Two-story Chicagoland home with freshly painted gray siding, crisp white trim, and a stone facade

Exterior Painting · Chicagoland

Curb appeal that weathers the seasons

Siding, trim, decks, and brick, prepped down to the surface and coated to stand up to Chicagoland sun, wind, and freeze. Family owned, based in Highland Park, serving the North Shore and greater Chicagoland.

The Prep

It is not the paint that lasts. It is the prep.

The Chicago metro's weather is hard on a house. Sun fades, freeze and thaw lift, moisture creeps in behind a bad seal. So we wash, scrape, sand, caulk, and prime before a finish coat ever goes on. That groundwork is what keeps the color crisp and the surface sound for years.

We protect your landscaping, work around your home and your days, and leave the place cleaner than we found it. A repaint should make the house feel new, not put your life on hold.

What We Paint

Every surface outside, prepped to last

Siding & Full Exterior Repaint
01

Siding & Full Exterior Repaint

Clapboard, shakes, LP, and fiber cement, washed, primed, and coated in a finish that holds its color through Chicagoland summers and winters. The whole house, brought back to new.

Trim, Doors & Garage Doors
03

Trim, Doors & Garage Doors

Fascia, soffits, shutters, front doors, and garage doors, crisp lines and a hard, weather-ready finish. The details that set your curb appeal apart.

Decks, Fences & Railings
02

Decks, Fences & Railings

Decks, fences, pergolas, and railings, stripped, sanded, and stained or painted to shed water and weather. The outdoor wood you actually touch, protected.

Brick & Masonry
04

Brick & Masonry

Brick, stucco, and masonry painted or stained with breathable, made-for-masonry coatings, so the finish lasts and the surface still breathes.

Kind Words

Trusted by neighbors across Chicagoland

Color, Considered

It all begins with the right color

From timeless neutrals to a bold front door, our color experts help you choose an exterior palette that fits your home and your street, then apply it with a craftsman's hand.

Every project includes a free color consultation with our experts.

How We Work

From the first call to the final walkthrough

01

Free Estimate

We walk your home, listen to your vision, and give you a clear, honest quote.

02

Prep & Protection

We mask, cover, and protect everything before a single brush is lifted.

03

Expert Application

Premium finishes applied with care, by the family and our trusted crew.

04

Final Walkthrough

We review every detail together and leave your home cleaner than we found it.

Why Gallagher

Built to hold up outside

We are a family business in the truest sense. The care we bring to the outside of your home is the care we would give our own.

Request a Free Estimate
  • The same family, start to finish

    The people who quote your project are the people on the ladders. Your name is on the door, and ours is on the work.

  • Prep that protects

    We wash, scrape, sand, caulk, and prime, so the finish bonds tight and Chicagoland weather stays out.

  • Weather-ready finishes

    We work in Benjamin Moore and Sherwin-Williams exterior lines, matched to your siding and our climate.

  • Honest, fixed estimates

    A clear written quote with no surprises, and no pressure to say yes.

Recent Exteriors

Homes we have had the honor to refresh

Exterior Repaint, Lake Forest
Exterior Repaint, Lake Forest
Full Exterior, North Shore
Full Exterior, North Shore
Exterior Repaint, Naperville
Exterior Repaint, Naperville

Good to Know

Exterior painting, answered

Still wondering about something? We are happy to talk it through.

630-300-3071
How much does it cost to paint a house exterior?

It is priced by the size of the home, the surfaces involved, the prep and repairs needed, and the number of stories. After a walkthrough we send a detailed, fixed estimate with no surprises. Estimates are always free.

When is the best time to paint outside in the Chicago metro?

Roughly spring through fall, when temperatures and humidity cooperate. We watch the forecast and schedule around it, because paint applied in the wrong conditions will not last.

How long will an exterior repaint last?

With proper prep and premium paint, many years. Prep is what decides it, which is why we wash, scrape, sand, caulk, and prime before a finish coat ever goes on.

Do you pressure wash and prep first?

Yes. We power wash, scrape loose paint, sand, caulk gaps, and prime bare spots. On an exterior, that prep is most of the job and all of the difference.

Can you paint or stain my deck and fence?

Yes. We strip, sand, and stain or paint decks, fences, pergolas, and railings so they shed water and stand up to the seasons.

Do you offer free estimates?

Yes. Every estimate is free and pressure free. We walk the exterior, talk through colors, and send a written quote you can take your time with.

Beautifully painted Chicagoland home

Let's Begin

Ready for a home you are proud to come back to?

Tell us about your project and we will come out for a free, in-home visit and a clear, detailed estimate. No pressure, just honest guidance from a family that cares.