★★★★★ Rated by Chicago homeowners $50 OFF when you book your job online Free estimates · (708) 815-7720
★★★★★ Painting Chicago exteriors since 2018

Siding Painting Service in Chicago, IL

Wood, vinyl, aluminum and hardboard siding painted to last through Chicago winters. Power washed, scraped, primed, and two coats applied. Licensed and insured, with the price in writing before we start.

📍 Serving Chicago, IL and all Cook County suburbs
Licensed & insured in Illinois Free written estimates Homes from $1,800
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Quick Answer

Quick Answer

Siding painting in Chicago starts around $1,800 for an average home, with pricing based on square footage, siding type and condition. A typical two-story house runs between $2,500 and $4,500. That price comes from Vanguard Painting, a licensed and insured company based in Melrose Park. Every job includes power washing, scraping loose paint, sanding rough spots, priming bare areas, two finish coats and full cleanup around the house. We paint wood, vinyl, hardboard and aluminum siding across Chicago and all of Cook County.

Average home from$1,800
Two-story house$2,500
Timeline3–6 days
EstimateFree
Power washEvery siding job starts with a full wash to remove dirt and mildew
Scrape and sandLoose paint removed, rough edges sanded smooth before priming
FreeWritten estimate with the price locked before we start
Two coatsAlways two finish coats. One thick coat never holds up
On every job

What You Get When We Paint Your Siding

Book exterior siding painting in Chicago and this is the package. No corners cut on prep, no water-based paint over oil without primer.

Power washing

Full exterior wash with detergent to remove dirt, mildew, pollen and chalked paint residue.

Scraping and sanding

All loose and peeling paint scraped off. Edges feathered smooth with sandpaper.

Caulking gaps

Window trim, corner boards and siding seams caulked where water can get behind.

Primer where needed

Bare wood, repaired sections and drastic color changes get a primer coat first.

Two finish coats

Proper dry time between coats. This is where durability and even color come from.

Brush and roll, not just spray

We back-roll sprayed paint so it works into the siding instead of just sitting on top.

Windows and trim masked

Glass, trim and doors covered so no overspray lands where it shouldn't.

Site cleanup

Every scrap of paint, every drop sheet and all debris hauled off your property.

Real numbers

Siding Painting Prices in Chicago

Here's where our pricing starts on the siding jobs Chicago homeowners ask about most. Siding type, square footage, and how much prep work is needed move the final number. You get that number in writing first.

Single-story homeWood, vinyl or hardboard siding, full prep and two coats$1,800
Two-story homeFull house, including gables and soffits. More ladder work.$2,500
Brick and siding comboHouse with brick lower and siding upper. Both surfaces prepped separately.$2,800
Exterior painting packageSiding, trim, doors and gutters painted in one schedule.$3,200
Deck and siding togetherSiding painted and deck stained. Combine jobs for better scheduling.$2,200
Trim and fascia onlySoffits, fascia, window trim and corner boards painted separately.$800
Commercial building sidingRetail, office and multi-unit building exterior sidingQuoted

Not sure which of these you need? Call (708) 815-7720. Most Chicago siding jobs get priced over the phone in about five minutes.

Local knowledge

Chicago Siding Has Its Own Wear Patterns

Chicago's weather swings from humid summers to lake-effect winters. That beats up siding. Wood swells, vinyl gets brittle, and paint fails at the south and west exposures first.

South and west take the hit

Sun and heat break down paint on the south and west sides of Chicago homes faster. We give those walls extra attention on prep and apply primer on bare spots first.

Vinyl needs special primer

Vinyl siding can't be painted with standard house paint. We use bonding primer made for plastic and flexible topcoats that move with the vinyl.

Old wood laps

Pre-war Chicago homes have real wood siding. It's beautiful but absorbs moisture. We work when weather is dry and use oil-based primer on bare spots. This is standard on our exterior painting work.

Homes built before 1978 can carry lead paint under the top layers. Our crews follow RRP lead-safe practices on those, which is one more reason to choose a licensed company.

Estimate to walkthrough

How We Paint the Siding on a Chicago Home

Eight steps, same order every time, whether it's a brick bungalow with wood trim or a two-story frame house in Jefferson Park.

1

Walk and inspect

We check every wall, test paint adhesion, note rotted boards and write the price down before we leave.

2

Power wash

Full exterior wash with detergent. Dirt, mildew and chalked paint rinsed off.

3

Scrape loose paint

Any peeling or bubbling paint scraped off. Surface feathered smooth.

4

Sand and caulk

Rough spots sanded. Gaps around windows and corners caulked.

5

Prime bare spots

Raw wood, repairs and color transitions get a primer coat.

6

First coat

Full first coat applied. We brush and back-roll for adhesion.

7

Second coat

Second coat once the first has dried. Even color, full coverage.

8

Cleanup and walkthrough

Drop sheets picked up, site swept, and we walk the perimeter with you.

Where we are541 Winston Dr Suite 1, Melrose Park, IL 60160
Chicago drive timeVaries by neighborhood
Siding types

The Siding Work Chicago Calls Us For

Most calls fall into one of three categories. Same crew and same prep standard on all of them, different material requirements.

Wood siding painting in Chicago, IL

Wood siding and clapboard

Old-growth pine, cedar and HardiePlank. We prime bare spots with oil-based primer and topcoat with 100% acrylic. This is the core of our exterior painting service.

WoodClapboardHardie
Vinyl siding painting in Chicago, IL

Vinyl and aluminum

Vinyl needs a primer designed for plastic. Aluminum needs oxidation removed. We handle both with specific products.

VinylAluminumBonding primer
Commercial siding painting near Chicago, IL

Commercial and multi-unit

Apartment buildings, storefronts and offices with large siding areas. We work around business hours. Also see commercial painting.

CommercialMulti-unitInvoiced
Who shows up

A Crew That Knows Chicago Siding

Our shop is at 541 Winston Dr in Melrose Park. We work Chicago neighborhoods every day and know what the weather does to the east side versus the south side. The person who prices your job is the person who paints it. Same crew from estimate to cleanup.

Exterior work is all about timing and prep. We watch the forecast, schedule for dry stretches, and protect your landscaping before we start. We do not rush a siding job. Rushed prep fails before two winters pass.

Plenty of Chicago customers book brick painting or deck staining once we're already on the property.

Get my free estimate
Vanguard Painting siding crew in Chicago, IL
Sound familiar

What Goes Wrong With Siding Paint, and What You End Up With

Almost every Chicago siding call opens with one of these failures. Here's the cause on the left, and here's the result when we pack up.

The problem

Paint peeling after one winter

Rushed prep or painting over chalky old paint. The new coat doesn't bond, and by spring it's flaking off.

Blistering on the south side

Heat builds up under a topcoat that wasn't primed. Moisture trapped behind the paint pushes it off.

Caulk cracking at the joints

Cheap caulk or no caulk at the gaps. Water gets behind and rots the wood under the paint.

What you get

Paint that holds through a Chicago winter

Surface fully prepped, primer on every bare spot, two coats of 100% acrylic. It handles the freeze-thaw cycle.

Even coverage on all four sides

South and west walls get the same prep as the north side. No weak spots.

Water stays out

Every gap and seam caulked before paint goes on. No rot, no water stains inside.

True on every Chicago siding painting we take:

Free written estimate, price locked before we start
Licensed and insured in Illinois
Power washed, scraped, sanded, primed and two topcoats
Landscaping covered and protected
Full cleanup, no paint chips or debris left
Stuck on colors? Book a color consultation before we start.
📞 Booking siding painting now. Call (708) 815-7720 and we'll price your Chicago exterior in about five minutes.
Finished work

What the Exterior Looks Like When We Leave

Smooth, even color, no drips on the trim, no paint on the windows.

Siding painting before and after in Chicago, IL
Wood siding scraped, primed and painted
Vinyl siding painted in Chicago, IL
Vinyl siding with bonding primer and topcoat
Exterior siding painting completed in Chicago, IL
Full exterior repaint, trim and siding
Neighbors talking

What Chicago Customers Say After the Last Coat

Most of our Chicago siding work comes from people who had a bad paint job before. Read what they said about the prep, the finish and how the house looked when we cleared out.

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Also handled

Other Exterior Work We Do Around Chicago

Siding painting is a big part of our schedule, but the same crew handles everything outside.

Brick painting

Masonry paint on Chicago brick. See brick painting.

Deck staining

Decks and fences stained or sealed. See deck and fence staining.

Garage painting

Detached garages and sheds. See garage painting.

Interior painting

Inside work while we're there. See interior painting.

Need work across the county? We cover the whole Cook County service area, and everything we do in the city sits on the Chicago painting page.

Quick answers

Siding Painting in Chicago, IL: Common Questions

How much does siding painting cost in Chicago, IL?
Siding painting in Chicago starts around $1,800 for a single-story home, or $2,500+ for a two-story house. Estimates are free and written down first.
How long does it take to paint siding in Chicago?
Most Chicago siding jobs take three to six days, depending on weather and size. Prep, two coats and cleanup all included.
Can you paint vinyl siding?
Yes. Vinyl needs a bonding primer made for plastic. We use that before the topcoat so paint sticks and moves with the vinyl.
Do you power wash before painting?
Yes. Every siding job starts with a power wash. Dirt, mildew and chalked paint have to come off or the new paint won't hold.
Do you paint aluminum siding?
Yes. Aluminum needs the oxidation removed first. We prep it properly so paint bonds and doesn't peel.
Do you paint commercial buildings?
Yes. Retail, office and multi-unit buildings with siding are covered in our commercial painting work.
Do you protect landscaping during painting?
Yes. Shrubs, flower beds and walkways are covered with drop cloths. Paint drips and overspray don't reach your plants.
Is Vanguard Painting licensed and insured?
Yes, licensed and insured in Illinois, based at 541 Winston Dr in Melrose Park. Call (708) 815-7720 for a free estimate and $50 off.
Ready when you are

Get Your Chicago Siding Painted Right

Free estimate, a real written price, licensed and insured, and a crew that knows Chicago exteriors. Book online and take $50 off.

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