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 03:00 pm
Old Town Triangle Association
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
Art Battle Chicago - June 12, 2026
Fri, 12 Jun at 07:00 pm
SPIN Chicago
USD 20 to 29
Painting Poppies - Paint and Sip in Chicago | Classpop!™
Sun, 14 Jun at 01:00 pm
Pinot's Palette - Logan Square
USD 56
Sunrise Lake - Paint and Sip in Chicago | Classpop!™
Fri, 10 Jul at 08:00 pm
Pinot's Palette - Logan Square
USD 56
Monet Inspired Flower Beds - Paint and Sip in Chicago | Classpop!™
Sun, 21 Jun at 01:00 pm
Pinot's Palette - Logan Square
USD 56
Celestial City - Paint and Sip in Chicago | Classpop!™
Sun, 21 Jun at 05:00 pm
Pinot's Palette - Logan Square
USD 56
Galaxy Waterfall Forest - Paint and Sip in Chicago | Classpop!™
Thu, 25 Jun at 07:30 pm
Pinot's Palette - Logan Square
USD 49
Flamingo Beach - Paint and Sip in Chicago | Classpop!™
Thu, 25 Jun at 01:00 pm
Pinot's Palette - Logan Square
USD 49
Cosmic Reflection - Paint and Sip in Chicago | Classpop!™
Fri, 26 Jun at 08:00 pm
Pinot's Palette - Logan Square
USD 56
Galaxy Beach - Paint and Sip in Chicago | Classpop!™
Fri, 03 Jul at 08:00 pm
Pinot's Palette - Logan Square
USD 56
Monet's Chicago Twilight - Paint and Sip in Chicago | Classpop!™
Sat, 18 Jul at 07:30 pm
Pinot's Palette - Logan Square
USD 56
Moon Over Catalina - Paint and Sip in Chicago | Classpop!™
Wed, 08 Jul at 07:00 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
Monet’s Water Lilies II - Paint and Sip in Chicago | Classpop!™
Sat, 11 Jul at 03:30 pm
Pinot's Palette - Logan Square
USD 56
Japanese Crimson Moon - Paint and Sip in Chicago | Classpop!™
Sat, 11 Jul at 07:30 pm
Pinot's Palette - Logan Square
USD 56
Glow River - Paint and Sip in Chicago | Classpop!™
Fri, 17 Jul at 08:00 pm
Pinot's Palette - Logan Square
USD 56
Glowing Starry Night - Chicago - Paint and Sip in Chicago | Classpop!™
Thu, 23 Jul at 07:00 pm
Pinot's Palette - Logan Square
USD 49
Seas the Day - Paint and Sip in Chicago | Classpop!™
Sun, 26 Jul at 05:00 pm
Pinot's Palette - Logan Square
USD 56
Van Gogh's Blue Vase - Paint and Sip in Chicago | Classpop!™
Sat, 25 Jul at 03:30 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
Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™
Sat, 25 Jul
Studio W.I.P.
USD 62
Japanese Rising Sun - Paint and Sip in Chicago | Classpop!™
Wed, 29 Apr
Pinot's Palette - Logan Square
USD 32
Paint Bouquets & Sip - Awakenings Fundraiser
Wed, 17 Jun at 06:00 pm
Awakenings
USD 55 to 75
Starry Southwest Galaxy - Paint and Sip in Chicago | Classpop!™
Sun, 14 Jun at 05:00 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
Moonlit Cherry Blossom River - Paint and Sip in Chicago | Classpop!™
Wed, 17 Jun at 07:00 pm
Pinot's Palette - Logan Square
USD 49
Mystical Mountain View - Paint and Sip in Chicago | Classpop!™
Fri, 26 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
Summer’s Point - Paint and Sip in Chicago | Classpop!™
Sun, 05 Jul at 01:00 pm
Pinot's Palette - Logan Square
USD 56
Galaxy Lake - Paint and Sip in Chicago | Classpop!™
Wed, 15 Jul at 07:00 pm
Pinot's Palette - Logan Square
USD 49
Dream Island - Paint and Sip in Chicago | Classpop!™
Wed, 06 May
Pinot's Palette - Logan Square
USD 32
Waterlilies, Monet Style - Paint and Sip in Chicago | Classpop!™
Sun, 26 Jul at 01:00 pm
Pinot's Palette - Logan Square
USD 56
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 59
R&B Night Paint & Sip: Sunset Over the City
Sat, 13 Jun at 07:30 pm
Lux Accents Studios
USD 66 to 109
JESSE MICHAELS + MATT SKIBA ART EXHIBTION IN CHICAGO
Thu, 30 Jul at 06:00 pm
Elephant Room Gallery
Bridgeport Art Center Third Friday Open Studios June 2026
Fri, 19 Jun at 07:00 pm
Bridgeport Art Center Chicago
Free
Chicago Exotic Paintings BYOB Wine and Paint Male Model
Fri, 10 Mar at 09:00 pm
5425 W Lawrence Ave
USD 44
Leo Main Character Paint & Sip
Sat, 25 Jul at 07:00 pm
4803 N Milwaukee Ave
USD 10 to 474
Lakefront Art & Craft Vendor Market
Fri, 12 Jun at 08:00 am
Artifact Events
Free
SUMMERTIME Remedy Bar Paint and Sip!!
Tue, 30 Jun at 06:30 pm
Remedy
USD 71
The Time Machine: The First Portal | 90s-2000s Paint & Sip Experience
Sat, 06 Jun at 06:30 pm
Tribe, A Healing Arts Community
USD 0 to 55
Doormat Paint, Sip & Karaoke Night
Sat, 11 Jul at 07:00 pm
4803 N Milwaukee Ave
USD 10 to 474
Paint & Sip at Su Taqueria Thaly's THURSDAY JUNE 11 6:30pm to 8:30pm
Thu, 11 Jun at 06:30 pm
Su Taqueria Thaly's
USD 49
Suminagashi: Meditative Marbling on Silk & Paper at Wolf Point Distilling
Thu, 11 Jun at 05:30 pm
Wolf Point Distilling
USD 105
Artecito Axolotl @ Blue Door Neighborhood Center
Sat, 20 Jun at 10:00 am
2551 W Cermak Ave Chicago, IL 60608
Sketch Workshop at BrentArt SUNDAY JUNE 14: 2:00pm to 4:00pm
Sun, 14 Jun at 02:00 pm
BrentArt
USD 49
Cat's Sketch Pad
Mon, 08 Jun at 05:00 pm
4018 N Cicero Ave
Free
Copy of Intentional & Elevated: A Meditative Drawing Workshop
Sun, 14 Jun at 03:30 pm
Fulton Street Collective
USD 25
Learn to Draw a Landscape with Geanina
Sat, 20 Jun at 02:00 pm
Hey, I Thought Of You
USD 40
Marsupial Masterpiece: Opossum Paint and Sip! +21 BYOB
Sun, 07 Sep at 06:00 pm
The Insect Asylum
USD 96
Chicago Exotic Paintings BYOB Paint n Sip
Sat, 10 Aug at 04:00 pm
5425 W Lawrence Ave
USD 35
Head In The Clouds: Pick a Vinyl, Paint a Vinyl
Sun, 14 Jun at 03:00 pm
Bridgeport Records
USD 18
Chicago Exotic Paintings BYOB Wine & Paint Male Models
Fri, 29 Jul at 07:00 pm
5425 W Lawrence Ave
USD 44
Foraging in the Courtyard with The Wild Dryad
Sat, 15 Aug at 11:00 am
Jane Addams Hull-House Museum
Free
Art City Open Studios
Fri, 27 Mar at 06:00 pm
Art City
Free
Lincoln Park Zoo
Sat, 20 Jun at 12:00 pm
Lincoln Park Zoo
Summer E-tegami Workshop: June Vegetables at Gaijin
Sun, 28 Jun at 03:00 pm
Gaijin
USD 34
8-Week Drawing Course for Beginners
Sat, 23 May at 11:45 am
Studio LMN / Wedge Gallery
USD 70 to 450
VIRGO VISION BOARD PAINT & SIP NIGHT
Sat, 12 Sep at 07:00 pm
4803 N Milwaukee Ave
USD 28 to 297
Painting Dreamscapes - Expressive Painting Workshop
Wed, 24 Jun at 06:00 pm
Awakenings
Free
Free Street's Open Hours: Arts & Healing
Tue, 10 Feb at 06:00 pm
4625 S Ashland Ave
Free
Open Gallery Hours: Oliva Gallery
Sat, 13 Jun at 12:00 pm
Oliva Gallery
Free
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
One-time Pottery Class & Painting - Lakeview
Fri, 01 Aug at 10:00 am
3262 N Clark St
USD 141
Drop-In Figure Drawing
Sat, 17 Jan at 11:00 am
Art City
USD 25
Wednesday Figure Drawing Session with Live Model
Wed, 28 May at 06:00 pm
1579 N Milwaukee Ave suite 206
USD 23 to 135
Paint Your Pet BYOB Paint & Sip
Sun, 18 Jan at 02:00 pm
Art City
USD 59
Art City BYOB Paint & Sip
Tue, 10 Feb at 01:00 pm
Art City
USD 59
Cacti Watercolor Workshop
Mon, 17 Nov at 12:00 pm
5420 W Belmont Ave
USD 26
DIY Stamp Carving
Tue, 08 Jul at 05:00 pm
5420 W Belmont Ave
USD 23
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
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