Top-rated painters.

Get matched with top painters in Winnetka, IL

Enter your zip and get matched with up to 3 pros

Matching on HomeAdvisor

Share some details icon
Share some details about your home project.
Match with local pros icon
Within moments, match with highly-rated local pros.
Compare quotes icon
Compare quotes and choose the best pro for the job.

Find Painters in Winnetka

Avatar for Sefner Painting
Sefner Painting
4.9(
127
)

Serving Winnetka, IL and surrounding areas

Approved

In business since 2004

Free estimates

Credit card accepted

"Third time I've hired Greg Sefner for painting work in my apartment. Excellent work on original, 100+ year old plaster walls and ceilings patching, painting, and addressing wallpaper bubbling off walls."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+10

Response time1 day
1 neighbors recently requested a quote
Recommended by97%of homeowners
Avatar for CHICAGO PAINTERS INC
CHICAGO PAINTERS INC
4.8(
93
)

Serving Winnetka, IL and surrounding areas

Approved

In business since 2001

Free estimates

Warranties offered

"All painting completed to our satisfaction and exceeded expectations! Matched existing color, fixed all blemishes, and only quoted and painted what was necessary."
Beautiful wallpaper work in Niles, 60714
Beautiful wallpaper work in Niles, 60714
Check out this top notch work in Roscoe Village area in Chicago. 
Paint used is Sherwin Williams Pure White SW7005.
Call us today to get a refreshed look in your home!
Check out this top notch work in Roscoe Village area in Chicago. 
Paint used is Sherwin Williams Pure White SW7005.
Call us today to get a refreshed look in your home!
What a beautiful job using Sherwin Williams Super paint Velvet

+47

Response time6 hrs
1 neighbors recently requested a quote
Recommended by90%of homeowners
Avatar for MQ Painting
MQ Painting
4.9(
87
)

Serving Winnetka, IL and surrounding areas

Approved

In business since 2003

Free estimates

Emergency services offered

"Awesome experience; Jose was very responsive and showed us a lot of paint samples until we got exactly what we wanted. Showed up on time and finished early. His crew was hard working and very careful of not damaging anything. Cleaned up everything too. Will definitely use them again."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+3

Response time8 hrs
Recommended by100%of homeowners
Avatar for VD Painting, Inc.
VD Painting, Inc.
5.0(
18
)

Serving Winnetka, IL and surrounding areas

Approved

In business since 2014

Free estimates

Emergency services offered

"VD Painting did it all! They were so easy to work with. Quite and clean. I could not have asked to be matched with a better company. They do more than paint too!! It was an amazing experience for my first time hiring painters for a job that was simply to big for me. Thank You, VD Painting!"
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+98

5 neighbors recently requested a quote
Recommended by100%of homeowners
Avatar for Ocegueda Painting Corp
Ocegueda Painting Corp
5.0(
22
)

Serving Winnetka, IL and surrounding areas

Approved

Super Service Award Winner

Free estimates

Emergency services offered

Warranties offered

"Mr Ocegueda was very pleasant and hard working. We booked him last Fall so he could do Spring painting for us. We have already asked him to patch and paint our living room. We were very pleased with his work and would highly recommend him."
Exterior Painting Project
Exterior Painting Project
After painting wood
Interior Painting Project
Interior Painting Project

+52

Response time2 days
1 neighbors recently requested a quote
Recommended by86%of homeowners
Avatar for Lilian Touch Restoration Inc
Lilian Touch Restoration Inc
4.9(
60
)

Serving Winnetka, IL and surrounding areas

Approved

Super Service Award Winner

In business since 2019

Free estimates

Emergency services offered

"very professional guy no problem he painted everything like requested over 2500 sq ft entire house . paint job was excellent A+ I would hire a Raphael the owner and use him again and his Lilian Touch Restoration inc company for any paint job i do recommended him from my end to all others to try and use him ."
Painting - Exterior Project
Painting - Exterior Project
Painting - Exterior Project
Painting - Exterior Project
Painting - Interior Project

+437

6 neighbors recently requested a quote
Recommended by87%of homeowners
Avatar for Big League Painting
Big League Painting
4.7(
101
)

Serving Winnetka, IL and surrounding areas

Approved

In business since 2015

Free estimates

Warranties offered

"We have a very old house….this company was first class and beyond skilled and thorough. VERY HIGHLY recommend you hire them for your next painting job"
Lake Forest Home
New Railing
Deck
Crew Chief
2126 Harrison Street

+9

Response time11 hrs
Response rate92%
5 neighbors recently requested a quote
Avatar for Bici Brothers Drywall & Painting
Bici Brothers Drywall & Painting
5.0(
21
)

Serving Winnetka, IL and surrounding areas

Approved

Super Service Award Winner

In business since 2010

Free estimates

Emergency services offered

"Bici Brothers did an amazing job. They painted the interior of my entire house(3500 sq ft). Job was completed on time and on budget. Very professional, even did work without instruction to make the project really stand out. I will use them again for my next project."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
1 neighbors recently requested a quote
Recommended by80%of homeowners
...
Showing 1-10 of 1172

FAQs for painting projects in Winnetka, IL

Most homeowners opt for semi-gloss or high-gloss paint to make the baseboards stand out against the walls. If you’d rather keep things subtle, matching the wall sheen with eggshell or satin also works well. When your trim has nicks or dents, reach for a flatter, matte finish—it hides minor imperfections better than a shiny coat.

Stripping old paint from trim costs $1 to $3 per linear foot. Pros use specialized tools and techniques to lift away existing layers without gouging the wood, then prep the surface for a fresh finish. While it adds to your budget, proper removal protects the molding and sets the stage for a smoother, longer-lasting paint job.

Tackling the baseboards first often leads to crisper lines. Painting trim first lets you tape off the boards instead of the walls, so you’re less likely to splatter color where you don’t want it. Any stray marks on the wall get covered when you roll on the final coat, making the whole process faster and tidier.

You can absolutely paint baseboards in place. Leaving them installed avoids the risk of cracking or misaligning the boards when they’re reattached. With thorough cleaning, light sanding, and careful taping, a pro—or an experienced DIYer—can achieve a sharp, factory-smooth finish while saving you the hassle of prying off and reinstalling trim.

Painting almost always beats replacement in cost. Swapping out baseboards runs about $150 in DIY materials or roughly $1,100 with a pro, while repainting costs about $50 in supplies and $1 to $5 per square foot for labor. Unless the boards are warped or severely damaged, a fresh coat delivers the same visual upgrade for a fraction of the price.

Paintable caulk and wood filler are the go-to fixes for nail holes in baseboards. Wood filler sands flush for a glass-smooth surface, while caulk provides a flexible seal that won’t crack as the house settles. Either way, patching those tiny divots before you prime ensures your finished baseboards look seamless.

The Winnetka, IL homeowners’ guide to painting services

From average costs to expert advice, get all the answers you need to get your job done.