How Much Does a New Roof Cost in Chicago?
Ask five roofers what a new roof costs and you’ll get five different answers, and most of them will be guesses, because none of them have been on your roof yet. Two houses a few miles apart can need completely different jobs. Think of a brick bungalow on the Northwest Side and a 1990s colonial in Schaumburg, or a Victorian in Oak Park and a three-flat in Bridgeport. Neither owner is getting overcharged. The price is just built from different pieces. We work all over Chicago and Northeastern Illinois, so this is how we’d explain those pieces if you were standing in the driveway with us, and how we handle the money so cost doesn’t talk you out of fixing a roof that needs it.
Why We Won’t Quote a Roof Over the Phone
We get asked for a ballpark on the very first call all the time, and we get why. But a number from someone who hasn’t looked at your roof is a guess, and guesses turn into change orders. So every estimate starts with us getting up there, counting what’s on the roof, and checking what’s under it. You get a written scope of work before anything begins, and the price in that scope is the price you pay. No surprise fees halfway through.
What Moves the Price
Pitch and Roof Type
Start with the shape of the house. A steep roof on a bungalow in Jefferson Park or Portage Park is a different job than a flat roof on a Logan Square two-flat, and both are different from the big, steep, cut-up roofs on newer homes in Schaumburg and Naperville. Steeper roofs take more labor and more safety setup. Flat and low-slope roofs get systems like modified bitumen or rubber EPDM, and they have to meet energy code, including continuous insulation, which adds material and detail work.
People tend to assume a flat roof should cost less because there’s less to it. It usually doesn’t. Water doesn’t run off a flat roof the way it runs off a pitched one, so the seams, flashing, drainage and insulation all have to be right. Get one of those wrong and you’re looking at a leak, or a failed inspection.
How Many Layers Are Already Up There
This is the one that catches people off guard. A lot of older homes in Oak Park, Berwyn and the bungalow neighborhoods in the city have been re-roofed two or three times, with each new roof going right over the last one. Code limits how many layers can stay, so at some point everything has to come down to the deck. More layers means more tear-off, more hauling and more labor. We check the layer count at the start, so you hear about it during the consultation and not on day one of the job.
What’s Under the Old Roof
Nobody can see the decking until the old roof is off. After a few decades of freezing and thawing, ice dams and the occasional slow leak, some of those boards end up soft or rotted. Our crews look as they tear off, and we replace what’s bad so the new roof sits on something solid. Nobody likes hearing there’s more work under the roof, but putting new shingles over rotted wood just means paying for the same roof twice.
Material
Asphalt shingles cost the least to put on, and they usually need replacing again in 15 to 20 years. Metal costs more up front and can last two to three times as long. The metal systems we install are independently tested for wind uplift, water penetration, structural load and freeze-thaw cycling, which matters when summers hit 95 and winters can hit 15 below. Tile can go 50 years or more, though concrete tile can have a harder time with Chicago’s freeze-thaw cycles over the long haul. Tile is a product our family has a personal connection to, so we’re always happy to talk it through.
If you’re planning to stay in the house, whether that’s in Evanston, Park Ridge or Schaumburg, add up what the roof costs over its whole life and not just the first invoice. The cheapest roof to install is often not the cheapest one to own.
Permits, Access and Weather
Working in and around a big city has its own costs. Permits take real time, and every town has its own rules, so what Chicago wants isn’t necessarily what Oak Park or Schaumburg will ask for. We handle the permit paperwork, including Express Permits in the city where they apply, so you never end up on hold with a building department.
Access matters too. A lot in Lakeview or Wicker Park, with a neighbor a few feet away on each side and a narrow alley out back, takes more planning to protect the property and get the debris out. And because roofs around here take lakefront wind and winter ice dams, what goes under the shingles matters a lot: ice and water shield, synthetic underlayment, drip edges and flashing. You’ll never see any of it again once the roof is finished, and it’s usually the difference between a roof that leaks in year three and one that doesn’t leak for decades.
Who You’re Dealing With
Castello is a family business. We’ve been at this for 25 years, and we recently made it official by incorporating, which is a funny thing to say about a company that’s been working for a quarter century. Francisco Duarte runs it, and we’re licensed in Illinois under #104.020912. We work out of Lincoln Park and take jobs across Chicago, out to Winnetka, Highland Park, Barrington, Hinsdale and Naperville, and everywhere in between. We’re growing, with Rockford next and Champaign after that.
It matters who’s standing behind your roof. Most of what we offer, the zero deposit, the lifetime warranty, the ten years of annual inspections, only makes sense if you plan on still being around in ten years. We are.
How We Handle the Money
A new roof shouldn’t wipe out your savings, and how a contractor asks to get paid tells you a lot about them. We don’t ask for a deposit. Not a dollar before the crew shows up. If a roofer wants a big chunk of cash before a single shingle has come off, ask them why.
We also offer flexible financing with monthly payments, so you can get the whole project done with as little out of pocket as possible. The estimate is clear from the start. And once the roof is on, it’s backed by a lifetime warranty on whatever system goes on your house, and we come back every year for 10 years to inspect it for free.
That last part changes how you should think about price. A roof that comes with a lifetime warranty and ten years of inspections is a different product than one where the relationship ends when the truck pulls away.
What to Expect When You Call Us
It starts with a free consultation. We look at the roof, count the layers, and talk through what makes sense for your house and your budget, whether that’s shingles, metal, tile or a flat roof system. You get the scope in writing, with the price, before anything starts. If you want financing, we set that up then too, and there’s still no deposit.
Once you say go, we take care of the permits. On the day, the crew tarps off your landscaping and walkways before anything comes down, takes the old roof off, and checks the decking. Anything rotted gets replaced. Then the layers nobody sees go on, and then the roof itself. When the crew is done, we run a magnetic sweep over the yard, the driveway and the alley, so a stray nail doesn’t end up in a tire. After that you’ve got the lifetime warranty, and we’re back every year for 10 years to look at the roof again.
What It Looks Like for Different Homeowners
- The bungalow owner on the Northwest Side calls about a patch and finds out there are three layers up there. That means a full tear-off and a bigger number than they expected. It’s a bummer, but it’s much better to hear it in a consultation, with the scope in writing, than in the middle of the job.
- The two-flat or three-flat owner in the city is paying for a system built to handle water on a roof that barely slopes, plus the insulation standards that come with it. Zero deposit and monthly payments help a lot here, since these are bigger jobs.
- An Oak Park homeowner with an older house may be dealing with several layers, some deck repair and a roofline with more angles than a newer home. If your house is in a historic district, tell us up front, because some towns have extra review for exterior changes.
- A Schaumburg homeowner with a newer house is usually looking at a big, steep roof and a shingle job that’s reached that 15 to 20 year mark. The size of the roof drives the number there. If you’re staying put, it’s worth asking about metal.
- Anyone with a sudden leak, whether it came from a storm or from a home inspector flagging the roof before a sale, doesn’t have time to save up. That’s what 0% deposit and monthly payments are for.
The Short Answer
What does a roof cost in Chicago and the suburbs around it? It depends on your pitch, your layers, your decking, your material and the town you’re in. What shouldn’t be a mystery is how the number gets built or how you pay for it. Look for an estimate that explains itself, with permits handled, a clear scope of work, no deposit, financing that fits your budget, and a warranty and maintenance plan that last longer than the job does.
Want a real number for your own roof? Call us and we can discuss your project.