Drawing-painting Events in Chicago
Check out happening drawing-painting events all around Chicago, IL
Chicago BYOB Sip and Paint with Male Models
Sun, 03 Mar at 08:00 pm
5425 W Lawrence Ave
USD 39
Chicago BYOB Exotic Paintings Sip and Paint with Male Models
Fri, 13 May at 07:30 pm
5425 W Lawrence Ave
USD 38
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
Moonlit Swan Lake - Paint and Sip in Chicago | Classpop!™
Sat, 09 May at 07:30 pm
Pinot's Palette - Logan Square
USD 56
Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™
Sat, 28 Feb
Studio W.I.P.
USD 62
Chicago Exotic Paintings BYOB Sip and Paint with Male Models
Fri, 26 Feb at 08:00 pm
5425 W Lawrence Ave
USD 43
My Happiest Hour - Paint and Sip in Chicago | Classpop!™
Sun, 26 Apr at 01:00 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
Spring Tulips Tea Tray - Paint and Sip in Chicago | Classpop!™
Sat, 02 May at 04:00 pm
Pinot's Palette - Logan Square
USD 68
Mini - Love Mom Flowers - Paint and Sip in Chicago | Classpop!™
Sun, 10 May at 10:30 am
Pinot's Palette - Logan Square
USD 44
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
Monet’s Water Lilies II - Paint and Sip in Chicago | Classpop!™
Sat, 18 Apr
Pinot's Palette - Logan Square
USD 56
Eventide - Paint and Sip in Chicago | Classpop!™
Sat, 23 May
Pinot's Palette - Logan Square
USD 56
Colorful Wave - Paint and Sip in Chicago | Classpop!™
Fri, 05 Jun at 07:30 pm
Pinot's Palette - Logan Square
USD 56
Moonlit Cherry Blossom River - Paint and Sip in Chicago | Classpop!™
Wed, 17 Jun 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
Moon Glow Forest - Paint and Sip in Chicago | Classpop!™
Sun, 03 May at 05:00 pm
Pinot's Palette - Logan Square
USD 56
Green Forest Falls - Paint and Sip in Chicago | Classpop!™
Fri, 01 May at 08:00 pm
Pinot's Palette - Logan Square
USD 56
Art Battle Chicago - June 12, 2026
Fri, 12 Jun at 07:00 pm
SPIN Chicago
USD 20 to 29
Firefly Falls - Paint and Sip in Chicago | Classpop!™
Wed, 29 Apr at 07:00 pm
Pinot's Palette - Logan Square
USD 49
Monet Inspired Flower Beds - Paint and Sip in Chicago | Classpop!™
Sun, 21 Jun at 01:00 pm
Pinot's Palette - Logan Square
USD 56
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
Chicago Exotic Paintings BYOB Wine and Paint Male Model
Fri, 10 Mar at 09:00 pm
5425 W Lawrence Ave
USD 39
Galaxy Waterfall Forest - Paint and Sip in Chicago | Classpop!™
Thu, 25 Jun at 07:30 pm
Pinot's Palette - Logan Square
USD 49
Moonshine - Paint and Sip in Chicago | Classpop!™
Sat, 20 Jun at 07:30 pm
Pinot's Palette - Logan Square
USD 56
Fairy Cottage - Paint and Sip in Chicago | Classpop!™
Sat, 09 May at 11:30 am
Pinot's Palette - Logan Square
USD 50
Dinosaurs in the Mist - Paint and Sip in Chicago | Classpop!™
Wed, 01 Jul at 07:00 pm
Pinot's Palette - Logan Square
USD 49
Midnight Glow - Paint and Sip in Chicago | Classpop!™
Thu, 14 May at 07:30 pm
Pinot's Palette - Logan Square
USD 49
Van Gogh's Blue Vase - Paint and Sip in Chicago | Classpop!™
Sat, 04 Apr
Pinot's Palette - Logan Square
USD 56
Monet's Chicago Twilight - Paint and Sip in Chicago | Classpop!™
Fri, 24 Apr
Pinot's Palette - Logan Square
USD 56
Goldentide - Paint and Sip in Chicago | Classpop!™
Sun, 26 Apr
Pinot's Palette - Logan Square
USD 56
Dream Island - Paint and Sip in Chicago | Classpop!™
Wed, 06 May
Pinot's Palette - Logan Square
USD 32
Your City Night Glow - Paint and Sip in Chicago | Classpop!™
Thu, 30 Apr
Pinot's Palette - Logan Square
USD 56
Van Gogh's Gladioli - Paint and Sip in Chicago | Classpop!™
Sun, 31 May at 01:00 pm
Pinot's Palette - Logan Square
USD 56
Lilacs in a Glass - Paint and Sip in Chicago | Classpop!™
Sat, 30 May at 03:30 pm
Pinot's Palette - Logan Square
USD 56
BYOB Sip & Paint Event - "Tropical Paradise"
Sat, 25 Apr at 07:00 pm
Chicago Sip & Paint
USD 43
Mirada Sip and Paint in Chicago
Fri, 01 May at 07:00 pm
Mirella’s Tavern
USD 36
Sip + Paint
Sun, 03 May at 06:00 pm
Khepri Cafe
USD 10 to 61
Cubist Portrait - Paint and Sip in Chicago | Classpop!™
Thu, 23 Apr
Pinot's Palette - Logan Square
USD 49
Moon Over the Pines - Paint and Sip in Chicago | Classpop!™
Sat, 02 May
Pinot's Palette - Logan Square
USD 56
Waterlilies, Monet Style - Paint and Sip in Chicago | Classpop!™
Sun, 12 Apr
Pinot's Palette - Logan Square
USD 56
Mother's Day & Mimosas — A Special Paint & Sip Experience
Fri, 08 May at 01:00 pm
Art City
USD 90
Japanese Rising Sun - Paint and Sip in Chicago | Classpop!™
Wed, 29 Apr
Pinot's Palette - Logan Square
USD 32
Mother's Day Brunch & Blooms Paint n' Sip
Sat, 09 May at 11:00 am
Studio15 / TVP Tech Solutions LLC
USD 61
Emotional Support Animals by Nicole J. Georges with Jessica Hopper
Thu, 30 Apr at 07:00 pm
Women & Children First
Free
18+ Sober Opossum Paint & Sip
Sat, 28 Feb at 06:00 pm
The Insect Asylum
USD 32 to 96
Paint Your Date BYOB Paint & Sip
Sat, 17 Jan at 06:00 pm
Art City
USD 55
The Brush Hour: A BYOV(ibes) Paint & Sip Experience
Sat, 25 Apr at 07:30 pm
2147 W Lumber St
Free
Drink & Draw April
Mon, 27 Apr at 07:00 pm
Beermiscuous
Free
Chicago Exotic Paintings BYOB Paint n Sip
Sat, 10 Aug at 04:00 pm
5425 W Lawrence Ave
USD 35
Get Lit: Art of the Cocktail
Tue, 12 May at 05:30 pm
American Writers Museum
Tote Bag Paint Event
Sat, 16 May at 01:00 pm
Millennium Park
USD 29
Build Your Dream Garden with Young Cultural Stewards
Sat, 09 May at 11:00 am
Jane Addams Hull-House Museum
Free
May Flowers Sip & Paint Night at Eris Brewery!
Wed, 20 May at 06:30 pm
ERIS Brewery and Cider House
USD 31
Mother's Day: Mom + Me Paint Party
Sat, 09 May at 02:00 pm
4803 N Milwaukee Ave
USD 23 to 93
Paint & Sip
Fri, 24 Apr at 07:00 pm
RLM Studio
Free
Sip & Paint | BYOB Cinco De Mayo Edition
Sat, 30 May at 02:00 pm
Nitro Nostalgia
USD 50
Playful Still Life Painting
Sat, 09 May at 01:00 pm
Lot'sa
USD 71
Community Canvas Autism Awareness Event
Sat, 25 Apr at 02:00 pm
Legler Regional Library, Chicago Public Library
Free
Pilsen Spring Sketchwalk
Sat, 16 May at 09:00 am
Pilsen, Chicago, Illinois
Lincoln Park Zoo
Sat, 20 Jun at 12:00 pm
Lincoln Park Zoo
Open Paint Night Fridays
Fri, 03 Apr at 06:00 pm
Studio15 / TVP Tech Solutions LLC
USD 34
Your Photo, Your Painting - Paint and Sip in Chicago | Classpop!™
Fri, 20 Mar
KaLab
USD 46
Opossum Paint Party for Kids ages 5-17
Sun, 22 Feb at 04:30 pm
The Insect Asylum
USD 32 to 73
Intro to Figure Drawing Course
Sun, 26 Apr at 12:00 pm
LMN Wedge Studio & Gallery
USD 77 to 258
Artisan Painted Bread Sip n' Paint + Baking Class
Sat, 04 Apr
Bettie's Chicago
USD 125
QCDC Project Windows Abstract Art Creative Experience
Fri, 01 May at 03:00 pm
Ka'Lab: The Creative Space
Free
Chicago Paint ,Play And Picnic Experience
Fri, 08 May at 08:00 am
337 E Randolph St
Free
Collage Workshops with Paloma Trecka
Sun, 19 Apr at 01:00 pm
Oleander & Artesian
USD 55 to 87
Paint the Chicago Skyline with Kenny
Sat, 16 May at 02:00 pm
Hey, I Thought Of You
USD 40
Draw Now! Sunday Art Workshop
Sun, 01 Feb at 06:00 pm
Art City
USD 55
Figure Drawing Bootcamp
Wed, 04 Mar at 06:30 pm
Art City
USD 119
Story Makers: Write, Illustrate, and Bind your own Book
Fri, 10 Jul at 09:00 am
The WasteShed
USD 215
Chicago Exotic Paintings BYOB Wine & Paint Male Models
Fri, 29 Jul at 07:00 pm
5425 W Lawrence Ave
USD 44
Pearls of Wisdom Paint & Praise
Sat, 02 May at 02:00 pm
God's House of All Nations
USD 39
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
Art City Open Studios
Fri, 27 Mar at 06:00 pm
Art City
USD 28
SKETCH / BOOK
Mon, 30 Mar at 06:00 pm
Quimby's Bookstore
USD 45
Gouache Landscape Painting
Sat, 07 Feb at 12:00 pm
Lot'sa
USD 71
FREE PAINTING / SCULPTURE WORKSHOP!!!!
Sat, 09 May at 01:00 pm
Forum 301
Free
FREE - Mother’s Day Coloring Afternoon
Sun, 10 May at 03:00 pm
Hey, I Thought Of You
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
Drawing Club: Ongoing Drawing Course for Beginners+
Fri, 11 Oct at 09:30 am
Studio LMN / Wedge Gallery
USD 77 to 482
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 55
Cacti Watercolor Workshop
Mon, 17 Nov at 12:00 pm
5420 W Belmont Ave
USD 26
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Events in Chicago
Drawing-painting Events in Chicago