installed it. Fabric replacement in a new color is handled as a product update, quoted separately.
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Frequently Asked Questions

How much space do I need for a pergola?
Pergolas range from small intimate structures around 10 feet by 10 feet up to large architectural spans of 20 feet by 20 feet or more. The right size depends on how you want to use the space, what your yard can accommodate, and any HOA or setback requirements. We’ll help you figure out the ideal footprint during your consultation.
In most cases, yes. Municipalities across Chicagoland and the Midwest require permits for permanent outdoor structures, especially attached structures. For municipal permits, we manage the entire process. HOA approval is often separately required, and for those we prepare the documentation your board needs and support you through the submission.
A pergola is typically an open-frame structure that defines an outdoor space and provides partial shade. A patio cover typically has a solid roof and provides full weather protection. A canopy is usually a fabric or metal cover that shelters a specific area. Some pergolas can be built with covered roofs or retractable canopies, blending features across categories. We’ll help you decide which is right for your space.
Total project time from consultation to installation typically runs six to twelve weeks depending on the material, style, custom features, and any permitting or HOA approvals required. Custom or larger projects can take longer. We provide a clear timeline during your design phase.
In many cases, yes. Attached pergolas tie into your home’s exterior wall and can provide a covered extension of your patio right at your back door. We evaluate your home’s structure and the attachment feasibility during the design phase.
Aluminum pergolas commonly last 30 years or more with minimal maintenance. Fabric covers on pergolas typically run 10 to 15 years before replacement, but the frame stays in place and can be reused. Louvered systems have mechanical components that typically last 15 years or more with regular maintenance.
For most homeowners who want maximum flexibility and premium aesthetics, yes. Louvered pergolas give you full control over sun, shade, and rain protection year-round, which means you get more use out of the space. They’re also visually distinctive and add real value to your home.
The pergola can be designed to accommodate lighting, fans, heaters, or other electrical features you’d like to add. Because we don’t do electrical work ourselves, the actual wiring and installation would be handled by your electrician. We plan the structure to accommodate these additions during the design phase so the layout is clean when your electrician comes in.
In most cases, yes. We offer cleaning, repair, refinishing, and mechanical service for pergolas throughout Chicagoland and the Midwest, including ones installed by other companies. Fabric replacement due to age or wear is part of our service work. If you want a fabric replacement in a different color, that’s a product update we can quote separately.
Yes, though how you use it changes by season. Fully covered or louvered pergolas can be used comfortably in more weather. Open-frame pergolas are typically most useful from spring through fall. Adding heaters and fans (installed by your electrician) can extend the usable season on both ends.

Ready to Design the Backyard You've Been Picturing?

Tell us about your yard and how you want to use it. We’ll come to you, walk through your options, and design a pergola that becomes the centerpiece of your outdoor space.

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Trusted Across Chicagoland Since 1958

From the homeowners who’ve counted on us for generations to the businesses whose storefronts we’ve helped build, our customers keep coming back.

The Chesterfield Maintenance Program

The Maintenance Program bundles cleaning, seasonal storage, priority repair scheduling, and inspections into one relationship. For homeowners protecting an investment and property managers coordinating across sites, it’s the smart way to keep every awning sharp without the coordination burden.

Our Maintenance Program