Top 10 Roof Replacement in Chicago, IL

Updated March 2026 · Based on licensing, reviews & response time

Quick Answer

The best roof replacement companies in Chicago, IL for 2026 include Chicago Roofing Company (5), Anchor Point Roofing (5), Chicago Flat Roofing Contractors | Residential & Commercial Roofing Repairs (4.9). All handle full tear-off and replacement with manufacturer-certified installation warranties.

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1

Chicago Flat Roofing Contractors | Residential & Commercial Roofing Repairs

1347 N Western Ave, Chicago, IL 60622, USA
★★★★½ 4.9 (136 reviews)
Licensed & InsuredTop Rated
Services: Roof Replacement
2

Chicago Roofing Solutions

1655 S Blue Island Ave Ste 340, Chicago, IL 60608, USA
★★★★½ 4.6 (157 reviews)
Licensed & InsuredTop Rated
Services: Roof Replacement
3

Anchor Point Roofing

3104 N Sheffield Ave, Chicago, IL 60657, USA
★★★★★ 5 (238 reviews)
Licensed & InsuredTop Rated
Services: Roof Replacement
4

Chicago Roofing Company

4222 N Keystone Ave, Chicago, IL 60641, USA
★★★★★ 5 (93 reviews)
Licensed & Insured
Services: Roof Replacement
5

TAR Roofing Inc

3101 N Lincoln Ave, Chicago, IL 60657, USA
★★★★½ 4.9 (216 reviews)
Licensed & Insured
Services: Roof Replacement
6

Roofing By Hernandez

3033 N Clark St, Chicago, IL 60657, USA
★★★★½ 4.7 (190 reviews)
Services: Roof Replacement
7

Reliable Roofing

3605 N Damen Ave, Chicago, IL 60618, USA
★★★★★ 5 (49 reviews)
Services: Roof Replacement
8

Edwin's Roofing and Gutters PLLC

4702 W Ohio St, Chicago, IL 60644, USA
★★★★★ 5 (204 reviews)
Services: Roof Replacement
9

Perez Roofing & Masonry

4926 S Damen Ave, Chicago, IL 60609, USA
★★★★½ 4.8 (76 reviews)
Services: Roof Replacement
10

Chicago Prestige Roofing

2038 S Halsted St Suite 2, Chicago, IL 60608, USA
★★★★★ 5 (70 reviews)
Services: Roof Replacement

How We Ranked These Chicago Pros

Our rankings are based on a weighted evaluation of five key factors:

  1. Licensing & Insurance — All listed businesses hold active state licenses verified through official databases.
  2. Customer Reviews — We aggregate ratings from Google, Yelp, and the BBB, weighting recency and review volume.
  3. Response Time — Companies offering same-day or 24/7 emergency service score higher.
  4. Pricing Transparency — Businesses who offer flat-rate pricing or free estimates rank above those with opaque billing.
  5. Experience & Longevity — Years serving the Chicago market and breadth of services factor into overall reliability.

Rankings are reviewed quarterly. Have a correction? Contact us.

Frequently Asked Questions

How much does roof replacement cost in Chicago?

Roof replacement in Chicago costs $5,000-$15,000 for asphalt shingles on a standard home (1,500-2,500 sq ft). Metal roofing costs $10,000-$25,000. Tile or slate costs $15,000-$40,000+. Price depends on roof size, pitch, material, and tear-off complexity.

How long does roof replacement take?

Most residential roof replacements take 1-3 days. Complex roofs (steep pitch, multiple layers to tear off, custom materials) take 3-5 days. Weather delays can extend the timeline.

When should I replace my roof?

Replace when: shingles are 20-25+ years old, multiple leaks, widespread damage (storm/hail), sagging decking, or repair costs exceed 30% of replacement cost. A roof inspection can tell you remaining lifespan.