Custom Retractable Awnings for Chicagoland Homes

Sun when you want it, shade when you don't. Motorized and manual retractable awnings designed, installed, and serviced by Chesterfield Awning. Custom-fit for patios, decks, and backyards across Chicagoland and the greater Midwest since 1958.

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Total Control Over Your Outdoor Space

A retractable awning gives you full control over how you use your patio, deck, or backyard. Open it up when the sun is beating down and you want instant shade. Retract it when you want full sun, when the wind picks up, or when you’re closing things down for winter. Sun, shade, and everything in between, all controlled by the flip of a switch or the turn of a hand crank.

At Chesterfield Awning, we design retractable awning solutions with you, from measurement and specification through to installation and long-term service. We work with industry-leading retractable awning manufacturers whose products we’ve been installing and standing behind for years. Every retractable awning we install is sized and configured for your specific space, matched to the architecture of your home, and installed by our own team.

Why Homeowners Choose Retractable Awnings

A retractable awning does something no other outdoor product does quite the same way. It gives you complete control over sun and shade on your patio, deck, or outdoor space, moment by moment. Here’s what that flexibility actually delivers.

Sun and Shade Flexibility

Extend for shade, retract for open sky. Adapts to how you actually use your outdoor space.

Real Energy Efficiency

Shading windows and doors before heat reaches the glass keeps rooms cooler and cuts cooling costs.

Protection for Your Outdoor Investment

Shields cushions, decking, and floors from UV and rain when you need it, not when you don't.

Extend Your Outdoor Season

Use your patio comfortably from spring through fall, not just the perfect days.

A Cleaner Look When You're Not Using It

Cassette-style models fully enclose the fabric when not in use.

Manual vs. Motorized Retractable Awnings

The first big decision is how you want to operate the awning. Both options are built to last, and both work well. It comes down to how you want to use it day to day.

Manual Retractable Awnings

Hand-cranked, mechanically simple, and built to last. A great fit for smaller patios, budget-conscious projects, or homeowners who prefer no electrical components. If you’re going to use the awning a few times a season and know you’re the type of person who wouldn’t mind cranking a mechanical mechanism, manual is a solid choice.

Motorized Retractable Awnings

Push-button operation with wall switches or wireless remotes. The most popular choice for homeowners because convenience translates to actual use.

Motorized systems from the industry-leading manufacturers we work with can also be paired with:

Wind sensors that automatically retract the awning when gusts pick up, protecting the awning and the mechanism
Sun sensors that automatically extend the awning during peak heat, keeping your rooms cool without you having to think about it
Smart home integration for control through your phone or through your existing smart home system

Fabric, Color, and Design Options

Once you’ve chosen the operation and cassette style, the fun starts. Retractable awning systems come in hundreds of fabric and color combinations, so your awning becomes a design feature of your home, not just a shade cover.

Over 30 solid color options
Classic and modern striped patterns
Textured weaves and tweeds
Custom-printed patterns if you have something specific in mind
Coordinated framing colors to match your home’s exterior
Solution-dyed acrylic and vinyl-coated fabric options rated for Chicago weather

We bring sample books to every consultation so you can see and feel the fabrics in the light of your own home before you commit.

Looking for a Retractable Awning for Your Business?

Retractable systems work as well over sidewalk cafes, pool decks, and storefronts as they do over a backyard patio. Restaurants stretch their outdoor dining season. Hotels cover lounges. Retail draws foot traffic.

The consultation, installation, and service process is the same as residential. What changes is the scale and the commercial-grade hardware built for daily use.

A Note on Permits and HOAs

Two different approvals may apply to your project: city or municipal permits, and HOA or condo board approval. We handle each differently based on how the process actually works.

City and Municipal Permits. We manage the full permit process for most retractable installations across Chicagoland and the greater Midwest. Applications, follow-up, approval — handled.

HOA and Board Approvals. These are typically the homeowner’s responsibility, but we provide all the drawings, specs, and material documentation your board needs to review. You handle the submission; we handle the questions.

How the Process Works

1. Free In-Home Consultation
We visit your home, take measurements, and walk through how you want to use the space.

2. Custom Design and Specification
We help you choose the system, cassette style, fabric, color, and operation that fits your home and budget.

3. Order and Preparation
Your awning is ordered from our trusted industry partners and prepped at our South Holland facility.

4. Professional Installation
Our own team installs, tests every function, and walks you through operation.

5. Ongoing Service
Cleaning, motor service, adjustments, and seasonal care available for as long as you own it.

Frequently Asked Questions

How wide can a residential retractable awning be?

Widths vary by product line and manufacturer, and modern retractable systems can be built at a range of sizes to suit different spaces. For larger patios or decks, multiple units can be installed side by side for continuous coverage. We recommend a configuration and width based on your specific space during your consultation.

How long does it take to install?

Total project time from consultation to installation typically runs six to nine weeks. Timing depends on the specific system you choose, current vendor lead times, and our team’s production and install workload. If there are any vendor backorder issues, timing may extend slightly. We’ll give you a clear estimated timeline once your order is placed.

Are retractable awnings good for Chicago weather?

Yes, when used correctly. Retractable awnings are designed to be extended when the sun is out or in fair weather, and retracted when heavy wind, storms, or snow move in. Motorized models with wind sensors retract automatically when conditions change, so you’re protected even when you’re not home.

Can a retractable awning stay out in the winter?

Retractable awnings should not be left extended during snow accumulation. Retract the awning before winter weather to protect both the fabric and the mechanism. Full-cassette models keep the retracted fabric fully enclosed and protected through the winter.

How long do retractable awnings last?

With proper care, the mechanical components typically last 15 years or more. Fabric life varies by material, color, and sun exposure but commonly runs 10 to 15 years. Fabric can be replaced or re-covered in a different color as a product update when the time comes, extending the life of your overall system.

Are motorized awnings worth the extra cost?

For most homeowners, yes. Motorized awnings get used more often because they’re easier to operate, which means you get more value out of your investment. They’re also easier on the mechanism over time than repeated hand-cranking.

Do you service retractable awnings you didn't install?

In most cases, yes. We offer motor service, cleaning, adjustment, and seasonal care for retractable awnings throughout Chicagoland and the Midwest, including systems installed by other companies. If you want a fabric replacement in a different color, that’s a product update we can quote.

Can a retractable awning be installed on any home?

Most homes can accommodate a retractable awning, but the installation depends on the exterior wall surface, the structural framing behind it, the width you need, and how the awning will tie into any nearby features. We evaluate all of this during your free consultation.

Do you handle permit approvals?

For city and municipal permits, yes. We manage the entire process from application to approval. For HOA or condominium board approvals, the homeowner typically handles the submission with our support. We provide the product specs, drawings, and documentation your HOA requires.

Ready to Take Control of Your Outdoor Space?

Tell us about your patio, deck, or backyard and how you want to use it. We’ll come to you, walk through your options, and design a retractable awning that fits your home and your life. Free consultations. No obligation.

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.

				Called them today to get a quote to replace my fabric on my motorized awning as the place I bought from years ago went out of business talked to Santiago velasco he is the best got to work on sending someone out asap ❤️
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cadibill
7/09/2026
				I called Chesterfield awnings based on a recommendation from another awning company. I was immediately connected to Santiago Velasco. He was courteous and very helpful. It was so easy to talk to him and he quickly arranged for a salesman close to my area to contact me. I am trying to replace or rehung my current awning so I have spoken to quite a few companies and not all my experiences have been good. So it was a breath of fresh air speaking with Santiago. I hope I have the same experience with the salesman.
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Regina W.
7/08/2026
				I am so happy to update this review and share my success story. Chesterfield worked with us and delivered the awning of our dreams. Special Thanks to Juan, Matt, and the team for helping us through some miscommunications and we look forward to working with you again very soon. Couldn’t be happier with how it turned out!
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Chris H.
10/13/2025
				Chesterfield Awning is a great company! For example, today, two technicians, Nick and Hugo, came to my home to remove an existing awning in anticipation of installing a new one. Not only were they skilled and knowledgeable, but also very willing to answer any questions that I had, in a kindly manner. All of this work was arranged by their supervisor, Santiago, who is a great gentleman most willing to please the customer. As the customer, this is so important to me, because nowadays this is not always the case when you deal with different companies. Many Thanks to Chesterfield Awning!!!!!
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April R.
1/29/2025
				My roll-down awning is amazing! I am having trouble with the structure it is tethered to. Santiago was a great help in guiding me to get additional parts needed to solve the immediate problem.
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Sue B.
9/17/2024
				Great quality. Great experience from start to finish. Most importantly, excellent customer service. Ordered a replacement custom awning for our dad’s home. He has been using Chesterfield Awning since 2005. Our consultant Ed did an amazing job. Great customer service from our initial meeting through installation. You won’t be disappointed. Would highly recommend as the new custom awning turned out perfect.
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Jo Z.
9/11/2024
				Had the most pleasant experience with Santiago this morning. He was very friendly and assisted and making an appointment for someone to come out and give me a free estimate. I sincerely hope that whoever comes out for the estimate is as courteous and kind and forthcoming as Santiago.
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S W.
7/22/2024
				Jose is an expert and such and such a pleasure to work with. He knows his business!! Thank you Jose!!!
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Mary B.
7/26/2022
				Chesterfield Awning just beautiful & wonderful work! I’ve had them at my house for 25 years. Thank you Jose & Diego!!The Doyle’s
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Meredith D.
7/21/2022
				My husband and I would like to share our great experience with Chesterfield Awning. It was a smooth and positive experience from start to finish!! It was received in the time frame that we were told by, Ed, the sales consultant and then to the finished product. The installation was done by, Jose’, very remarkable young man who was very professional, cordial, well mannered and We just can’t praise this young man enough for his ability to interact with us elderly folks!!!! The quality of the motorized awning is great and very attractive!! What we are saying is…..Job Well Done my friends!!!!
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Debbie R.
7/14/2022
				Chesterfield Awning is a top notch awesome company. We had a Sunesta rollout shade installed over our patio a few weeks ago. We are so happy with our purchase from Chesterfield. Everything was perfect from the ordering all the way down to the installation. Ed, our sales consultant, was wonderful. He was friendly, professional, knowledgeable, and a pleasure to work with. The installers are top notch; professional, clean, friendly, and conscientious. The office staff is friendly and a pleasure to deal with. We are so happy we chose Chesterfield Awning, and this is a clear testimonial for Chesterfield being in business for so long. Great company and reasonable prices.
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N
6/28/2022
				To the Chesterfield Awning Company, I am extremely grateful and very pleased with the results of my professionally installed awnings. They gave much class and rich style to my home. The awnings brought out my block neighbors as they viewed and complimented the results of the awning. The installer was very nice and professional mannered with with his work ethics and cleans up professionally behind himself. I came outside to see the finished results and was in tears of seeing the beautiful results. Thank you Chesterfield Awning for creating my vision and making my vision come to life.
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Chancery H.
6/20/2022

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.