Skyline RoofingBridgeport, Chicago
Menu
Call(312) 555-0126
Chicago skyline at sunrise, seen from the South Side

Flat roofs and bungalow roofs,
built for a Chicago winter.

Skyline Roofing has worked on two-flats, three-flats, bungalows and greystones from Bridgeport out to Hyde Park since 2010. Modified bitumen and TPO on the flat roofs, architectural shingle on the pitched ones, and the city permit filed before the first tear-off.

(312) 555-0126

Illinois Roofing License #104.017205 (Unlimited). Licensed, bonded and insured. Certificate of insurance sent with every written estimate.

3500 S Halsted St, Chicago, IL 60609. Owner Dana Okafor, crew of eight.

Request a written estimate

Roofs on Chicago buildings

Most of the roofs on the South Side fall into four building types, and each one needs different work. Here is what we do on each, in plain terms. Every job gets a written, itemized estimate the same week we look at the roof.

Two-flat and three-flat

Flat roof, usually two or three layers of old built-up roofing under whatever was patched on last. We tear off to the deck, replace rotted decking, then install two-ply modified bitumen (torch-down or self-adhered) or a 60 mil TPO membrane. New scuppers, gutters and downspouts where the old ones have rusted through.
Typical scopeTear-off, deck repair, insulation board, two-ply mod bit or TPO, scuppers, parapet flashing. Two to four days.

Bungalow

Pitched hip roof, often with a low-slope rear addition or dormer. Full tear-off, ice and water shield six feet up the eaves and in every valley, synthetic underlayment, and architectural shingle (GAF Timberline HDZ or Owens Corning Duration). The low-slope section gets modified bitumen, not shingle, because shingle leaks under a 2:12 pitch.
Typical scopeTear-off, ice and water shield, underlayment, architectural shingle, ridge vent, rear mod bit section. One to two days.

Greystone

Flat roof behind a limestone or brick parapet. The roof is only half the job. Parapet walls, coping stones and chimneys are where most greystone leaks start, so we coordinate tuckpointing and coping repair with a licensed mason we have worked with for years, and sequence it so the new membrane is never cut for masonry work afterward.
Typical scopeMod bit or TPO, counterflashing into the parapet, coping repair with the mason, chimney cricket. Three to five days including masonry.

Courtyard building

Large flat roof, internal drains, and a condo board or landlord who needs numbers in writing. We walk the roof with the board, mark every drain, curb and penetration on a roof plan, and price the job in sections so it can be phased across two budget years if it has to be.
Typical scopeTPO or mod bit in phases, drain rebuilds, roof deck framing where the board wants one, skylight replacement. One to three weeks.
Also: porch roofs, roof decks, skylights, scuppers, and emergency tarping. Ask about your building
Roofer working on the roof of a brick townhouse
Three-flat reroof, Pilsen, April 2026
Close view of finished roofing on a pitched roof
Bungalow, McKinley Park
Chicago skyline over rooftops
The view from a Bronzeville roof deck

City permits, handled by us

Every roof replacement in Chicago needs a permit from the Department of Buildings, and the inspector can show up during the job. A lot of roofers skip it, and the fine lands on the building owner, not the roofer. We do not skip it. Dana files the permit, pays the fee as a line on your estimate, posts it on site, and meets the inspector when they come.

Most straightforward reroofs go through the city's Easy Permit Process and come back in a few days. Roof decks, new skylights, and any structural repair to the deck need a standard permit with drawings, which takes longer, and we tell you that up front so the schedule is honest.

  • Permit filingFiled under our license, posted on site, closed out after final inspection.
  • Dumpster and streetDumpster permit and any curb-lane closure pulled through the city, not left to you.
  • Insurance workIf a hail or wind claim is involved, we provide the itemized scope and photos your adjuster asks for. We do not handle the claim itself.
  • Landmark districtsBuildings in a landmark district get a review before we order material, so nothing gets pulled off later.

The permit number is printed on your invoice. If a future buyer or the city asks, it is on record.

Dana Okafor, owner of Skyline Roofing, on a job site

Dana Okafor, owner since 2010

I grew up in a two-flat on Lowe Avenue and spent my twenties on roofing crews all over the South Side before starting Skyline Roofing in 2010. We are eight people. I still walk every roof myself before we quote it, and I am on site the day of tear-off, because that is the day you find out what is really under the old roof.

You get one written estimate, itemized by material and labor, within the week. If we open the roof and find rotted decking, you get a photo and a per-sheet price before we replace it, not a surprise on the invoice. We clean up with magnets and a walk-around every day, because this is a neighborhood with kids and dogs on the sidewalk.

Dana OkaforOwner, Skyline Roofing. Illinois Roofing License #104.017205 (Unlimited).

2010Founded in Bridgeport
8Full-time crew, no day labor
Same weekWritten estimate delivered

What owners on the South Side say

Read all reviews on Google
Marisol R.PilsenMarch 2026Google
They pulled the permit before I even asked. Our three-flat had three layers of old roof and two other companies wanted to go over it. Dana tore it off, replaced eleven sheets of decking and sent me a photo of each one, and the mod bit roof has been dry through two storms. Done in three days.
Kevin O.BridgeportMay 2026Google
Bungalow reroof, one day, exactly the price on the estimate. Crew showed up at 7, shingles were on by 4, and the rear addition got a proper flat roof instead of shingle like the last guy did. My gutters were cleaner when they left than when they came.
Denise W.BronzevilleJuly 2026Google
Our greystone parapet was the real problem and Dana was the only one who said so. Skyline coordinated the mason, redid the coping, and then put the TPO roof on with the flashing tied into the new brick. The condo board got a roof plan with every drain marked. No leaks since.

Where we work

We stay close to the shop on Halsted so a crew can be on your roof within a day of a leak call. If your building is on the South Side or near West Side and not on this list, call anyway, we probably know the block.

  • BridgeportHome base, 3500 S Halsted St
  • PilsenThree-flats and storefront roofs
  • McKinley ParkBungalows and two-flats
  • BronzevilleGreystones and courtyard buildings
  • Hyde ParkCondo boards and larger flats
  • Back of the YardsTwo-flats and porch roofs

Shop at 3500 S Halsted St. Estimates within about six miles of here, Monday to Saturday.

Request a written estimate

Fill in the five fields and Dana will call you back the same business day to set a time to walk the roof. Or skip the form and call (312) 555-0126.

Active leak? Call. We tarp the same day and put the tarp cost toward the repair.

Skyline Roofing
3500 S Halsted St
Chicago, IL 60609
(312) 555-0126
Monday to Saturday, 7am to 6pm
Illinois Roofing License #104.017205 (Unlimited)
We call back the same business day. No mailing list, no text blasts.
Call (312) 555-0126