Can You Replace Windows in Winter? Chicago & Milwaukee Guide

Mr. Roof & Remodeling installer replacing a second-story window, one opening at a time
November 12, 2026

Most homeowners assume window replacement has to wait until spring. In Chicagoland and Southeast Wisconsin, that often means living through another winter with drafty, foggy or frozen-shut windows. The good news: windows can be replaced in winter, and for many homes it is one of the smartest times to do it.

At Mr. Roof & Remodeling we replace windows all year long, including the coldest months in Chicago and Milwaukee. Here is how winter installation works, what to expect, and when it makes sense to wait.

Yes, you can replace windows in winter

The biggest worry we hear is simple: “Won’t my house get freezing cold?” It doesn’t have to. The key is how the work is organized.

We replace windows one opening at a time. The old window comes out, the new one goes in, it is insulated and sealed, and only then do we move to the next opening. Each opening is exposed for a short time, so the rest of the house stays warm. We also keep the work area closed off as much as possible and clean up as we go.

Modern installation materials are made for cold weather too. Low-expansion insulating foams and sealants are available for cold-weather application, so a January install can seal just as tight as a June install when it is done right.

Why winter can be a good time to replace windows

You can see exactly which windows are failing

Winter shows the problems clearly: cold drafts by the frame, frost or ice on the inside of the glass, condensation between the panes, and windows that won’t open or lock. When you replace in winter, you fix the windows you know are costing you money right now.

You save on heating sooner

Heating is the biggest energy cost for most homes in Illinois and Wisconsin. Replacing old, leaky windows before the worst of the season means you start feeling the difference this winter, not next one.

Easier scheduling

Spring and summer are the busiest months for exterior work. In winter it is usually easier to find an installation date that fits your schedule.

What winter window replacement looks like, step by step

  1. Free in-home estimate. We measure every opening and talk through styles, glass options and budget. You can also visit our office at 529 N Wolf Rd in Wheeling to see products in person.
  2. Ordering. Windows are made to measure for your openings. We install Home Guard and Marvin windows, and Power European windows and doors for homeowners who want a European-style product.
  3. Installation day. We protect floors and furniture, then replace one opening at a time: remove, install, insulate, seal, trim.
  4. Clean-up and walkthrough. Old windows are hauled away. We check that every window opens, closes and locks properly before we leave.
Mr. Roof & Remodeling installer sealing new double-hung replacement windows
Every new window is insulated and sealed before we move to the next opening.

Which windows to choose for a Midwest winter

For cold climates, look at the whole window, not just the price:

  • Double or triple-pane glass with low-E coatings to keep heat inside.
  • Warm-edge spacers that reduce condensation and frost at the edge of the glass.
  • Good weatherstripping and a tight-locking sash, especially on double-hung and slider windows.
  • Window style that fits the room. Casement and awning windows seal tightly when closed; picture windows don’t open at all and are very efficient.

Not sure which style fits your home? See our replacement windows page for double-hung, slider, picture, casement and awning options.

When it is better to wait

Winter installation works for most homes, but sometimes we recommend a different plan:

  • During extreme cold snaps or heavy snowstorms we may move the date a few days for the safety of the crew and your home.
  • Large openings that need structural changes, like turning a window into a patio door, may be better planned for milder weather.
  • If exterior paint or stucco work is part of the job, that part may need to wait until temperatures allow.

We will tell you honestly during the estimate if your project should wait.

Vacation homes and seasonal properties

Own a lake house in Lake Geneva or a seasonal home in Wisconsin? Winter is often when these homes sit empty, which makes it a convenient time to replace windows. We work on vacation homes with the owner off site and keep you updated during the project.

Financing available

New windows are an investment. We offer financing options, so you don’t have to wait for spring to fix drafty windows. Ask about financing during your free estimate.

Frequently asked questions

Will my house get cold during installation?

Only one opening is open at a time and only briefly. Most homeowners notice very little temperature change in the rest of the house.

Do you repair old windows?

No. We specialize in full window and door replacement, not repairs.

Which areas do you serve?

We serve Chicago and the northwest and north suburbs, including Wheeling, Arlington Heights, Palatine, Mount Prospect, Glenview, Des Plaines and Northbrook, plus Southeast Wisconsin: Milwaukee, West Allis, Brookfield, Kenosha, Racine and Lake Geneva. See all our service areas.

Get a free window estimate this winter

Tired of drafts and frost on the glass? Call (877) 408-5405 or request a free quote online. Mr. Roof & Remodeling has been a family-owned company since 2011.

Leave a Reply

Your email address will not be published. Required fields are marked *