A Chicago winter finds every weak spot in a roof, and by the time you see a stain on the ceiling the damage is usually older than the drip. Anchor Point Roofing tops this list of roofing contractors in Chicago with a perfect 5.0 across 244 reviews, exactly double the smallest review count on the page, and every name here still holds at least a 4.6. When the numbers are this close at the top, what separates them is how fast they answer the phone once the leak starts.
Short answer: The top-scoring roofer in Chicago is Anchor Point Roofing (a perfect 5.0 across 244 Google reviews, the most of any contractor here), followed by TAR Roofing (4.9, 224 reviews) and Roofing By Hernandez (4.7, 191). For a full asphalt-shingle roof replacement in 2026, most Chicago homeowners land somewhere between $8,000 and $25,000, with flat-roof and repair jobs costing less.
#1 Overall🕑 Open 7 days
Anchor Point Roofing
5.0★★★★★244 Google reviews
Anchor Point Roofing is a Chicago roofing company on North Sheffield Avenue handling both residential and commercial work, from minor repairs to full replacements. It covers asphalt shingle and flat roofing systems, chimney flashing and storm damage, and runs free inspections before quoting. Reviewers describe a tech-forward process with photos and updates at each stage, led by owner Jim and project contacts like Ever.
What people praise
- Free inspections with honest assessments, even when the roof is fine
- Photos and updates shared before, during and after the job
- Reviewers report fair, competitive quotes
- Fast turnarounds, some replacements done in a day
- Named as the most honest of several bids by more than one homeowner
Worth knowing
- Demand can mean scheduling around weather and the calendar
Reputation scorecardrank in Chicago
Info completenesssite · phone · hours
Rating breakdown99% 5-star
✓ VerifiedSource: Google
Our take: The top score on this list, with a perfect rating on the largest review base of any Chicago roofer here. The safe default for both repairs and a full replacement.
📍3104 N Sheffield Ave, Chicago, IL 60657
#2🕑 Open 6 days/wk
TAR Roofing Inc
4.9★★★★★224 Google reviews
TAR Roofing is a roofing company serving Chicago and the northwest suburbs, specializing in residential roof repair and replacement plus siding, gutters and fascia work. It positions itself around honest evaluations and solid craftsmanship, with long daily hours six days a week. Repeat customers describe using the team across several projects over the years.
What people praise
- Responsive from quote through completion
- Reviewers call the pricing fair and the cleanup thorough
- Handles roofing plus siding, gutters and skylights
- A base of repeat customers who return for new projects
Worth knowing
- A minority of reviews describe disputes over complex flat-roof replacements, so get the warranty terms in writing
Reputation scorecardrank in Chicago
Info completenesssite · phone · hours
Rating breakdown95% 5-star
✓ VerifiedSource: Google
Our take: A near-perfect rating on a deep review base and a strong all-rounder for roof, siding and gutter work together. Confirm the written warranty on flat-roof jobs before work starts and you get a well-reviewed, versatile contractor.
📍3101 N Lincoln Ave, Chicago, IL 60657
#3🕑 Open 5 days/wk
Roofing By Hernandez Inc
4.7★★★★★191 Google reviews
Roofing By Hernandez is a Chicago roofing contractor on North Clark Street handling repairs, full replacements, flat roofs and deck work for homes across the area. Reviewers describe owner Ivan and the crew providing detailed, itemized quotes with insurance documentation up front, and the team is noted for careful work on flat roofs and rooftop decks. Several homeowners have used them across multiple projects.
What people praise
- Detailed, itemized quotes with insurance paperwork included
- Strong on flat roofs and rooftop deck work
- Crews reviewers describe as on-time, tidy and professional
- Repeat customers across separate jobs
Worth knowing
- A few reviews raise unresolved warranty concerns on preventative work, so clarify the coverage
- Closed weekends
Reputation scorecardrank in Chicago
Info completenesssite · phone · hours
Rating breakdown89% 5-star
✓ VerifiedSource: Google
Our take: A well-rated pick with a reputation for thorough quotes and flat-roof skill. It ranks third on a blend of rating and volume. Nail down the warranty terms and it's a dependable choice.
📍3033 N Clark St, Chicago, IL 60657
#4🕑 Open 7 days
Chicago Roofing Solutions
4.6★★★★★162 Google reviews
Chicago Roofing Solutions is a family-owned, 24/7 roofing company with 20-plus years serving the city and suburbs, running roof construction, maintenance and repair across residential and commercial properties. It advertises same-day emergency response, and reviewers describe owner John and the crew handling urgent leaks quickly, including snow and ice damage. The service area spans much of Chicagoland.
What people praise
- Same-day and 24/7 emergency response reported
- Two decades in business across a wide service area
- Reviewers praise clear options and honest recommendations
- Handles residential, commercial and condo roofs
Worth knowing
- A minority of reviews describe post-repair leak disputes, so get the fix and warranty documented
Reputation scorecardrank in Chicago
Info completenesssite · phone · hours
Rating breakdown88% 5-star
✓ VerifiedSource: Google
Our take: A practical pick when a leak can't wait, backed by long experience and around-the-clock scheduling. It ranks fourth here. Put the scope and warranty in writing before the crew starts.
📍1655 S Blue Island Ave Ste 340, Chicago, IL 60608
#5🕑 Open 7 days
Chicago Flat Roofing Contractors | Residential & Commercial Roofing Repairs
4.8★★★★★122 Google reviews
Chicago Flat Roofing Contractors is a North Western Avenue company focused on flat roofing, with a line in TPO, EPDM, modified bitumen, rooftop decks and 24/7 emergency repairs across residential and commercial buildings. It advertises licensed, bonded and insured work with same-day response. Reviewers describe clean, on-schedule roof replacements and quick emergency callouts for insurance-related repairs.
What people praise
- Focused specialist in flat and low-slope roofing systems
- Reviewers report clean job sites and on-time completion
- 24/7 emergency and same-day response
- Clear walkthroughs of long-term repair and replacement options
Worth knowing
- A smaller review base than the names above it
Reputation scorecardrank in Chicago
Info completenesssite · phone · hours
Rating breakdown95% 5-star
✓ VerifiedSource: Google
Our take: Its 4.8 rating actually tops the two contractors ranked above it, but on fewer reviews, which is why it lands fifth on proven volume rather than higher. A strong shortlist pick specifically for flat and low-slope roofs.
📍1347 N Western Ave, Chicago, IL 60622
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Claim this spot › How we score
Every number on this page is computed from public Google data on the date shown, not from opinion or payment. Rating is the contractor’s live Google star average. Review volume is how many customers have rated them, ranked against other Chicago roofers. Confidence weighs the rating by that volume, so a 5.0 from 244 people carries more weight than a 4.8 from 122. Recency reflects how recently customers are still leaving reviews. No contractor can pay to change these numbers.
How much does a new roof cost in Chicago? (2026)
Chicago roofing prices swing with the roof’s size, pitch, material and how much decking underneath needs replacing. Flat-roof systems and repairs cost less than a full tear-off. Here are current 2026 ranges for common jobs:
| Job | Typical price |
|---|
| Roof inspection / estimate | Often free |
| Minor repair (flashing, small leak) | $400 - $1,500 |
| Asphalt shingle roof (replacement, installed) | $8,000 - $25,000 |
| Flat roof (TPO / EPDM, replacement) | $8,000 - $18,000 |
| Gutter replacement | $1,200 - $4,000 |
| Emergency / storm tarping | $400 - $1,500 |
Ranges compiled July 2026 from Angi, HomeGuide and Fixr, cross-checked against price assessments in Chicago customer reviews (roughly $4,000 to $18,000 on recent replacements). Roof size, pitch and hidden decking damage move the final number, so always get an itemized written quote.
Serving Chicago and Chicagoland
The contractors above cover Chicago and the surrounding suburbs, including Lincoln Park, Lakeview, Wicker Park, Logan Square, Pilsen and out into Evanston, Skokie, Oak Park and the northwest suburbs. Searching for a roofing contractor near me? Every listing below shows a live phone number and directions, so you can reach the closest crew fast when a leak won’t wait.
What to ask before you hire a roofer
- Are you licensed, bonded and insured in Illinois? (Ask for proof.)
- Is the quote itemized, and does it cover decking replacement if needed?
- What warranty do you offer on materials and on labour?
- Will you handle the insurance paperwork for storm damage?
- Who supervises the crew on site, and what’s the timeline?
- How do you protect the property and handle cleanup and nail sweep?
Frequently asked questions
How did you choose these roofing contractors?
We started from the Chicago roofers with a real public Google presence, then ranked by rating, review volume, consistency and recency. See How we score above.
Are these rankings paid?
No. Rankings come from the public Google data in the scorecard. A contractor can pay to be a Featured Partner, which adds a badge and top placement, but that never changes another contractor’s score or position.
How often is this updated?
The data carries a verified date, July 2026 on this page. We refresh listings periodically so ratings and review counts stay current.
How much does a new roof cost in Chicago?
Most full asphalt-shingle replacements land between $8,000 and $25,000 in 2026, with flat-roof systems and repairs costing less. Size, pitch and hidden decking damage drive the price, so get an itemized written quote. See the cost table above.
Do Chicago roofers offer emergency service?
Yes. Several here, including Chicago Roofing Solutions and Chicago Flat Roofing Contractors, advertise 24/7 emergency and same-day response for leaks and storm damage. Confirm availability and any callout fee when you phone.
The bottom line
Anchor Point Roofing is the safe default for most Chicago homeowners on a perfect rating and the deepest review base, while Chicago Flat Roofing Contractors is the specialist call for flat and low-slope roofs. Whoever you hire, get the quote itemized and the warranty in writing before the tear-off begins.
