Flashing, Chimney & Skylight Repair in Chicago, IL

Chicago sits on a flat glacial lake plain where wet snow, ice dams and freeze-thaw cycles hammer every roof edge, chimney and skylight from November through March. On the brick bungalows of the Bungalow Belt, the two-flats of Logan Square and Bridgeport, and the steep gables of Beverly, the first place water finds a way in is almost always the flashing. Flashing, Chimney & Skylight Repair in Chicago is the work we do most in winter and early spring: we bend, fit and seal the metal that keeps water out of the joints your roof cannot cover on its own. We fabricate flashing in-house so every chimney cricket, valley and curb fits the way it should, not the way a stock piece almost does. If you are already chasing a stain on the ceiling, start with our metal roof leak repair page and we will trace it to the source. Licensed and insured, working across Chicago and the surrounding suburbs.

Why flashing and chimney leaks dominate Chicago roofs after a hard winter

Chicago roofs take a specific beating: heavy wet snow sits on low-pitched hip roofs, melts at the warm brick chimney, refreezes at the eave and drives water sideways under anything that is not properly stepped and sealed. Add hail, derecho wind and falling elm and maple limbs, and the flashing at the chimney, skylight curb, dormer and valley is the first thing to fail. On greystones and Georgian townhomes in Lincoln Park, parapet wall flashing is the usual culprit. On 1990s and newer subdivision homes in Naperville and Schaumburg, it is often the skylight curb and the valley metal that were never detailed for our snow loads.

• Chimney flashing pulls away from brick as mortar spalls and the counterflashing loses its seal.
• Skylight curbs crack at the sealant joint and let meltwater track along the frame into the deck.
• Valley metal rusts through on older roofs and backs water up under the shingles or panels.
• Step flashing lifts after freeze-thaw cycles and wind-driven rain gets behind the wall.
• Parapet and counterflashing on flat-roof commercial and brick buildings separates from the masonry wall.

Every one of these is a small, targeted repair when we catch it early, and a deck replacement when we do not.

Key info: On a brick two-flat in Bridgeport last February, a homeowner had paid twice to reseal a skylight from the inside. The real problem was a cracked curb flashing pan that had been letting water run down the rafter for two seasons. We rebuilt the curb flashing in 20 oz copper and stopped the leak for good.

Roofing permits and inspection requirements vary by jurisdiction across Cook County and the collar counties. Always confirm the current rules with your local building department before work starts. The City of Chicago Department of Buildings publishes its permit information at chicago.gov.

How we trace and repair flashing, chimney and skylight leaks in Chicago

We do not guess and we do not smear sealant over a failed joint. We get on the roof, find where the water actually enters, and rebuild the flashing so it sheds water the way the detail was designed to. On a low-slope bungalow roof, that often means pulling back the panels or shingles at the chimney, inspecting the deck, and replacing the step and counterflashing rather than patching it. Our crews work in Chicago weather year-round and know what a proper ice-and-water detail looks like under our snow loads.

1. We inspect the roof, chimney, skylight curb, valleys and parapet walls and photograph every suspect joint.
2. We water-test the likely entry points when the leak is not obvious from below.
3. We remove the failed flashing and check the deck and underlayment for rot or saturated sheathing.
4. We fabricate new flashing in-house, in copper, painted steel or lead, to fit the actual dimensions on your roof.
5. We install it with proper step, counter and pan detailing, seal the terminations and re-secure the surrounding panels.
6. We test again and walk you through what we found and what we replaced.

If the leak is coming through the roof field rather than a penetration, our metal roof repair service covers panel and fastener issues, and our copper and specialty metal page covers the custom work on bays and turrets.

Key info: A Queen Anne in Oak Park had a turret that leaked every spring. The original copper valley had been patched with tar three times. We removed the tar, formed a new soldered copper valley to match the turret radius, and the ceiling has stayed dry through two melt seasons since.

Flashing repair methods we use on Chicago roofs

The right approach depends on the roof type, the penetration and how much of the surrounding assembly has failed. Here is how we match the method to the job.

We choose the method after we see the roof, not before, and we tell you why one approach fits your building better than another.

Flashing, Chimney & Skylight Repair cost in Chicago: what to expect

Most flashing repairs start at $600 and go up from there depending on access, height and how much of the assembly has failed. A straightforward chimney re-flash on a one-story bungalow is very different from a turret valley rebuild on a three-story Queen Anne. We give you a written scope and a firm number before we start. For a broader look at how we price work, see our pricing overview.

• Roof height and pitch affect labor and setup time, especially on steep gables and turrets.
• Access matters: a chimney on a flat roof is faster than one tucked behind a dormer or a tight gangway.
• Material choice drives cost, with painted steel at the low end and copper or lead at the high end.
• Hidden rot in the deck or sheathing adds carpentry once we open the flashing.
• Emergency or winter work carries a premium because of safety and weather constraints.

Getting two or three estimates is smart on any flashing job, and it is the best way to compare scope, not just price.

What to look for when hiring a metal roofing contractor near me in Chicago

Flashing work is detail work, and the contractor you hire matters more than the material. Ask for proof of licensing and insurance, get at least two or three written estimates, and ask for references from jobs similar to yours. Confirm who pulls the permit and whether your building sits in a historic district or under HOA design review, since both can restrict materials and profiles. A contractor who cannot answer those questions clearly is not the one you want on your roof.

To set up a free estimate, reach us through our contact page or call (872) 242-4810.

Flashing, Chimney & Skylight Repair in Chicago: Pricing Guide

Indicative pricing, the exact cost depends on square footage, finish, and site access. Free personalized estimate within 24h at (872) 242-4810.