It is the first question almost everybody asks, and it is a fair one. The trouble is that "what does a roof cost" is a bit like "what does a car cost" — the honest answer is a range so wide it is nearly useless until someone has actually looked at your building.
So instead of inventing a number, here is what genuinely moves the price on a Chicago roof. Once you understand these, you can read any estimate you are handed and tell whether it is complete.
1. Size — Measured in Squares, Not Square Feet
Roofers price in squares. One square is 100 square feet of roof surface. A typical Chicago bungalow might be 15–20 squares; a large suburban two-storey could be 35–45. Note that roof area is always larger than the footprint of the house, because of pitch and overhangs.
2. Pitch and Complexity
A simple gable roof that two people can walk on is the cheapest thing to replace. Cost rises with:
- Steepness. Past about 7/12 pitch, crews need staging and harnesses, and everything slows down.
- Number of planes. Every valley, hip, dormer and intersection is extra labour and extra flashing.
- Penetrations. Chimneys, skylights, vent stacks, bathroom fans — each one has to be flashed correctly.
- Access. A Chicago lot with a three-foot gangway and no alley access is a very different job from a suburban house with a driveway you can back a dumpster onto.
3. Material
| Material | Relative cost | Realistic life in Chicago |
|---|---|---|
| Three-tab asphalt shingle | Lowest | 15–20 years |
| Architectural asphalt shingle | Low–moderate | 25–30 years |
| Modified bitumen (flat) | Moderate | 15–25 years |
| EPDM / TPO (flat) | Moderate | 20–30 years |
| Cedar shake | High | 30–40 years with maintenance |
| Standing seam metal | Highest | 40–70 years |
The gap between three-tab and architectural shingle is much smaller than the gap in performance, particularly with lake wind. We recommend architectural on nearly every house.
4. How Many Layers Come Off
Illinois generally permits two layers of shingle. If you have two up there, both come off, and that is roughly double the tear-off labour and double the disposal. Many Chicago homes have had a layover done at some point, and the homeowner has no idea until we start.
5. Deck Condition — The Real Variable
This is the one nobody can price accurately in advance, and any estimate that pretends otherwise is not being straight with you. Until the old roofing is off, nobody knows what the plywood or board sheathing underneath looks like. If there have been long-running leaks or years of ice damming, sections will be soft and will need replacing.
A good estimate handles this transparently: a per-sheet price for replacement decking, stated upfront, so if we find rot you already know what it costs and there is no argument on site. Be wary of any bid that does not mention decking at all.
6. The Things Cheap Bids Leave Out
When one estimate is dramatically lower than the others, it is usually because something is missing. Check for:
- Ice & water shield at eaves and valleys. Non-negotiable in Chicago, and one of the first things omitted to win a bid.
- New flashing. Reusing old chimney and wall flashing saves money and guarantees a leak within a few years.
- Drip edge. Cheap, required, frequently skipped.
- Ventilation work. A new roof over an unventilated attic ages twice as fast.
- Permits. Roofing work in Chicago generally requires one, and pulling it costs money and time.
- Debris removal and disposal. Ours is always included, but confirm it in writing on any bid.
- Gutter removal and reinstallation if they come off for the tear-off.
7. Flat Roofs Are Priced Differently
If you own a Chicago two-flat, three-flat or a bungalow with a flat rear section, part of your roof is a completely different system. Flat roofing is priced on membrane type, insulation, and — critically — whether the drainage needs correcting with tapered insulation. There is also often masonry work at the parapet, which is a separate trade that we happen to also do.
How to Compare Estimates Properly
- Get three, and get them in writing and itemised.
- Compare line by line, not bottom line to bottom line.
- Confirm each one includes ice & water shield, new flashing, drip edge, permits and disposal.
- Ask what the per-sheet decking replacement price is.
- Ask for the licence number and proof of insurance, and verify them.
- Ask what the workmanship warranty is and get it in writing.
Get a Real Number
We will come out, get on the roof, look in the attic, photograph what we find and give you an itemised written estimate — free, with no obligation. If your roof has years left in it, we will tell you that instead.
Frequently Asked Questions
We can talk through the variables, but we will not pretend to price a roof we have not seen. Too much depends on pitch, access, layers and deck condition. The inspection and written estimate are free, so there is no reason to guess.
No — but a dramatically cheaper one is almost always leaving something out. Compare the line items rather than the totals and you will usually find where the difference is.
We accept cash, checks, and debit and credit cards. Talk to us about payment scheduling when we quote — we work with homeowners on staging payments against project milestones.
Insurance covers sudden accidental damage — wind, hail, a fallen tree. It does not cover a roof that has simply reached the end of its life. If you think you have storm damage, get it inspected and documented promptly.
Talk to a real roofer
Free estimates across Chicago and a 100-mile radius. Call (773) 418-2040 or request a quote online.
