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

Exterior Painting · Based in Highland Park

Exterior house painting across Chicagoland

Curb appeal that weathers the seasons. Siding, trim, decks and brick, prepped down to the surface and coated to stand up to sun, wind and freeze. Family owned, based in Highland Park, working across the North Shore and Chicagoland.

The Prep

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

Exterior painting in Highland Park and across the North Shore starts with the weather, because it's hard on a home. Sun fades paint, freeze and thaw lift it, and moisture gets 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 true and the surface sound for years.

We protect your landscaping, work around your home and your days, and clean the work area at the end of each day.

What We Paint

Every surface outside, prepped to last

Siding & Full Exterior Repaint
01

Siding & Full Exterior Repaint

Cedar clapboard and shakes, vinyl and aluminum siding, LP, and fiber cement, washed, primed, and coated in a finish that holds its color through Chicagoland summers and winters.

Decks, Fences & Railings
02

Decks, Fences & Railings

Decks, fences, pergolas, and railings, cleaned, sanded, and stained or painted to shed water and weather.

Deck staining and painting
Trim, Doors & Garage Doors
03

Trim, Doors & Garage Doors

Fascia, soffits, shutters, front door painting, and garage doors, clean lines and a hard, weather-ready finish.

Trim and door painting
Brick & Masonry
04

Brick & Masonry

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

North Shore Homes

Exterior painting near the lake

Cedar siding and shakes, limestone and brick, deep eaves and original wood trim: the North Shore's older homes were built with materials that reward proper prep and punish shortcuts. Lake wind and moisture, and the freeze and thaw of a Chicago winter, find every gap in a bad seal, so the wash, scrape, sand, caulk and prime sequence is most of the job.

We work in Highland Park, Highwood, Lake Forest, Lake Bluff, Glencoe, Winnetka and across the North Shore, and travel throughout Chicagoland for the right project. See the areas we serve.

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 cut the lines clean and lay the coats even.

Every project includes a free color consultation with our experts.

How We Work

What to expect

01

Free Estimate

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

02

Prep & Protection

We mask and cover floors, furniture and nearby surfaces before any coating goes on.

03

Expert Application

Finish coats applied by our own crew.

04

Final Walkthrough

We inspect the finished work with you and clean the work area before we leave.

Why Gallagher

Built to hold up outside

A Gallagher quotes the work and is on site through it.

Request a Free Estimate
  • Family owned, with our own crew

    A Gallagher quotes your project and stays across it. The crew doing the work is ours.

  • 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.

  • Fixed estimates

    A written quote with the surfaces, the prep and the number of coats in it, and a weather plan if the season is tight.

Recent Exteriors

Recent exteriors

Exterior Repaint
Full Exterior
Exterior Repaint

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. 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. How long depends on the surface, the preparation, the coating, how exposed that side of the house is and how it is maintained. Preparation is the part we control, 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.

Can I just paint over old exterior paint?

Sound paint can usually be recoated once the surface is clean and prepared. What will not hold is a finish over chalky, peeling or bare spots, so those need dealing with first. We wash, scrape loose paint, sand, caulk and prime, so the new finish bonds and the weather stays out.

Beautifully painted Chicagoland home

Let's Begin

Tell us about your project

We will come out, look at the work with you, and send a written estimate with the scope set out. There is no charge and no obligation.