Drawing-painting Events in Chicago
Check out happening drawing-painting events all around Chicago, IL
C2E2 2026 Live Cosplay Model Drawing
Fri, 27 Mar at 11:00 am
C2E2 At McCormick Place
Grotesque Burlesque @ C2E2 2026 – Live Cosplay Figure Drawing
Fri, 27 Mar at 11:00 am
C2E2
Black Boy Art Show Chicago
Sun, 24 May at 03:00 pm
754 E Grand Ave
USD 50 to 66
Gold Coast Art Fair (68th annual)
Sat, 20 Jun at 10:00 am
Grant Park
Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™
Sat, 28 Feb
Studio W.I.P.
USD 62
Simply A Starry Night - Paint and Sip in Chicago | Classpop!™
Sat, 14 Mar at 07:30 pm
Pinot's Palette - Logan Square
USD 56
Simply A Starry Night - Paint and Sip in Chicago | Classpop!™
Wed, 18 Mar at 07:30 pm
Pinot's Palette - Logan Square
USD 32
Galaxy Beach - Paint and Sip in Chicago | Classpop!™
Sun, 15 Mar at 05:00 pm
Pinot's Palette - Logan Square
USD 56
Moonlit Wave - Paint and Sip in Chicago | Classpop!™
Sat, 11 Apr at 07:30 pm
Pinot's Palette - Logan Square
USD 56
Japanese Rising Sun - Paint and Sip in Chicago | Classpop!™
Sun, 29 Mar at 01:00 pm
Pinot's Palette - Logan Square
USD 56
Paint Night Done Right - Chicago - Paint and Sip in Chicago | Classpop!™
Sat, 14 Mar at 03:00 pm
Wolf Point Distilling
USD 55
Starry Night Ocean Tide - Paint and Sip in Chicago | Classpop!™
Sun, 22 Mar at 05:00 pm
Pinot's Palette - Logan Square
USD 56
Simply Starry Night "Your City" - Paint and Sip in Chicago | Classpop!™
Fri, 20 Mar at 08:00 pm
Pinot's Palette - Logan Square
USD 56
Ghostly Gardens - Paint and Sip in Chicago | Classpop!™
Fri, 03 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 at 03:30 pm
Pinot's Palette - Logan Square
USD 56
Monet's Chicago Twilight - Paint and Sip in Chicago | Classpop!™
Fri, 24 Apr at 08:00 pm
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
Van Gogh's Daisies and Poppies - Paint and Sip in Chicago | Classpop!™
Sun, 15 Mar at 01:00 pm
Pinot's Palette - Logan Square
USD 56
Van Gogh's Gladioli - Paint and Sip in Chicago | Classpop!™
Sat, 14 Mar at 03:30 pm
Pinot's Palette - Logan Square
USD 56
Manet's Lilacs in a Vase - Paint and Sip in Chicago | Classpop!™
Sat, 21 Mar at 03:00 pm
Pinot's Palette - Logan Square
USD 56
Shamrock Shenanigans - Paint and Sip in Chicago | Classpop!™
Sun, 15 Mar at 05:00 pm
Pinot's Palette - Logan Square
USD 56
Goldentide - Paint and Sip in Chicago | Classpop!™
Sat, 21 Mar at 07:30 pm
Pinot's Palette - Logan Square
USD 56
Goldentide - Paint and Sip in Chicago | Classpop!™
Wed, 25 Mar at 07:30 pm
Pinot's Palette - Logan Square
USD 32
Glowing Starry Night - Chicago - Paint and Sip in Chicago | Classpop!™
Thu, 26 Mar at 07:00 pm
Pinot's Palette - Logan Square
USD 56
Waterlilies, Monet Style - Paint and Sip in Chicago | Classpop!™
Sat, 28 Mar at 03:30 pm
Pinot's Palette - Logan Square
USD 56
Japanese Spring - Paint and Sip in Chicago | Classpop!™
Sun, 29 Mar at 05:00 pm
Pinot's Palette - Logan Square
USD 56
Eventide - Paint and Sip in Chicago | Classpop!™
Sat, 04 Apr at 07:30 pm
Pinot's Palette - Logan Square
USD 56
Van Gogh's Blue Vase - Paint and Sip in Chicago | Classpop!™
Sat, 04 Apr at 03:30 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
Under the Moonlight - Paint and Sip in Chicago | Classpop!™
Fri, 10 Apr at 08:00 pm
Pinot's Palette - Logan Square
USD 56
Navigating Home - Paint and Sip in Chicago | Classpop!™
Thu, 09 Apr at 07:00 pm
Pinot's Palette - Logan Square
USD 49
Van Gogh Les Iris - Paint and Sip in Chicago | Classpop!™
Sat, 11 Apr at 03:00 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
Cubist Portrait - Paint and Sip in Chicago | Classpop!™
Thu, 23 Apr at 07:30 pm
Pinot's Palette - Logan Square
USD 49
Spring Waterfall - Paint and Sip in Chicago | Classpop!™
Wed, 22 Apr at 07:00 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
Goldentide - Paint and Sip in Chicago | Classpop!™
Sun, 26 Apr at 05:00 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
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
My Happiest Hour - Paint and Sip in Chicago | Classpop!™
Sun, 26 Apr at 01:00 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
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
BYOB Sip & Paint Event - "Orchard Moonrise"
Fri, 20 Mar at 07:00 pm
Sip & Paint
USD 43
Japanese Rising Sun - Paint and Sip in Chicago | Classpop!™
Wed, 29 Apr at 07:30 pm
Pinot's Palette - Logan Square
USD 32
Ferxxo Sip and Paint: St. Patrick’s Celebration
Tue, 17 Mar at 07:00 pm
La Licor Panamericana
USD 36
Bridgeport Art Center Third Friday Open Studios March 2026
Fri, 20 Mar at 07:00 pm
Bridgeport Art Center Chicago
Free
R&B Night Paint & Sip
Sat, 14 Mar at 07:30 pm
Lux Accents Studios
USD 60 to 90
BYOB Paint and Sip Event - "Mystic Waterfalls"
Sat, 14 Mar at 07:00 pm
Sip & Paint
USD 43
R&B Night Paint & Sip
Sat, 28 Mar at 07:30 pm
Lux Accents Studios
USD 60 to 90
Cornelia Arts Building March Open Studios 2026
Fri, 20 Mar at 05:00 pm
1800 W Cornelia Ave, Chicago, IL, United States, Illinois 60657
Paint and Sip Drinkware Session - Paint and Sip in Chicago | Classpop!™
Tue, 17 Mar at 06:00 pm
KaLab
USD 40
Paint and Sip Drinkware Session - Paint and Sip in Chicago | Classpop!™
Tue, 24 Mar at 06:00 pm
KaLab
USD 40
BYOB Sip & Paint Class “Starry Night Skyline”
Sun, 22 Mar at 07:00 pm
Sip & Paint
USD 43
18+ Sober Opossum Paint & Sip
Sat, 28 Mar
The Insect Asylum
USD 32 to 96
St Patrick's Day BYOB Paint & Sip
Tue, 17 Mar at 04:00 pm
Art City
USD 50
Family Friendly Paint & Sip - Spring Break
Sat, 21 Mar at 01:00 pm
Art City
USD 0 to 44
Midwest Coast Brewing Co: Paint for Democracy!
Thu, 19 Mar at 06:00 pm
Sip & Paint
USD 50
Museica's BYOB Sip & Paint - Black Pumps Red Wine
Fri, 27 Mar at 07:00 pm
Museica's Art Studio
USD 45
Family Painting Event - "Hummingbirds" (Open to Adults and Kids 6+)
Sat, 21 Mar at 11:00 am
Sip & Paint
USD 38
Paint Your Date BYOB Paint & Sip
Sat, 17 Jan at 06:00 pm
Art City
USD 50
Playful Still Life Painting
Sat, 21 Mar at 01:00 pm
Lot'sa
USD 71
BYOB Paint & Sip: Tropical Moon Glow
Fri, 20 Mar at 07:30 pm
Lux Accents Studios
USD 61
Exhibit Opening Soiree - RIVER RAT - Artwork by Joel Berman.
Sat, 28 Mar at 05:00 pm
Swedish American Museum
Canvas & Cocktails: A Paint & Sip Experience
Sat, 28 Mar at 06:00 pm
210 N Racine Ave
USD 55
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
Figure Drawing Bootcamp
Wed, 04 Mar at 06:30 pm
Art City
USD 108
March 14 | Family Workshop: Screenpainting (2 Hours)
Sat, 14 Mar at 10:00 am
Spudnik Press
USD 150
Wicked-ly Fun Paint Party
Sat, 21 Mar at 11:00 am
Indgo MRKTO
USD 23 to 29
Get Lit: Art of the Cocktail
Tue, 12 May at 05:30 pm
American Writers Museum
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
Hemp, Health & Hibachi
Wed, 18 Mar at 07:00 pm
RISE Dispensary
USD 29 to 34
Intro to Figure Drawing Course- Part II
Sun, 15 Mar at 12:00 pm
LMN Wedge Studio & Gallery
USD 77 to 428
Your Photo, Your Painting - Paint and Sip in Chicago | Classpop!™
Wed, 25 Mar at 06:00 pm
KaLab
USD 46
DIY Mug or Wine Glass Painting - Art Class by Classpop!™
Fri, 27 Mar at 05:00 pm
KaLab
USD 40
Your Photo, Your Painting - Paint and Sip in Chicago | Classpop!™
Fri, 27 Mar at 05:00 pm
KaLab
USD 46
Your Photo, Your Painting - Paint and Sip in Chicago | Classpop!™
Fri, 20 Mar at 05:00 pm
KaLab
USD 46
Artisan Painted Bread Sip n' Paint + Baking Class
Sat, 04 Apr at 02:30 pm
Bettie's Chicago
USD 125
Paint and Sip at the Nest
Thu, 02 Apr at 06:00 pm
The Nest Bar & Eatery
USD 39
DIY Mug or Wine Glass Painting - Art Class by Classpop!™
Fri, 20 Mar at 05:00 pm
KaLab
USD 40
Paint & Sip
Fri, 24 Apr at 07:00 pm
RLM Studio
Free
Thursday nights - Special Sunday meetup, day after river dying green.
Sun, 15 Mar at 11:00 am
Vietnam Veterans Fountain
Community Canvas Autism Awareness Event
Sat, 25 Apr at 02:00 pm
Legler Regional Library, Chicago Public Library
Free
Opossum Paint Party for Kids
Sun, 22 Feb at 04:30 pm
The Insect Asylum
USD 32 to 73
Lincoln Park Zoo
Sat, 20 Jun at 12:00 pm
Lincoln Park Zoo
“You Are Loved” Sip and Paint
Sat, 28 Mar at 07:00 pm
Toast To Paint
USD 34 to 45
SKETCH / BOOK
Mon, 30 Mar at 06:00 pm
Quimby's Bookstore
USD 45
Café Urban Sketching with Amy Gowans
Sat, 28 Mar at 10:00 am
necessary & sufficient coffee - Printers Row, South Dearborn Street, Chicago, IL, USA
Free
Let's Sketch at Catalog Food Hall at Willis Tower
Sun, 22 Mar at 12:00 pm
Catalog at Willis Tower
Candle Painting
Tue, 31 Mar at 06:30 pm
Chi City Craft Club Studios
USD 61
Creativity Hoarders Anonymous (CHAnon)
Thu, 02 Apr at 05:30 pm
Harold Washington Library Center, Chicago Public Library, 8th Fl., Room 8S-14
Free
Collage Workshops with Paloma Trecka
Sun, 19 Apr at 01:00 pm
Oleander & Artesian
USD 55 to 87
St. Patrick’s Day Weekend Napkin Warz
Sun, 15 Mar at 09:00 pm
3001 W Peterson Ave
USD 29 to 45
Draw Now! Sunday Art Workshop
Sun, 01 Feb at 06:00 pm
Art City
USD 50
Sunday Funday Art Day
Sun, 07 Dec at 10:00 am
5420 W Belmont Ave
USD 8 to 43
Creativity Hoarders Anonymous (CHAnon)
Thu, 19 Mar at 05:30 pm
Harold Washington Library Center, Chicago Public Library, 8th Fl., Room 8S-14
Free
Pilsen Spring Sketchwalk
Sat, 16 May at 09:00 am
Pilsen, Chicago, Illinois
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Events in Chicago
Drawing-painting Events in Chicago