In Cicero We Fix What Can Be Fixed First
Cicero is brick, block after block of it, packed tight from Cermak down to 35th and out past Central. A lot of those roofs do not need to be torn off yet. They need somebody to climb up, tell the owner the truth about what is actually failing, and put a real number on it. That is how we work this town.

Brown architectural shingle over brick and stucco
Wall To Wall Brick, And Two Roof Systems Per House
Cicero built out early and it built dense. Most of the town went up between the 1900s and the 1940s for the workers at Hawthorne Works and the shops along the rail lines, so the housing stock here is a century old and nearly all masonry. Chicago-style brick bungalows with hipped roofs, two-flats with flat decks and parapets, frame cottages that got a brick veneer somewhere along the way, and long rows where the gangway between two buildings is barely wide enough to swing a ladder.
What makes Cicero different from the suburbs south of here is that one building often carries two completely different roofs. The front of a bungalow is pitched and shingled. The back kitchen addition, the sunroom or the dormer shed is low slope, covered in rolled asphalt or an old built-up system somebody mopped down in the eighties. Those two systems meet at a flashing, and that flashing is where a huge share of Cicero leaks start. A roofer who only does shingles will patch the pitched side and hand you a bill while the real failure sits four feet away on the flat.
Density adds its own problems. When buildings share a gangway three feet wide, the water off two roofs lands in one narrow strip, and a downspout that dumps at the foundation there has nowhere to go but into a basement. Party walls and shared parapets mean a neighbor’s neglected coping can leak into your unit. We look at the whole water path on a Cicero building, including what the building next door is doing to yours.
The Work Cicero Calls For Most
- Shingle roof repair on bungalow hips and gables where wind stripped tabs off one slope and the rest of the roof still has life in it.
- Flat roof repair on rear additions, porches and two-flat decks, which is the most common call we get in this town.
- Shingle roof replacement when the mat is spent, done as a full tear-off so we can see the century-old decking underneath.
- Gutter replacement and downspout rerouting where a narrow gangway is drowning a foundation.
- Wind damage repair after the straight-line gusts that come off the prairie and run east down Ogden and Cermak.
- Townhome roof repair and small multi-unit work for owners who rent out the second floor or the coach house.
We also get called by the small commercial buildings that share these blocks. The storefronts on Cermak and 22nd, the corner taverns, the auto shops and the little industrial buildings near the rail corridor all sit under flat roofs. Those get handled through commercial roof leak work and full commercial flat roof systems, scheduled so the business stays open.
Repair-First Triage, Because Budgets Are Real
Plenty of the people who call us from Cicero are working families who bought a two-flat, live downstairs, rent upstairs and put every spare dollar into keeping the building sound. Selling those owners a full tear-off when a section repair will hold six or eight more years is not a business we want to be in.
So we go up and actually look, not squint from the ground. We check whether the shingle mat still has flex or has gone brittle and shedding granules. We check whether the flat section is failing at the seams and the flashings, which is repairable, or whether the membrane is saturated and the deck is soft, which is not. Then we tell you which of three things you are looking at: a repair that buys real years, a partial replacement of the section that is done, or a full tear-off.
When it is the third one, we do not soften it. Angelo helps owners get pre-approved for financing when a building needs more roof than one paycheck covers, and we will phase work across sections when phasing makes sense structurally. What we will not do is put a new roof over a bad deck to hit a number.
What A Hundred-Year-Old Deck Looks Like
When we tear off in Cicero we expect to find things. Board sheathing with gaps instead of plywood, which is normal for the era and fine as long as the boards are sound. Old knob-and-tube runs stapled to rafters. Two or three previous roofs where somebody overlaid instead of tearing off. Chimneys abandoned when the house went to forced air and never capped.
We price the job knowing this. Deck replacement gets quoted as a per-sheet or per-board number up front, so if we open the roof and find rot, you already know what it costs and you approved it before we started. Nobody gets an ugly phone call at noon on tear-off day with the roof open and a new price attached.
Weather On This Side Of The County
Cicero gets the same Chicago winter as the city it borders. Snow sits on the flat sections, melts off the warm parts of the deck, and refreezes at the cold parapet edge. Ice dams form on the bungalow hips over poorly ventilated attics. In summer, the storms that track east along the Eisenhower drop hail and straight-line wind, and a hundred-year-old brittle shingle mat does not survive either one well.
After any hail or high wind, get the roof looked at within a couple weeks even if nothing is dripping. Bruised shingles do not leak in July. They leak in February when the freeze finds the soft spot. We inspect and photograph the way an adjuster needs, and if the damage is not worth filing, we say that and leave you the photos. More on the insurance claims page.
The Company Behind The Truck
Guardian Roofing Systems is second generation. Angelo Ristich learned this trade under his father Frank, took the company over in 2013, and still runs the jobs himself. In Cicero that matters because the person who quotes your roof is the person who will be standing on it. We use satellite measurements to give you a straight price fast on the phone.
A+ with the BBB, HomeAdvisor Elite Service award, licensed and insured in Illinois. The gallery shows the work itself: tear-offs down to bare deck, flat sections rebuilt, new shingle over old brick. Ask and we will give you a nearby address to drive past.

Underlayment down at the peak, deck inspected
Cicero At A Glance
Century-old brick bungalows, two-flats and cottages. Mixed pitched and flat roofs on the same building. Tight gangways, shared parapets, real budgets.
Mon to Sat, 9 to 5. Emergency patching when a roof opens up. Deck repair priced before we tear off.
(312) 590-4853Cicero And The Blocks Around It
Cicero sits on the city line, which puts it in the middle of our Cook County run. Chicago begins at the eastern border and brings the same two-flats and flat-roof work our crews do here. Head south on Cicero Avenue and you are in Oak Lawn and then our shop in Alsip. A storm that runs the Eisenhower corridor hits Cicero and the West Side in the same twenty minutes, so the crew that tarped a building on Austin Boulevard in the morning is often on a Cicero roof by afternoon. The whole coverage map lives on the service areas page.
Cicero Roofing Questions
Can you actually repair my roof instead of replacing it?
Often yes, and that is where we start. If the shingle mat still has flex and the failure is localized at a flashing or a valley, a repair buys real years. We only call for a tear-off when the mat is spent or the deck is going.
My bungalow has a flat roof over the back kitchen. Who handles that?
We do, in the same visit as the pitched section. That transition is the single most common leak point on a Cicero bungalow, and splitting it between a shingle guy and a flat roof guy means nobody owns the flashing between them. One crew, one quote, one warranty.
What happens if you find rotten wood after the tear-off starts?
You already know the price. We quote deck repair per board or per sheet before the job starts, so we show you photos, you approve the count, and the number was set in advance. No mid-job renegotiation.
The gangway between me and my neighbor floods every storm. Is that a roof problem?
Usually a gutter and downspout problem made worse by two roofs draining into three feet of space. Rerouting a downspout and upsizing the run fixes most of it. We check the whole water path, and gutter installation is part of what we do.
I own a two-flat and rent the top unit. Can you work with tenants in place?
Yes. We schedule access, keep the gangway and parked cars protected, and give you notice you can pass along upstairs. More on the multi-family roofing page.
Can I spread the work out over a couple of seasons?
Sometimes, if the sections are independent enough that phasing does not create a bad seam. Angelo also helps owners get pre-approved for financing so a needed roof does not sit another winter.
Get A Straight Answer On Your Cicero Roof
Call Guardian Roofing, say what the roof is doing and how old the building is, and get a real number without a sales visit first. Or send the address through the contact page for a same-day callback.