Most homeowners in the Chicago area pay somewhere between $12,000 and $25,000 for a full roof replacement with standard asphalt shingles, with the total driven mainly by roof size, pitch, material, and how many layers of old roofing need to come off first. Premium materials like metal, cedar, or slate run significantly higher — often $20,000 to $40,000 or more, depending on the roof.

That's a wide range on purpose — the only way to get a number you can actually budget around is a free inspection, since two houses with the "same size" roof can have very different costs once pitch, layers, and access are factored in.

What actually drives the cost​

  • Roof size. Cost is typically calculated by the "square" (100 square feet of roof area) — more squares means more material and labor.
  • Material. Asphalt shingles are the most affordable. Impact-resistant (Class 4) shingles cost somewhat more but can qualify for insurance discounts. Metal, cedar shake, and slate or tile all cost meaningfully more, with slate and tile at the top of the range.
  • Roof pitch. Steeper roofs are slower and more complex to work on safely, which adds labor cost.
  • Layers of tear-off. Removing one layer of old shingles is far cheaper than removing two, and any decking damage found underneath adds to the scope.
  • Roof features. Chimneys, skylights, valleys, and dormers all add complexity compared to a simple, single-plane roof.
  • Timing. Late summer and early fall are peak season for roofing demand in the Chicago area; scheduling in winter or early spring sometimes means better pricing and faster availability.

A quick breakdown by material​

  • Asphalt shingles: The most common and most affordable choice for the Chicago area.
  • Impact-resistant (Class 4) shingles: A moderate step up in cost, often partly offset by insurance premium discounts.
  • Metal roofing: A bigger jump in upfront cost, offset by a much longer lifespan — often 40 to 70 years — and strong performance against Chicago's freeze-thaw cycles.
  • Cedar shake, slate, and tile: The most expensive options, typically chosen to match an existing high-end roofline or for their distinct look and longevity.

How to get an exact number

General ranges are useful for early budgeting, but the only accurate quote comes from someone who's actually looked at your specific roof. RS Five offers a free AI-powered drone inspection with a full Roof Condition Report — normally a $299 value, offered at no charge — so you can get a real number without climbing a ladder or committing to anything.

Frequently asked questions

Is it cheaper to repair than replace?
Sometimes — it depends on the extent of the damage, the roof's age, and how much of the roof is affected. A professional inspection is the most reliable way to know which makes more sense for your situation.

Does roof size directly determine the price?
It's one of the biggest factors, but not the only one — a small, steep, complex roof can cost more than a larger simple one.

Will my roof replacement cost more if I file an insurance claim?
Not inherently — the cost of the work is the cost of the work. What changes with an insurance claim is how much of that cost you're responsible for out of pocket, which depends on your deductible and coverage.

Last updated: August 2026. Cost ranges reflect general Chicago-area market conditions and will vary by project. For an exact, no-obligation quote, schedule a free AI drone roof inspection with RS Five.