Cedar Shake Roof Replacement Costs in 2026: What Chicago Homeowners Actually Pay

National roofing cost averages are almost useless for Chicago homeowners planning a cedar shake replacement.

The figures you find online blend data from every region, climate, and market. They mix basic ranch homes with complex multi-story structures. They combine budget materials with premium products.

The result? Numbers that don’t match any actual quote you’ll receive.

If you own a home in Barrington, Winnetka, Hinsdale, or another North Shore or western suburb community, you’re operating in a specific market with specific cost factors. Here’s what cedar shake replacement actually costs in this area in 2026, what creates the price spread between contractors, and how to evaluate the quotes you receive.

For a typical Chicago-area home with a cedar shake roof, replacement costs in 2026 generally fall into these ranges:

Replacing cedar shake with new cedar shake:

• Moderate complexity home (2,000 to 2,500 sq ft roof area): $45,000 to $65,000
• Larger or complex home (3,000 to 4,000 sq ft roof area): $70,000 to $110,000
• Estate properties (4,500+ sq ft roof area with high complexity): $120,000 to $180,000+

Replacing cedar shake with synthetic shake (DaVinci, Brava):

• Moderate complexity home: $50,000 to $75,000
• Larger or complex home: $80,000 to $130,000
• Estate properties: $140,000 to $200,000+

Replacing cedar shake with architectural asphalt shingles:

• Moderate complexity home: $25,000 to $40,000
• Larger or complex home: $45,000 to $70,000
• Estate properties: $75,000 to $100,000+

These ranges are wide because roofing costs depend on far more than square footage. Two homes with identical roof areas can have quotes $30,000 apart based on the factors below.

When homeowners collect multiple quotes, they often see significant variation. One contractor quotes $55,000. Another quotes $78,000. A third comes in at $62,000.

This isn’t random. Each number reflects specific choices about materials, methods, and service levels. Understanding what drives these differences helps you compare quotes fairly.

Not all cedar shake is the same.

Cedar grades:

• Premium grade (#1 Blue Label): 100% edge grain, no defects, longest lifespan. This is what most homeowners picture when they think of cedar shake. It costs the most.
• Standard grades (#2, #3): More variation in grain orientation, some knots permitted, shorter expected life. Lower cost but more maintenance and earlier replacement.
• Tapersawn vs. hand-split: Tapersawn shakes have a smoother face and more uniform appearance. Hand-split shakes have the traditional rough texture. Both are legitimate choices. Pricing varies by availability and preference.

Source matters:

• Western red cedar from British Columbia remains the standard for quality. Supply chain disruptions over the past several years have affected availability and pricing.
• Some contractors substitute lower-quality cedar from other sources. It looks similar at installation but weathers differently.

The cedar on a $52,000 quote may not be the same cedar on a $68,000 quote. Ask specifically about grade, source, and thickness.

Cedar shake is heavy. Removing an old cedar roof generates significant debris that must be loaded, hauled, and disposed of properly.

Factors affecting tear-off costs:

• Multiple layers: If a previous owner roofed over existing material (against best practice but it happens), removal costs increase substantially.
• Deck condition: Old cedar roofs often have skip sheathing (spaced boards) rather than solid plywood. Converting to solid sheathing for a new roof adds material and labor.
• Access difficulty: Steep driveways, landscaping obstacles, or tight lot lines make debris removal harder and slower.
• Disposal fees: Landfill tipping fees vary by county and have increased in recent years. Some contractors include this in their base price. Others list it as a separate line item.

A quote that seems low may exclude adequate allowance for tear-off complexity. Ask what’s included and what might create additional charges.

The roof deck is the structural layer beneath your shingles or shakes. On older cedar roofs, deck problems are common.

What inspectors often find under old cedar:

• Rot around penetrations: Areas near chimneys, vents, and skylights frequently show moisture damage.
• Valley deterioration: Valleys concentrate water flow. Deck rot in valleys is common on aging roofs.
• General deterioration: Decades of small leaks, condensation, and moisture exposure take a toll.
• Skip sheathing issues: The original spaced boards may have warped, cracked, or rotted in spots.

Honest contractors address deck condition in their quotes. Some include an allowance for typical repairs. Others quote the roofing work separately and price deck repairs per sheet of plywood if needed.

Understanding why decks fail helps you evaluate what’s actually needed versus what’s being oversold.

Red flag: A contractor who quotes without inspecting the attic or discussing potential deck issues is either inexperienced or planning to surprise you with charges later.

Square footage alone doesn’t capture the work involved in a roofing project. Two 3,000 square foot roofs can require vastly different labor hours.

Complexity factors:

• Pitch (steepness): Steeper roofs require more safety equipment, slower movement, and specialized techniques. Labor costs increase significantly above 8:12 pitch.
• Cut-up factor: Every valley, hip, dormer, and direction change requires cutting, fitting, and flashing. A roof with twelve planes takes far longer than a simple gable roof of the same area.
• Penetrations: Chimneys, skylights, vent stacks, and other penetrations each require custom flashing work.
• Height and access: Three-story homes require longer ladders, more equipment, and additional safety measures.
• Architectural details: Eyebrow dormers, turrets, curved sections, and decorative elements demand skilled craftsmanship.

Homes in established North Shore neighborhoods often have complex rooflines. Colonial Revivals, Tudors, and custom designs from the 1920s through 1990s frequently feature steep pitches, multiple dormers, and intricate details.

A flat-rate-per-square-foot quote on a complex roof means the contractor either hasn’t looked carefully or is planning to cut corners.

Flashings protect every vulnerable transition point on your roof. Material choice affects both cost and longevity.

Flashing options:

• Aluminum: Lowest cost, adequate for short-term applications, can corrode in contact with masonry or treated wood.
• Galvanized steel: Moderate cost, eventually rusts, not ideal for long-term premium installations.
• Copper: Highest cost, longest lifespan (50+ years), appropriate for premium roofing materials meant to last decades.
• Lead-coated copper: Premium option for specific historic applications.

If you’re investing in a cedar shake or synthetic roof meant to last 30 to 50 years, installing aluminum flashings that might fail in 15 years doesn’t make sense. But copper flashings add meaningful cost to a project.

Ask what flashing material is specified. “We use quality flashings” isn’t an answer. Get the specific material named.

Proper attic ventilation extends roof life and prevents moisture problems. As inspection data consistently shows, inadequate ventilation is one of the leading causes of premature roof failure.

Ventilation work that may be needed:

• Adding or enlarging soffit vents
• Installing ridge vent systems
• Adding gable or roof vents
• Correcting bathroom fans that vent into the attic
• Installing baffles to keep insulation from blocking airflow

Some contractors include ventilation assessment and correction in their scope. Others treat it as an add-on. Either approach can be legitimate, but you need to know what you’re comparing.

A roof quote that ignores ventilation may deliver a lower number but sets up the new roof for shortened life.

Labor is the least visible cost factor and often the most important.

What separates installation quality:

• Employee crews vs. subcontractors: Companies using trained employees typically deliver more consistent quality than those using pickup crews paid by the job.
• Experience with premium materials: Cedar shake and synthetic installation differs from asphalt shingle work. Crews experienced in premium materials produce better results.
• Time on site: Quality installation takes time. A crew that finishes a complex roof in two days is cutting corners. The same project done right might take four or five days.
• Supervision and quality control: Dedicated project managers who inspect work in progress catch problems before they’re buried under the next layer.

Two quotes with similar line items can represent very different installation quality. This is hard to evaluate from paperwork alone, which is why references from similar completed projects matter.

Beyond general cost factors, certain situations create price variation for individual homeowners.

Timing and scheduling:

• Peak season (late spring through early fall) typically brings higher prices and longer wait times.
• Contractors may offer better pricing for projects that can be scheduled flexibly.
• Emergency or rushed timelines cost more than planned replacements.

Project bundling:

• Combining roof replacement with gutter installation, chimney work, or other exterior projects sometimes reduces total cost compared to separate projects.
• Larger scope may allow contractors to offer better pricing.

Geographic location:

• Labor costs vary somewhat across the Chicago metro area.
• Disposal fees differ by municipality.
• Some communities require additional permits or inspections.

Home characteristics:

• Historic district requirements may limit material choices or require specific methods.
• HOA restrictions can affect material selection.
• Unusual architectural features require specialized skills.

When you receive multiple quotes, direct price comparison often misleads. A lower number isn’t better if it represents lesser materials, excluded work, or inexperienced installation.

Create an apples-to-apples comparison:

1. Verify material specifications. Are all contractors quoting the same cedar grade? The same underlayment? The same flashing material?
2. Check scope completeness. Does each quote include tear-off, disposal, deck repair allowance, new flashings, ridge vent, drip edge, and cleanup?
3. Understand contingencies. How does each contractor handle unforeseen deck damage? Is there an allowance built in, or will you face add-on charges?
4. Evaluate warranty terms. What workmanship warranty is provided? What voids it? Does the contractor have a track record suggesting they’ll still be in business to honor it?
5. Assess the company. How long have they been operating? Do they specialize in premium roofing or primarily do insurance claim work? Can they provide references for similar projects?

The best value often isn’t the lowest price. It’s the price that reflects quality materials, complete scope, skilled installation, and a contractor who stands behind their work.

Before committing to any contractor, get clear answers to these questions:

About materials:

• What cedar grade and source are you specifying?
• What underlayment will be used? Ice and water shield in what locations?
• What material are the flashings?

About the work:

• Who will actually perform the installation? Employees or subcontractors?
• What is your typical crew size and expected project duration?
• How do you handle deck damage discovered during tear-off?

About protection:

• What is your workmanship warranty term?
• Can you provide your insurance certificate?
• Will you pull the permit, or is that my responsibility?

About the company:

• How long have you been doing cedar shake installations?
• Can you provide references from projects similar to mine?
• Are you certified by any material manufacturers?

A contractor who answers these questions confidently and completely deserves serious consideration. One who deflects, gets vague, or pressures you to decide quickly deserves skepticism.

Cedar shake replacement is a significant investment. For many Chicago-area homeowners, it’s one of the largest single expenditures they’ll make on their home.

The goal isn’t to find the cheapest option. It’s to find the right option: appropriate materials, thorough workmanship, and a contractor who will execute properly and stand behind the result.

Understanding what affects roof lifespan helps you weigh the long-term economics, not just the upfront cost.

If you’re evaluating cedar shake replacement or considering alternatives like synthetic shake that offer similar aesthetics with different maintenance requirements, professional guidance helps you match the right solution to your specific home and goals.

Request a detailed assessment and estimate that explains not just the price, but what’s driving it and what you’ll receive for your investment.

Wolf Development provides premium roofing services throughout Chicago’s North Shore and western suburbs. We specialize in cedar shake, synthetic shake, slate, and other high-end roofing systems for discerning homeowners who expect quality materials, skilled installation, and straightforward communication.