Chicago Region
Drive through any Chicago neighborhood and look up. The two-flats of Wicker Park have flat roofs. The greystones of Lincoln Park have flat roofs. The three-flats of Rogers Park and Lakeview have flat roofs. The commercial buildings on Milwaukee Avenue, Western Avenue, and 63rd Street have flat roofs. Even the century-old apartment buildings of Hyde Park and Bridgeport — flat roofs. Chicago’s dominant building types were designed with flat or very low-pitch roof systems, and those systems fail in a specific way that pitched shingle roofs do not.
Flat roofs in Chicago contend with two forces that accelerate membrane failure faster than almost anywhere in the country. First: ponding water. After Chicago’s documented heavy summer storms — the July 23, 2011 event dropped 6.86 inches of rain at O’Hare in 24 hours, and the August 1987 event dropped 9.35 inches — water pools on flat surfaces and sits. Membrane punctures and seams that might go years without leaking under normal conditions fail quickly under standing water. Second: freeze-thaw cycling. Chicago temperatures oscillate above and below 32°F throughout winter and early spring. Water that entered a seam or crack during fall rains freezes and expands, widening the gap. This repeats dozens of times between October and April. By spring, a flat roof that looked acceptable in September may be actively leaking.
For homeowners and building owners in Chicago’s neighborhood districts, The ProGuide’s vetted roofing listings filter for contractors who pull Chicago permits, carry insurance, and have community reviews from actual customers — not contractors who mostly work in suburban new construction and occasionally take a city call.
Every listing screened for Chicago Department of Buildings permit compliance and insurance
Community sentiment compiled from verified customer reviews across the web
No lead-selling — you contact the contractor directly
Roofers serving Chicago and inner suburbs including Evanston and Oak Park
What to look for
- Permits Verified
- Insured
- Flat Roof Specialists
- EPDM & TPO
- Ice & Water Shield
- Emergency Tarping
Verified Rankings (October 4, 2026)
Your zip: 63122
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Top Roofers Near 6310110 Pros Found
Showing 10 results within 30 miles of 63101
| Rank▼ | TPG Score▼ | Company | Sentiment▼ | Ownership▼ | The ProGuide▼ | |||
|---|---|---|---|---|---|---|---|---|
 | #1 | TPG Score4.6 ✓✓✓The TPG Score is a proprietary 0–5 rating that blends community sentiment, review volume, ownership type, verification status and other signals | Tesson Roofing & Exteriors LLC Roofing, Siding, Gutters | Positive 780 ReviewsCommunity Sentiment 🟢 Thorough Walkthrough 🟢 Clean / Respectful 🟢 Upfront Quote 🟢 No-Pressure Sales | ✓Local | ✓Full Throttle! Full Throttle! Top-tier vendor with outstanding quality, service, and reputation. Recommendation: Everything checks out — proceed with confidence. | 314-271-7705Call Now | |
 | #2 | TPG Score4.4 ✓✓✓The TPG Score is a proprietary 0–5 rating that blends community sentiment, review volume, ownership type, verification status and other signals | Andres Roofing Roof Repairs, Hail & Storm … Roof Repairs, Hail & Storm Damage, Flashing Work, Roof Replacements, Ventilation, Skylights, Gutters | Positive 272 ReviewsCommunity Sentiment 🟢 Clean / Respectful 🟢 Upfront Quote | ✓Local | ✓Full Throttle! Full Throttle! Top-tier vendor with outstanding quality, service, and reputation. Recommendation: Everything checks out — proceed with confidence. | 314-228-5143Call Now | |
 | #3 | TPG Score4.3 ✓✓✓The TPG Score is a proprietary 0–5 rating that blends community sentiment, review volume, ownership type, verification status and other signals | St. Louis Residential Roofing Roof Replacement, Storm Damages… Roof Replacement, Storm Damages and Claims, Gutters, Downspouts, Gutter Covers | Positive 115 ReviewsCommunity Sentiment 🟢 Clean / Respectful 🟢 Thorough Walkthrough 🟢 Upfront Quote | ✓Local | ✓Full Throttle! Full Throttle! Top-tier vendor with outstanding quality, service, and reputation. Recommendation: Everything checks out — proceed with confidence. | 314-794-5291Call Now | |
 | #4 | TPG Score4.2 ~✓~The TPG Score is a proprietary 0–5 rating that blends community sentiment, review volume, ownership type, verification status and other signals | Stonebridge Roofing Residential Roofing, Commercial… Residential Roofing, Commercial Roofing, Roof Repairs, Roof Replacement, New Roof Installation, Metal Roofing, Roof Inspections, Emergency Roof Services, Hail Damage Repair, Roof Leak Repair, Roof Tarping, Storm Damage Roof Repair, Wind Damage Roof Repair, Tree Damage Roof Repair, Siding Installation, Siding Repair, Gutter Installation, Gutter Guard Installation, Gutter Repair | Mixed 381 ReviewsCommunity Sentiment 🔴 Poor Comms 🔴 Issue Unresolved 🟢 Upfront Quote | ✓Local | ~Buckle Up Buckle Up Vendor shows potential but has some concerns worth considering before moving forward. Recommendation: Proceed with caution and review details carefully. | 314-333-0619Call Now | |
 | #5 | TPG Score4.0 ~✓~The TPG Score is a proprietary 0–5 rating that blends community sentiment, review volume, ownership type, verification status and other signals | Frederic Roofing Company Roof Repair, Roof Replacement, … Roof Repair, Roof Replacement, Gutter Repair, Gutter Cleaning, Gutter Installation, Soffit Repair, Soffit Replacement, Storm Damage Repair | Mixed 267 ReviewsCommunity Sentiment 🟢 Thorough Walkthrough 🟢 Upfront Quote | ✓Local | ~Buckle Up Buckle Up Vendor shows potential but has some concerns worth considering before moving forward. Recommendation: Proceed with caution and review details carefully. | 314-557-2976Call Now | |
 | #6 | TPG Score4.0 ~✓~The TPG Score is a proprietary 0–5 rating that blends community sentiment, review volume, ownership type, verification status and other signals | Allen Roofing & Siding Residential Roofing, Commercial… Residential Roofing, Commercial Roofing, Siding, Gutters, Storm Damage Repair, Skylights, Tuckpointing | Mixed 253 ReviewsCommunity Sentiment 🟢 Thorough Walkthrough 🟢 Clean / Respectful 🔴 Poor Comms 🔴 Issue Unresolved | ✓Local | ~Buckle Up Buckle Up Vendor shows potential but has some concerns worth considering before moving forward. Recommendation: Proceed with caution and review details carefully. | 314-237-8153Call Now | |
 | #7 | TPG Score3.9 ~✓~The TPG Score is a proprietary 0–5 rating that blends community sentiment, review volume, ownership type, verification status and other signals | Innovative Construction & Roofing TPO/EDPM Roof Systems, Metal Ro… TPO/EDPM Roof Systems, Metal Roofing, Modified Bitumen Systems, Roof Repairs, Roof Replacement, Roof Maintenance, Siding, Exteriors, Custom Copper, Sheet Metal, Slate, Tile, Asphalt Shingles, Storm Restoration, Historical Restoration | Mixed 80 ReviewsCommunity Sentiment 🟢 Clean / Respectful 🟢 Upfront Quote 🔴 Issue Unresolved | ✓Local | ~Buckle Up Buckle Up Vendor shows potential but has some concerns worth considering before moving forward. Recommendation: Proceed with caution and review details carefully. | 314-403-1848Call Now | |
 | #8 | TPG Score3.7 ✗✓~The TPG Score is a proprietary 0–5 rating that blends community sentiment, review volume, ownership type, verification status and other signals | Big Bear Roofing Residential Roofing, Commercial… Residential Roofing, Commercial Roofing, Roof Replacement, Roof Repair, Soffits, Fascia, Shingles, Siding, Gutters, Metal Roofing, Flat Roofing, Storm Damage Repair | Negative 174 ReviewsCommunity Sentiment 🟢 Thorough Walkthrough 🟢 Clean / Respectful 🟡 Standard | ✓Local | ~Buckle Up Buckle Up Vendor shows potential but has some concerns worth considering before moving forward. Recommendation: Proceed with caution and review details carefully. | 314-936-3670Call Now | |
 | #9 | TPG Score3.6 ✗✓✗The TPG Score is a proprietary 0–5 rating that blends community sentiment, review volume, ownership type, verification status and other signals | Gallagher Bros Construction Roof Replacement, Residential R… Roof Replacement, Residential Roofing, Commercial Roofing, Specialty Roofing, Roof Repair, Silicone Roof Coating, Hail Damage Repair, Siding, Gutters, Gutter Guards, Window Replacement | Negative 672 ReviewsCommunity Sentiment 🟢 Thorough Walkthrough 🟢 Clean / Respectful 🟢 Upfront Quote 🔴 Delay Reported 🔴 Poor Comms 🔴 Issue Unresolved | ✓Local | ✗Off-Road Off-Road Vendor has significant concerns that may lead to a poor experience or added risk. Recommendation: We do not currently recommend moving forward. | 314-876-8534Call Now | |
 | #10 | TPG Score3.5 ✗~✗The TPG Score is a proprietary 0–5 rating that blends community sentiment, review volume, ownership type, verification status and other signals | Ferguson Roofing Roofing, Siding, Exterior Const… Roofing, Siding, Exterior Construction | Negative 397 ReviewsCommunity Sentiment 🔴 Poor Comms 🔴 Delay Reported 🔴 Issue Unresolved | ~Private Equity | ✗Off-Road Off-Road Vendor has significant concerns that may lead to a poor experience or added risk. Recommendation: We do not currently recommend moving forward. | 314-207-9646Call Now |
Compare Chicago Roofing Services
Chicago’s roofing market divides primarily between flat-roof systems on city buildings and pitched-roof systems on bungalows and single-family homes. The two require different materials, methods, and maintenance schedules.
Flat Roof Repair and Replacement
The flat roofs on Chicago two-flats, three-flats, and greystones are most commonly covered with one of three membrane systems: built-up roofing (BUR, the traditional tar-and-gravel system, common on pre-1980s buildings), EPDM (rubber membrane, dominant in residential flat roofing since the 1980s), or TPO (thermoplastic polyolefin, the current standard for commercial and residential flat applications). Modified bitumen is also common on older buildings. Repair work on flat roofs typically addresses seam failures, flashing separations at parapet walls, and membrane punctures. Replacement requires complete tear-off of existing materials and installation of a new membrane system with proper drainage specifications.
Parapet Wall and Flashing Repair
Chicago’s greystones, two-flats, and three-flats have parapet walls — the low brick walls that extend above the roof plane around the perimeter. Parapet walls develop cracks in mortar joints, and cap flashing where the roof membrane meets the parapet face is a chronic failure point. Water entering at the parapet-to-membrane junction is the most common source of interior water damage in flat-roof Chicago buildings. Tuckpointing the parapet masonry and re-flashing the base and cap are often required together.
Ice Damming on Chicago Bungalow Roofs
Chicago bungalows have low-pitched hipped roofs with wide overhangs — a design that sheds snow slowly. When heat escapes through the roof deck, snow melts from below and refreezes at the colder overhangs, building ice dams that force meltwater under shingles and into the structure. With Chicago averaging roughly 38 inches of annual snowfall and repeated freeze-thaw cycles through winter, ice damming is a recurring issue in bungalow-belt neighborhoods from Avondale to Beverly. Ice and water shield membrane at eaves, improved attic insulation and ventilation, and heat cables are the standard intervention set.
Shingle Roof Replacement
Chicago bungalows and single-family homes in Beverly, Bridgeport, and the outer neighborhoods have asphalt shingle roofs. Standard 3-tab shingles have been largely replaced in the market by architectural (dimensional) shingles, which have better impact resistance — relevant in Chicago’s hail-prone spring and summer storm season. Impact-resistant shingles rated Class 3 or 4 can qualify for insurance discounts in areas with frequent hail.
Storm Damage Assessment and Insurance Claims
Chicago’s severe thunderstorm season — the city averages nearly 38 thunderstorm days per year per the Illinois State Water Survey — produces hail events that damage roofing materials across the metro area. After significant hail events, roofing contractors should provide documented inspection reports that identify impact damage to shingles, metal flashing, and flat roof membranes. An experienced contractor can document damage in terms that support insurance claims rather than just noting “some hail hits.”
Emergency Tarping and Leak Response
Storm damage, ice dam failures, and acute membrane failures require rapid response to prevent interior water damage from escalating. Chicago roofing contractors who offer emergency tarping and leak response are meaningfully different from those who only schedule replacement work weeks out.
Request a quote from a listing that matches your issue, timeline, and budget.
Find a listed contractor now
the ProGuide Authority
Why Use Our Listings
Chicago’s flat-roof market is a specialty. A roofing company that excels at pitched-shingle replacement in Naperville may not have a crew experienced with EPDM membrane installation on a Rogers Park three-flat, parapet flashing repair on a Hyde Park greystone, or the specific ponding-water drainage design requirements of Chicago’s taller apartment buildings. The ProGuide’s two-layer model starts with what Chicago building owners actually say about their roofers — documented through community reviews — and filters for contractors who pull Chicago permits and carry adequate insurance.
Community-Informed Rankings
The ProGuide compiles homeowner and building owner reviews for roofing contractors working in Chicago’s specific neighborhood districts — the flat-roof neighborhoods of Wicker Park, Logan Square, Lakeview, Rogers Park, Pilsen, and Hyde Park as well as the bungalow-belt neighborhoods where pitched-roof and ice dam work is more common. Contractors who consistently earn strong reviews from Chicago building owners have demonstrated they understand the city’s roofing systems.
Professionally Vetted Profiles
Illinois does not require a state roofing contractor license. In Chicago, roofing work is permitted through the Chicago Department of Buildings — re-roofing of a certain scope requires a permit, and that permit is the primary regulatory checkpoint for quality and code compliance. Chicago roofing contractors are also subject to Illinois’s Home Repair and Remodeling Act (815 ILCS 513), which requires written contracts for work over $1,000. The ProGuide confirms permit compliance and insurance for all Chicago roofing listings.
Booking-Ready Information
Chicago roofing listings include direct contact information. You reach the contractor without a lead-form intermediary.
Local Relevance
Listings cover Chicago’s city neighborhoods and extend to served suburbs. Contractors specify their service area so you know whether they work in your zip code before calling.
What to Look for Before You Call
Credential Checks
Illinois has no state roofing contractor license. For Chicago, roofing permits are required for re-roofing and significant repair work, pulled through the Chicago Department of Buildings. Ask any roofing contractor you’re considering whether they pull permits for the work they’re quoting. Unpermitted roofing work can void manufacturer warranties and create complications at resale. Confirm insurance: roofing carries above-average injury risk, and an uninsured roofing crew working on your building creates liability exposure for you as the property owner.
The Flat Roof Fluency Test
This is the essential qualifying question for Chicago’s most common building types. If you own a two-flat, three-flat, greystone, or apartment building in any Chicago neighborhood, ask prospective roofers directly: what flat roof membrane systems do you install and repair? How do you design drainage for a flat roof on a building this size? How do you handle the parapet-to-membrane flashing transition? A contractor experienced with Chicago’s flat-roof building stock will answer these questions with specifics — membrane types and weights, tapered insulation design for drainage, flashing detail at parapets and HVAC curbs. A contractor whose primary experience is residential pitched-shingle work will talk around these questions or give vague answers. For Chicago’s most common building types, flat roof experience is not optional.
Quote and Pricing Signals
Flat roof replacement on a Chicago two-flat or three-flat typically runs $8,000 to $18,000 depending on square footage, membrane system selected, existing roof condition (layers to tear off), and parapet complexity. EPDM membrane replacement for a standard Chicago two-flat (approximately 1,200–1,500 sq ft) commonly falls in the $8,000–$12,000 range installed. Shingle replacement on a Chicago bungalow typically runs $6,000–$12,000 depending on pitch, access, and material grade. Get itemized quotes that separate tear-off, materials, flashing, labor, and permits. Ask whether the quote includes a drainage assessment and post-installation inspection.
Review Quality
Look for reviews from Chicago building owners who describe the specific roof type and the problem being addressed. Reviewers who mention that the contractor identified and addressed the parapet flashing, noted drainage issues, or provided documentation for an insurance claim are describing a contractor who understands Chicago’s roofing context.
Call a listed contractor once you have compared credentials, estimated quality, and overall service fit.
Find a listed contractor now
- Chicago building owners have used vetted roofing listings to find contractors for flat roof replacement, parapet repair, and storm damage assessment
- Reviewed contractors serving Wicker Park, Lincoln Park, Hyde Park, Rogers Park, Lakeview, Pilsen, and all Chicago neighborhoods
- No pay-to-play rankings — roofing companies appear based on permit compliance verification and community reputation
- Every listing confirms insurance before publication
- Chicago building owners report vetted contractors provide detailed written estimates and permit documentation
How It Works
the ProGuide Authority
Compare listings
Browse vetted Chicago roofers filtered by service type and neighborhood
Shortlist contractors
Read community reviews and verify credentials
Call or request a quote
Contact the contractor directly; no middleman
Review the estimate
Compare itemized quotes before committing
Chicago Roofing — Flat Membranes, Freeze-Thaw, and the Buildings That Define This City
Chicago
Chicago’s architectural character is defined by its residential building types: the Chicago bungalow, the greystone, the two-flat, the three-flat. All of them share a roofing characteristic that distinguishes this market from virtually any other major U.S. city — they are predominantly flat-roofed buildings in a climate that punishes flat roofs severely.
The physics of flat roofing in Chicago work like this. A pitched roof sheds rain and snowmelt by gravity; water moves off the surface before it can saturate seams or dwell at membrane edges. A flat roof relies on internal drainage — roof drains, scuppers, or controlled slope built into the roof deck — to move water off before it ponds. When drains clog, when the slope is inadequate, or when the roof substrate has settled unevenly over decades, water sits. The average July in Chicago brings over three inches of rain; the city has documented multi-inch rainfall events that have overwhelmed drainage systems across entire neighborhoods.
Freeze-thaw cycling compounds membrane stress throughout the winter and early spring. Chicago temperatures oscillate above and below 32°F repeatedly from November through March — sometimes multiple times in a week during the transitional months. Water that has entered a membrane seam, a flashing gap, or a parapet crack expands as it freezes. When it thaws, the gap is slightly wider. Over a Chicago winter with dozens of freeze-thaw cycles, what started as a hairline failure becomes an active leak path. Flat roof membranes in Chicago age faster than they would in milder climates; a 20-year roof warranty reflects average conditions, not Chicago’s.
Parapet walls — the low brick parapets around the perimeter of Chicago’s flat-roofed buildings — present their own maintenance challenge. Parapet masonry deteriorates through freeze-thaw action on mortar joints; cap flashing at the top of the parapet and base flashing where the roof membrane meets the parapet face are the most failure-prone details on any Chicago flat-roof building. Water entering at a deteriorated parapet can travel laterally inside the wall cavity before appearing as interior water damage well away from the source.
Chicago bungalows add a different dimension: pitched roofs under heavy snow load. The bungalow’s distinctive low-pitched hipped roof with wide overhangs sheds snow slowly. The combination of heat loss through poorly insulated attic spaces and Chicago’s freeze-thaw cycling creates ideal conditions for ice dam formation — ice builds at the eaves, forces meltwater back under shingles, and drives water into the structure. Neighborhoods like Avondale, Logan Square, and Beverly report recurring ice dam issues on older bungalows with original attic insulation levels.
The contractors who understand this market know that Chicago roofing is not primarily about shingles. It’s primarily about membrane integrity, drainage design, parapet maintenance, and freeze-thaw resilience.
FAQ
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Find a Vetted Roofing Contractor in Chicago Today
Whether you need a flat roof replacement on a Wicker Park two-flat, parapet flashing repair on a Hyde Park greystone, or ice dam remediation on a Beverly bungalow, The ProGuide’s vetted listings connect you with reviewed, insured roofing contractors who understand Chicago’s building types.
Find a Listed Contractor Now