Exterior painting Chicago
Exterior painting built for Chicago weather
Industrial-grade prep and professional coatings designed for Chicago winters. Licensed contractor since 2003. Free estimate.
Exterior painting services
Exterior painting that survives Chicago winters
Chicago weather is brutal on exterior paint. Freezing winters, road salt, spring humidity, and summer heat cause paint to crack, peel, and fade far faster than in milder climates. We use the same prep and coating standards as industrial contractors — applied to your residential property with residential-grade care and precision.
For metal porches, fire escapes, and wrought iron fences, see our specialized metal porch and fence refinishing service which uses industrial aliphatic urethane coatings built for Chicago climate.
Services we offer
- Complete exterior repaints
- Trim, fascia & soffit painting
- Porch floors & ceilings
- Masonry & brick painting
- Garage doors & service doors
- Fence painting & wood staining
- Metal porch & fence refinishing
- Two-flats, three-flats & multi-unit buildings
Our exterior painting process
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1. In-person estimate
We assess your home exterior in detail — peeling areas, bare wood, caulking failures, moisture damage, and anything needing repair before paint is applied. -
2. Power washing
We power wash all surfaces to remove dirt, mildew, chalking, and loose paint. This step is not optional — painting over contaminated surfaces is the fastest way to failure. -
3. Surface prep & caulking
We scrape loose paint, sand rough edges, fill cracks, replace damaged caulking around windows and doors, and address any wood rot before priming. -
4. Professional primer
All bare wood and repaired areas get a professional exterior primer coat. Skipping primer is one of the most common shortcuts — we never do it. -
5. Premium exterior coatings
We apply Sherwin-Williams Duration, Benjamin Moore Aura Exterior, and other professional-grade coatings engineered for Chicago climate conditions.
“We received outstanding service on two home painting jobs. Kamil repaired our bathroom ceiling expertly and repainted a wall that had water damage. And he did a fine job repainting the rear of our home. Windy City Painters will always be our first call.”
— Chicago homeowner, West Town — Yelp Review
Frequently asked questions
When is the best time for exterior painting in Chicago?
Late spring through early fall, May through September. We need temperatures consistently above 50 degrees with low humidity for proper adhesion and curing.
How long does exterior paint last in Chicago?
A properly prepared and painted exterior should last 7 to 10 years. Our work is backed by a workmanship warranty.
Can you paint brick exteriors?
Yes. We have extensive experience painting brick, masonry, and concrete block common in Chicago vintage housing stock. We use masonry-specific primers and breathable coatings.
Do you repair wood rot before painting?
Yes. Painting over wood rot is a waste of money. We identify and address rotted wood, damaged siding, and deteriorated caulking before any paint is applied.
Do you paint two-flats and multi-unit buildings?
Yes. We regularly work on Chicago two-flats, three-flats, and small multi-unit buildings, coordinating with tenants and working around occupancy schedules.
Do you offer a warranty?
Yes. If paint peels or fails prematurely due to our application, we return and make it right at no charge.
Free estimate
In-home consultation — no obligation
Exterior painting
Interior painting
Exterior painting
Cabinet refinishing
Wallpaper installation
Drywall repair
Wrought iron / porch
Multiple services
✓ Thank you! We will contact you within one business day.
Mon–Sat 7:30am – 6pm
📍 Windy City Painters
2101 W Rice St
Chicago, IL 60622
Serving all Chicago neighborhoods
Why choose us
Why Chicago homeowners choose Windy City Painters
Meticulous preparation
We repair cracks, sand surfaces, fill holes, and prime before painting. This is what makes a finish last 8 to 10 years instead of 2 to 3.
Respectful of your home
Furniture protected, floors covered, daily cleanup. We work quietly and leave your space spotless every single day.
Transparent pricing
You receive a detailed written estimate upfront — no surprises, no hidden charges, no upsells mid-project.
Premium materials only
We use Sherwin-Williams Emerald and Benjamin Moore Aura — the best available — on every project.
Other services