The Best Roofing Contractors in Chicago, IL, Compared

It depends on the roof's size, pitch, number of layers to remove, decking condition and the material you choose. In Chicago, architectural shingles with full ice-and-water underlayment are the most common replacement, with standing-seam metal as the step-up option. Get at least two itemized written estimates from the contractors on this page; a serious estimate lists the underlayment, flashing, ventilation and decking price per sheet, not just a lump sum.

In most of Cook County a full replacement requires a building permit and at least one inspection; small repairs often do not. The contractor should pull the permit in their name. If a roofer asks you to pull it as the homeowner, treat that as a warning sign about their license or insurance.

Chicago has a large share of flat and low-slope roofs on two- and three-flats. Residential roofing inside the city requires a licensed roofing contractor and a city permit. The region's usual problems are ice dams, snow load, freeze-thaw cycling and spring wind. Roofing season is roughly April through November. Ice dams in January are usually an attic insulation and air-sealing problem, not a shingle problem, so the right fix often starts inside.

Ice-dam interior damage is often covered; the roof repair itself usually is not. Keep photos and get the contractor's written cause-of-loss note. Document everything with photos before any work starts, and never sign an assignment of benefits or a contract contingent on an insurance approval without reading it.

Ask for the certificate of insurance directly from the insurer, not a copy from the contractor, and confirm it lists both general liability and workers' compensation. Look the license up on the Illinois contractor licensing board site, and check the local address matches what the board has on file.