Do I REALLY Need to Replace Skylights With My New Pitched Roof?

If you’re planning a roof replacement in Chicago and you have skylights, you’ve probably asked yourself: Do I really need to replace them too? The short answer — especially if your skylights are over 10 years old — is yes, it’s strongly recommended.

Keeping old, out‑of‑warranty skylights while installing a brand‑new roof is like putting worn‑out tires on a new car. It may work for a while, but you’re setting yourself up for leaks, costly roof repairs, and frustration down the line. At Anchor Point Roofing, we’ve seen this scenario play out more times than we care to count — particularly in older Chicago homes where weather and roof age combine to accelerate wear.

Why You Should Replace Skylights With Your Roof

➤ 1. Older Skylights Are Prone to Failure

Skylights have seals, flashings, and components that break down over time. Once they reach around 10–15+ years old, the chances of leakage, condensation between panes, drafts, and energy inefficiency rise significantly. A failing skylight can quickly turn into a source of water intrusion — meaning more repairs or interior damage.

➤ 2. Cost & Warranty Benefits

When you replace your skylights during a roof replacement project, you only pay for one mobilization, one set of labor costs, and one warranty period. Roofers can install new skylights and flashing correctly while the roof deck is exposed, which is much more cost‑efficient than doing it separately later.

Trying to save money now by keeping old skylights can be a false economy. If they start leaking later, you might pay twice — once for repairs and once for the eventual replacement. And if the new roof has to be disturbed again to fix leaks, you risk damage to your own new investment.

➤ 3. Protect Your New Roof From Damage

Re‑flashing an old skylight after a roof replacement often voids manufacturer warranties on roofing and skylight products. Worse, if water starts leaking around the old units, the roofer may have to tear up new shingles to fix the issue — defeating the purpose of quality roof repairs or replacement.

Signs Your Skylights Are Already Failing

If any of these sound familiar, it’s another good reason to replace your skylights with your roof:

Water stains or leaks near the skylight

Condensation or fogging between glass panes

Drafts or energy loss around the unit

Cracked, cloudy, or damaged glass

Final Thoughts — It Depends on Your Needs

Ultimately, whether you must replace your skylights depends on your goals, budget, and the condition of your current units. But if you want:

✔ A new, watertight roof system

✔ Fewer future repairs

✔ Better energy efficiency

✔ Peak performance and warranty coverage

…then replacing old skylights during your pitched roof replacement is the smart move.

📹 For more insight, check out our video on skylight replacement:

https://youtu.be/12EA9DZFja0?si=EHicXAGTf6POOhOJ

Location: Chicago, IL