Drawing-painting Events in Chicago
Check out happening drawing-painting events all around Chicago, IL
Old Town Art Fair - Artist Nha Vuu and Chris Wheeler
Sat, 13 Jun at 10:00 am
Old Town Triangle Association
Chicago BYOB Exotic Paintings Sip and Paint with Male Models
Fri, 13 May at 07:30 pm
5425 W Lawrence Ave
USD 38
Chicago BYOB Sip and Paint with Male Models
Sun, 03 Mar at 08:00 pm
5425 W Lawrence Ave
USD 39
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
Chicago Exotic Paintings BYOB Wine and Paint Male Model
Fri, 10 Mar at 09:00 pm
5425 W Lawrence Ave
USD 39
Lincoln Roscoe Art + Craft Fair
Sat, 16 May at 10:00 am
N Lincoln Ave, Chicago, IL, United States
Sweet Sloth - Paint and Sip in Chicago | Classpop!™
Sun, 17 May at 01:00 pm
Pinot's Palette - Logan Square
USD 56
The Weeknd Sip and Paint in Chicago
Fri, 15 May at 07:00 pm
Mirella’s Tavern
USD 36
Colorful Chicago - Paint and Sip in Chicago | Classpop!™
Wed, 20 May at 07:00 pm
Pinot's Palette - Logan Square
USD 49
Art Battle Chicago - June 12, 2026
Fri, 12 Jun at 07:00 pm
SPIN Chicago
USD 20 to 29
Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™
Sat, 25 Jul
Studio W.I.P.
USD 62
Northern Night Lights - Paint and Sip in Chicago | Classpop!™
Fri, 29 May at 07:30 pm
Pinot's Palette - Logan Square
USD 56
Chicago Exotic Paintings BYOB Sip and Paint with Male Models
Fri, 26 Feb at 08:00 pm
5425 W Lawrence Ave
USD 43
Cubist Portrait - Paint and Sip in Chicago | Classpop!™
Thu, 23 Apr
Pinot's Palette - Logan Square
USD 49
Eventide - Paint and Sip in Chicago | Classpop!™
Sat, 23 May at 07:30 pm
Pinot's Palette - Logan Square
USD 56
Your City Night Glow - Paint and Sip in Chicago | Classpop!™
Sun, 17 May at 05:00 pm
Pinot's Palette - Logan Square
USD 56
Japanese Rising Sun - Paint and Sip in Chicago | Classpop!™
Fri, 22 May at 08:00 pm
Pinot's Palette - Logan Square
USD 32
R&B Night Paint & Sip
Sat, 23 May at 07:30 pm
Lux Accents Studios
USD 66 to 109
Galaxy Beach - Paint and Sip in Chicago | Classpop!™
Sat, 16 May at 07:30 pm
Pinot's Palette - Logan Square
USD 56
Pink Pantheress x Zara Larsson: Drag Paint and Sip
Thu, 28 May at 07:00 pm
Pinot's Palette
USD 39
Serene Sunrise - Paint and Sip in Chicago | Classpop!™
Sun, 24 May at 01:00 pm
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
Moonshine - Paint and Sip in Chicago | Classpop!™
Sat, 20 Jun at 07:30 pm
Pinot's Palette - Logan Square
USD 56
Candy Beach - Paint and Sip in Chicago | Classpop!™
Wed, 24 Jun 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
Dream Island - Paint and Sip in Chicago | Classpop!™
Wed, 06 May
Pinot's Palette - Logan Square
USD 32
R & Bling Thursdays
Thu, 16 Apr at 06:30 pm
KaLab Bronzeville
USD 66 to 215
Paint Your Date BYOB Paint & Sip
Sat, 17 Jan at 06:00 pm
Art City
USD 60
Figure Drawing - Props & Live Model with Lindsey Kircher
Sat, 16 May at 05:00 pm
Oliva Gallery
Free
Galaxy Waterfall Forest - Paint and Sip in Chicago | Classpop!™
Thu, 25 Jun at 07:30 pm
Pinot's Palette - Logan Square
USD 49
Dinosaurs in the Mist - Paint and Sip in Chicago | Classpop!™
Wed, 01 Jul at 07:00 pm
Pinot's Palette - Logan Square
USD 49
Tote Bag Paint Event
Sat, 16 May at 01:00 pm
Millennium Park
USD 29
Lakefront Art & Craft Vendor Market
Fri, 12 Jun at 08:00 am
Artifact Events
Free
The Brush Hour: A BYOV(ibes) Paint & Sip Experience
Sat, 23 May at 07:30 pm
2147 S Lumber St
Free
80s vs 90s Karaoke
Mon, 18 May at 09:00 pm
Replay Andersonville
Free
May Flowers Sip & Paint Night at Eris Brewery!
Wed, 20 May at 06:30 pm
ERIS Brewery and Cider House
USD 17 to 31
Moonlit Cherry Blossom River - Paint and Sip in Chicago | Classpop!™
Wed, 17 Jun at 07:00 pm
Pinot's Palette - Logan Square
USD 49
Cosplay Figure Drawing Class with Eli Estrella Pérez @Dark Tower Comics
Sat, 16 May at 05:00 pm
DARK TOWER COMICS - LOGAN SQUARE
USD 26
Sip & Paint | BYOB Cinco De Mayo Edition
Sat, 30 May at 02:00 pm
Nitro Nostalgia
USD 50
Doormat Paint, Sip & Karaoke Night
Fri, 29 May at 07:00 pm
4803 N Milwaukee Ave
USD 10 to 474
Suminagashi: Meditative Marbling on Silk & Paper at Wolf Point Distilling
Thu, 11 Jun at 05:30 pm
Wolf Point Distilling
USD 105
18+ Sober Opossum Paint & Sip
Sat, 28 Feb at 06:00 pm
The Insect Asylum
USD 32 to 96
Sunday Funday Art Day
Sun, 07 Dec at 10:00 am
5420 W Belmont Ave
USD 8 to 43
Artisan Painted Bread Sip n' Paint + Baking Class
Sat, 04 Apr
Bettie's Chicago
USD 125
Riso Quest
Sun, 31 May at 01:00 pm
Lot'sa
USD 55
Chicago Exotic Paintings BYOB Paint n Sip
Sat, 10 Aug at 04:00 pm
5425 W Lawrence Ave
USD 35
Copy of Intentional & Elevated: A Meditative Drawing Workshop
Sun, 14 Jun at 03:30 pm
Fulton Street Collective
USD 25
Abstract Florals: Loosening Up with the Burridge Method
Sat, 23 May at 02:00 pm
AponteArt Gallery
USD 45
Puff and Paint
Sun, 24 May at 06:00 pm
501 1/2 E 47th St
USD 23
Foraging in the Courtyard with The Wild Dryad
Sat, 15 Aug at 11:00 am
Jane Addams Hull-House Museum
Free
Head In The Clouds: Pick a Vinyl, Paint a Vinyl
Sun, 14 Jun at 03:00 pm
Bridgeport Records
USD 18
Story Makers: Write, Illustrate, and Bind your own Book
Fri, 10 Jul at 09:00 am
The WasteShed
USD 215
Paint the Chicago Skyline with Kenny
Sat, 16 May at 02:00 pm
Hey, I Thought Of You
USD 40
Lincoln Park Zoo
Sat, 20 Jun at 12:00 pm
Lincoln Park Zoo
Mahjong Tile Painting and Play!
Fri, 22 May at 07:00 pm
2220 W Lawrence Ave
USD 50
Pilsen Spring Sketchwalk
Sat, 16 May at 09:00 am
Pilsen, Chicago, Illinois
Free - Princess Etch Teaches How to Draw on an Etch a Sketch
Wed, 01 Jul at 03:00 pm
Hey, I Thought Of You
Free
Chicago Exotic Paintings BYOB Wine & Paint Male Models
Fri, 29 Jul at 07:00 pm
5425 W Lawrence Ave
USD 44
Opossum Paint Party for Kids ages 5-17
Sun, 22 Feb at 04:30 pm
The Insect Asylum
USD 32 to 73
Drop-In Figure Drawing
Sat, 17 Jan at 11:00 am
Art City
USD 30
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
Paint Your Pet BYOB Paint & Sip
Sun, 18 Jan at 02:00 pm
Art City
USD 59
Gouache Landscape Painting
Sat, 07 Feb at 12:00 pm
Lot'sa
USD 71
Art City BYOB Paint & Sip
Tue, 10 Feb at 01:00 pm
Art City
USD 59
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
TAKEOVER TUESDAYS SIP & PAINT PARTY
Tue, 17 Mar at 07:00 pm
8022 S Cottage Grove Ave
Free
DIY Faux Stained Glass
Fri, 01 Aug at 02:00 pm
5420 W Belmont Ave
USD 23 to 55
Linocut Block Printing Art Workshop
Mon, 25 Mar at 07:00 pm
Epic Art House
USD 7 to 109
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
Painting Pottery
Thu, 02 Oct at 12:00 pm
5127 N Clark St
USD 30
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Events in Chicago
Drawing-painting Events in Chicago