Thinking about swapping your windows or updating the façade on your Old Town condo or townhome? If your block sits in a Chicago Landmark district, the rules are different from a typical renovation. It can feel confusing at first, especially when both the City and your HOA have a say.

In this guide, you’ll learn how landmark status works in Old Town, what exterior work triggers review, how window projects are evaluated, and how HOA approvals and City permits fit together. You’ll also get practical timelines, cost considerations, and a due diligence checklist to help you plan with confidence. Let’s dive in.

Landmark basics in Old Town

Chicago’s local landmark designation is a municipal program run by the Commission on Chicago Landmarks and the City’s Landmarks Division. When a building or district is designated, changes to exterior features that are visible from a public way are regulated.

Old Town includes locally designated historic areas, including the well-known Old Town Triangle historic neighborhood. If your property is inside a Chicago Landmark district, exterior work that affects character-defining elements like façades, windows, rooflines, porches, and storefronts will likely require review by Landmarks staff.

Local designation is different from a National Register listing. The Chicago Landmark ordinance regulates changes at the City level. A National Register listing is honorary and does not restrict private work by itself, though it can connect certain projects to potential tax incentives for income-producing properties.

What the City reviews

The City focuses on exterior features visible from a public way such as streets, alleys, and parks. Interior work is generally outside landmark review unless it affects the exterior appearance or the structure in a way that changes what you see from the public way.

Common items that trigger review include:

• Demolition or partial demolition
• New construction, additions, or rooftop changes visible from the street or alley
• Masonry repairs, cornice work, porches, stoops, and façade alterations
• Windows and doors, including replacement, new openings, or size/profile changes
• Roofing if visible from a public way
• Storefront work, signage, and exterior mechanical equipment where visible

Emergency stabilization and safety work is recognized by the City, but you are expected to notify Landmarks staff and follow required approval procedures as soon as possible afterward.

Windows in vintage Old Town buildings

Windows are one of the most common and closely reviewed items in Old Town’s historic buildings. The general policy favors repair over replacement. If replacement is necessary, the new units should match the original appearance when viewed from the street.

What that means in practice:

• Aim to repair first. Typical preservation work includes patching, consolidating wood, reglazing, reweighting sash, and weatherstripping. Historically appropriate storm windows are often used to boost energy performance while retaining original sash.
• If replacing, match the look. Replacement windows should replicate original proportions, sightlines, muntin patterns, and operation. Wood is commonly preferred where historically accurate. High-quality alternatives, such as aluminum-clad wood or certain fiberglass products, may be acceptable if they match the visual profile.
• Energy upgrades are possible. Double-glazing can be compatible if it maintains the historic appearance. Interior or exterior storm windows are a common energy solution.
• Vinyl is often discouraged. Many vinyl products do not match historic profiles well. Even high-quality vinyl can be rejected if it fails to replicate the original look.

Documentation matters. Expect to provide photos, historic evidence, elevations or sections, and manufacturer specifications that show profiles and sightlines. If you are buying, ask for prior Certificates of Appropriateness and permits for any window work.

Approvals, permits, and timelines

For exterior work on a designated property, you typically need two approvals:

• A Certificate of Appropriateness (COA) from the Commission on Chicago Landmarks or an administrative approval by Landmarks staff.
• A building permit from the Chicago Department of Buildings for construction and alteration work.

Landmarks staff can approve many routine items administratively using published guidelines. Larger changes, demolitions, or projects that raise concerns usually go to the Commission for a public hearing. The Department of Buildings enforces building codes and safety requirements, but that does not replace Landmarks review.

Timelines vary based on scope and completeness. Staff-level approvals may take weeks. Cases that require Commission review can take months from first submission to final decision. Building permits are typically issued after your COA is granted for exterior work and once plans pass any required City plan review.

Enforcement has teeth. Work done without a COA or permit can lead to stop-work orders, fines, required reversals, and legal action by the City. Landmark protections run with the property, so future owners are subject to the same rules.

HOA approvals vs City approvals

Many Old Town condos and townhomes belong to associations that regulate exterior changes. HOA rules are private and contractual. City landmark rules are public and regulatory. In most cases, you need both.

Key differences and overlaps:

• HOAs can set stricter standards. Associations may specify brands, colors, or materials for uniformity, even beyond what the City requires.
• HOAs can regulate areas the City does not. Rear-yard elements or features not visible from the public way may still require HOA approval.
• One approval does not substitute for the other. A COA does not replace HOA approval, and HOA approval does not satisfy City requirements.

In practice, owners often seek HOA approval first to confirm compliance with building standards, then apply for the COA. Some associations will require you to show the COA before allowing installation.

Buyer checklist for HOAs:

• Ask for design standards, architectural review policies, and recent approval examples.
• Confirm responsibility for windows and building envelope in the declaration.
• Request disclosure of any outstanding violations or fines for exterior work.
• Review recent board minutes for any pending rule changes or enforcement issues.

Costs, value, and financing

Landmark status can support value by preserving historic character and the look of the streetscape. Many buyers actively seek vintage charm and consistent architectural context, which can help stabilize pricing on well-preserved blocks.

There are trade-offs. The buyer pool narrows for those who want to make modern exterior changes freely. Maintenance and historically appropriate replacements can cost more than commodity products. Plan for specialized contractors, custom materials, and a maintenance cycle that prioritizes repair over replacement.

Financing and insurance considerations:

• Lenders routinely finance landmark properties. If you plan major exterior changes, share timelines and scope early because approvals can affect construction schedules and costs.
• Insurance can be influenced by age and materials. Ask about coverage for historic features and replacement costs.
• Incentives exist mainly for income-producing properties. Federal and state rehabilitation credits typically apply to commercial or rental projects. Local grants or loans can be available at times through preservation organizations or municipal programs, but availability changes, so check current options.

Due diligence for buyers and owners

Whether you are buying or planning work, a little homework up front will save time and cost.

Steps to take before you buy:

• Verify landmark status through City resources or by contacting the Landmarks Division.
• Request copies of COAs, permits, and inspection reports for exterior work.
• Review the HOA declaration, bylaws, architectural rules, and recent minutes.
• Ask for maintenance history on windows, roof, masonry, and cornices.
• Confirm whether any violations or enforcement actions are outstanding.

Steps to take before you start work:

• Clarify what is visible from a public way. This determines whether Landmarks review applies.
• Secure HOA approval and align on any brand, color, or profile standards.
• Prepare documentation for the COA application, including photos and manufacturer specs.
• Engage an architect or contractor experienced with Chicago landmark projects.
• Build realistic timelines that account for both COA review and building permits.

Real-world scenarios to plan for

• Street-facing window replacement. Even if your windows were replaced decades ago, new units still need to match the historic appearance from the street. Expect documentation and possible product samples.
• Alley-facing changes. Alterations visible from an alley are typically considered visible from a public way. Rear windows or rooftop equipment facing the alley can trigger review.
• Masonry and cornice work. Tuckpointing, stone or brick repairs, and cornice restoration are reviewed to ensure compatible materials, mortar, and profiles.
• Storefront or signage updates. Ground-level retail in mixed-use buildings often requires careful storefront and sign design to match historic character while meeting current needs.
• Emergency repairs. Stabilize first, then notify Landmarks staff and follow the City’s process to document and approve the work.

Ready to plan your Old Town project?

If you own or are considering a vintage condo or townhome in Old Town, planning ahead is your best advantage. Align your HOA requirements with the City’s review process, budget for historically appropriate solutions, and build a clear plan for approvals and permits. A thoughtful approach protects your investment and keeps your project on schedule.

If you want help mapping next steps or evaluating a property before you commit, connect with Scott Broene for a neighborhood consultation and market perspective tailored to your goals.

FAQs

Do I need approval to replace windows in Old Town?

• Yes. If your building is in a Chicago Landmark district and the windows are visible from a public way, you will likely need a Certificate of Appropriateness and a building permit.

How can I confirm if my property is in a landmark district?

• Check City resources such as maps or contact the Landmarks Division directly, then verify details with your HOA and request any past COAs and permits from the seller or property manager.

How long does the Chicago COA process take for exterior work?

• Staff-level approvals can be weeks if your application is complete; projects requiring Commission hearings can take months, plus time for building permits.

Are interiors regulated in Old Town landmark properties?

• Generally no, unless interior work changes the exterior appearance or affects structural elements that alter what is visible from the public way.

Who is responsible for window costs in a condo building?

• It depends on the condominium declaration. Some HOAs handle the building envelope, while others assign sash or window components to unit owners.

What happens if prior owners changed windows without approvals?

• The City can enforce against unapproved work, and issues can follow the property. Check for violations, assess compliance, and plan for corrective steps if required.