Drawing-painting Events in Chicago

Check out happening drawing-painting events all around Chicago, IL

Gold Coast Art Fair (68th annual)

 Sat, 20 Jun at 10:00 am Grant Park

Black Boy Art Show Chicago

 Sun, 24 May at 03:00 pm 754 E Grand Ave USD 50 to 66

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

 Sat, 28 Feb Studio W.I.P. USD 62

Moonlit Wave - Paint and Sip in Chicago | Classpop!™

 Sat, 11 Apr at 07:30 pm Pinot's Palette - Logan Square USD 56

Sip and Paint at 360 CHICAGO

Tue, 14 Apr at 07:00 pm 360 CHICAGO

Under the Moonlight - Paint and Sip in Chicago | Classpop!™

 Fri, 10 Apr at 08:00 pm Pinot's Palette - Logan Square USD 56

Van Gogh Les Iris - Paint and Sip in Chicago | Classpop!™

 Sat, 11 Apr at 03:00 pm Pinot's Palette - Logan Square USD 56

Birch Grove at Sunset - Paint and Sip in Chicago | Classpop!™

 Wed, 08 Apr at 07:30 pm Pinot's Palette - Logan Square USD 32

Monet's Chicago Twilight - Paint and Sip in Chicago | Classpop!™

 Fri, 24 Apr at 08:00 pm Pinot's Palette - Logan Square USD 56

Monet’s Water Lilies II - Paint and Sip in Chicago | Classpop!™

 Sat, 18 Apr Pinot's Palette - Logan Square USD 56

Art Battle Chicago - April 10, 2026

 Fri, 10 Apr at 07:00 pm SPIN Chicago USD 20 to 29

Simply Starry Night "Your City" - Paint and Sip in Chicago | Classpop!™

 Fri, 08 May at 08:00 pm Pinot's Palette - Logan Square USD 56

Galaxy Beach - Paint and Sip in Chicago | Classpop!™

 Sat, 16 May at 07:30 pm Pinot's Palette - Logan Square USD 56

Colorful Chicago - Paint and Sip in Chicago | Classpop!™

 Wed, 20 May at 07:00 pm Pinot's Palette - Logan Square USD 49

Northern Night Lights - Paint and Sip in Chicago | Classpop!™

 Fri, 22 May at 07:30 pm Pinot's Palette - Logan Square USD 56

Sunset Waterfall - Paint and Sip in Chicago | Classpop!™

 Thu, 09 Apr at 07:30 pm Pinot's Palette - Logan Square USD 49

Eventide - Paint and Sip in Chicago | Classpop!™

 Sat, 04 Apr at 07:30 pm Pinot's Palette - Logan Square USD 56

Your City Night Glow - Paint and Sip in Chicago | Classpop!™

 Sun, 05 Apr at 05:00 pm Pinot's Palette - Logan Square USD 56

Waterlilies, Monet Style - Paint and Sip in Chicago | Classpop!™

 Sun, 12 Apr at 05:00 pm Pinot's Palette - Logan Square USD 56

Spring Waterfall - Paint and Sip in Chicago | Classpop!™

 Wed, 22 Apr at 07:00 pm Pinot's Palette - Logan Square USD 49

Cubist Portrait - Paint and Sip in Chicago | Classpop!™

 Thu, 23 Apr at 07:30 pm Pinot's Palette - Logan Square USD 49

Misty Mountain Galaxy - Paint and Sip in Chicago | Classpop!™

 Sat, 25 Apr at 07:30 pm Pinot's Palette - Logan Square USD 56

My Happiest Hour - Paint and Sip in Chicago | Classpop!™

 Sun, 26 Apr at 01:00 pm Pinot's Palette - Logan Square USD 56

Glowing Starry Night - Chicago - Paint and Sip in Chicago | Classpop!™

 Thu, 23 Apr at 07:00 pm Pinot's Palette - Logan Square USD 49

Goldentide - Paint and Sip in Chicago | Classpop!™

 Sun, 26 Apr at 05:00 pm Pinot's Palette - Logan Square USD 56

Blossom Moon River - Paint and Sip in Chicago | Classpop!™

 Wed, 29 Apr at 07:00 pm Pinot's Palette - Logan Square USD 49

Green Forest Falls - Paint and Sip in Chicago | Classpop!™

 Fri, 01 May at 08:00 pm Pinot's Palette - Logan Square USD 56

Moon Over the Pines - Paint and Sip in Chicago | Classpop!™

 Sat, 02 May at 07:30 pm Pinot's Palette - Logan Square USD 56

Moon Glow Forest - Paint and Sip in Chicago | Classpop!™

 Sun, 03 May at 05:00 pm Pinot's Palette - Logan Square USD 56

Van Gogh's Blue Vase - Paint and Sip in Chicago | Classpop!™

 Sat, 04 Apr Pinot's Palette - Logan Square USD 56

Japanese Rising Sun - Paint and Sip in Chicago | Classpop!™

 Wed, 29 Apr at 07:30 pm Pinot's Palette - Logan Square USD 32

Bridgeport Art Center Third Friday Open Studios APRIL 2026

 Fri, 17 Apr at 07:00 pm Bridgeport Art Center Chicago Free

R&B Night Paint & Sip

 Sat, 18 Apr at 07:30 pm Lux Accents Studios USD 60 to 90

Emotional Support Animals by Nicole J. Georges with Jessica Hopper

 Thu, 30 Apr at 07:00 pm Women & Children First Free

Titanic Sip and Paint

 Sat, 11 Apr at 07:00 pm Toast To Paint USD 34 to 45

18+ Sober Opossum Paint & Sip

 Sat, 28 Feb at 06:00 pm The Insect Asylum USD 32 to 96

Open Paint Night Fridays

 Fri, 03 Apr at 06:00 pm Studio15 / TVP Tech Solutions LLC USD 34

BYOB Paint & Sip: Tropical Moon Glow

 Sat, 11 Apr at 07:30 pm Lux Accents Studios USD 61

Paint Your Date BYOB Paint & Sip

 Sat, 17 Jan at 06:00 pm Art City USD 55

Family Painting Event - "Bee Happy" (Open to Adults and Kids 6+)

 Sun, 12 Apr at 12:00 pm Sip & Paint USD 39

Art & Matcha: Faux Stained Glass & Japanese Matcha Tasting

 Sat, 04 Apr at 04:00 pm 5420 W Belmont Ave USD 59

April Showers - A Sip and Paint at Eris Brewery

 Wed, 22 Apr at 06:30 pm ERIS Brewery and Cider House USD 31

Tote Bag Paint Event

 Sat, 16 May at 01:00 pm Millennium Park USD 29

Date Night Photography Class - Chicago - Photography Class by Classpop!™

 Sun, 29 Mar Digital Photo Academy Chicago USD 426

R&Bling Thursdays- Sip, Paint, Bling (BYOB)

 Thu, 09 Apr at 06:30 pm Ka'Lab: The Creative Space USD 50 to 269

Paint your Own Permanent Flowers: A Paper Mâché Floral Workshop

 Thu, 23 Apr at 06:30 pm Design at 329 USD 104

Get Lit: Art of the Cocktail

 Tue, 12 May at 05:30 pm American Writers Museum

The NCS Chicago Cartoon Cabaret

 Sun, 12 Apr at 05:00 pm Chief O'Neill's Pub - Upstairs Room Free

May Flowers Sip & Paint Night at Eris Brewery!

 Wed, 20 May at 06:30 pm ERIS Brewery and Cider House USD 31

Build Your Dream Garden with Young Cultural Stewards

 Sat, 09 May at 11:00 am Jane Addams Hull-House Museum Free

Acrylic Landscape Painting

 Thu, 16 Apr at 07:00 pm AponteART Gallery USD 45

Kids Easter Sunday Instructed Art Class

 Sun, 05 Apr at 12:00 pm Toast To Paint USD 34

Paint & Sip

 Fri, 24 Apr at 07:00 pm RLM Studio Free

Community Canvas Autism Awareness Event

 Sat, 25 Apr at 02:00 pm Legler Regional Library, Chicago Public Library Free

Art City Open Studios

 Fri, 27 Mar at 06:00 pm Art City USD 28

Lincoln Park Zoo

 Sat, 20 Jun at 12:00 pm Lincoln Park Zoo

Your Photo, Your Painting - Paint and Sip in Chicago | Classpop!™

 Fri, 20 Mar KaLab USD 46

Artisan Painted Bread Sip n' Paint + Baking Class

 Sat, 04 Apr Bettie's Chicago USD 125

Spring Fling Paint n Sip Workshop

 Sat, 18 Apr at 06:00 pm Studio15 / TVP Tech Solutions LLC USD 55 to 87

Opossum Paint Party for Kids ages 5-17

 Sun, 22 Feb at 04:30 pm The Insect Asylum USD 32 to 73

Figure Drawing Bootcamp

 Wed, 04 Mar at 06:30 pm Art City USD 108

SKETCH / BOOK

 Mon, 30 Mar at 06:00 pm Quimby's Bookstore USD 45

BYOB Paint & Sip: Floral Boots

 Sun, 19 Apr at 02:30 pm Lux Accents Studios USD 61

Collage Workshops with Paloma Trecka

 Sun, 19 Apr at 01:00 pm Oleander & Artesian USD 55 to 87

Chicago Paint ,Play And Picnic Experience

 Fri, 08 May at 08:00 am 337 E Randolph St Free

Pilsen Spring Sketchwalk

Sat, 16 May at 09:00 am Pilsen, Chicago, Illinois

Intro to Figure Drawing Course

 Sun, 26 Apr at 12:00 pm LMN Wedge Studio & Gallery USD 77 to 258

QCDC Project Windows Abstract Art Creative Experience

 Fri, 01 May at 03:00 pm Ka'Lab: The Creative Space Free

Sunday Funday Art Day

 Sun, 07 Dec at 10:00 am 5420 W Belmont Ave USD 8 to 43

Draw Now! Sunday Art Workshop

 Sun, 01 Feb at 06:00 pm Art City USD 55

Ink Blot Workshop with Catriona MacLeod

 Wed, 15 Apr at 01:00 pm Regenstein Library Free

Story Makers: Write, Illustrate, and Bind your own Book

 Fri, 10 Jul at 09:00 am The WasteShed USD 215

Faux Stained Glass Art Class BYOB

 Mon, 16 Feb at 03:00 pm LMN Wedge Studio & Gallery USD 50

Free Street's Open Hours: Arts & Healing

 Tue, 10 Feb at 06:00 pm 4625 S Ashland Ave Free

FREE PAINTING / SCULPTURE WORKSHOP!!!!

 Sat, 09 May at 01:00 pm Forum 301 Free

Selena Paint Party

 Fri, 23 Jan at 07:00 pm 5420 W Belmont Ave USD 31

Things in Jars: Botanical Inks

 Thu, 20 Aug at 06:00 pm South Chicago Farm USD 13 to 109

Little Pieces, Big Picture: Family Mosaic Art Making Experience.

 Sat, 07 Feb at 12:00 pm KaLab Bronzeville USD 104

DIY Faux Stained Glass

 Fri, 01 Aug at 02:00 pm 5420 W Belmont Ave USD 23 to 55

Drop-In Figure Drawing

 Sat, 17 Jan at 11:00 am Art City USD 23

Wednesday Figure Drawing Session with Live Model

 Wed, 28 May at 06:00 pm 1579 N Milwaukee Ave suite 206 USD 26 to 174

Thursday Art Night

 Thu, 12 Feb at 07:00 pm Eli Tea Bar Free

Painting Pottery

 Thu, 02 Oct at 12:00 pm 5127 N Clark St USD 30

Floral Watercolor Workshop

 Tue, 26 Aug at 02:00 pm 5420 W Belmont Ave USD 29 to 34

Painting on Pottery

 Tue, 05 Aug at 02:00 pm 5420 W Belmont Ave USD 0 to 29

Art City BYOB Paint & Sip

 Tue, 10 Feb at 01:00 pm Art City USD 50

Cacti Watercolor Workshop

 Mon, 17 Nov at 12:00 pm 5420 W Belmont Ave USD 26