Painting Events in Chicago
Check out happening 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
Millennium Art Festival
Sat, 27 Jun at 10:00 am
180 N Stetson Ave
Free
Gold Coast Art Fair (68th annual)
Sat, 20 Jun at 10:00 am
Grant Park
Millennium Art Festival
Sat, 27 Jun at 10:00 am
Michigan Ave & E Lake St, Chicago
Painting Poppies - Paint and Sip in Chicago | Classpop!™
Sun, 14 Jun at 01:00 pm
Pinot's Palette - Logan Square
USD 56
Smokey Mountain Morning - Paint and Sip in Chicago | Classpop!™
Fri, 12 Jun at 08:00 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
Flamingo Beach - Paint and Sip in Chicago | Classpop!™
Thu, 25 Jun at 01:00 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
Wild Flower Forest - Paint and Sip in Chicago | Classpop!™
Sat, 27 Jun at 03:00 pm
Pinot's Palette - Logan Square
USD 56
Blossoming Charm - Paint and Sip in Chicago | Classpop!™
Sun, 28 Jun
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
Galaxy Beach - Paint and Sip in Chicago | Classpop!™
Fri, 03 Jul at 08:00 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
Golden Peace - Paint and Sip in Chicago | Classpop!™
Thu, 09 Jul at 07:30 pm
Pinot's Palette - Logan Square
USD 49
Monet's Chicago Twilight - Paint and Sip in Chicago | Classpop!™
Sat, 18 Jul at 07:30 pm
Pinot's Palette - Logan Square
USD 56
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
Groovy Lava Lamp - Paint and Sip in Chicago | Classpop!™
Thu, 02 Jul at 07:00 pm
Pinot's Palette - Logan Square
USD 49
Glow River - Paint and Sip in Chicago | Classpop!™
Fri, 17 Jul at 08:00 pm
Pinot's Palette - Logan Square
USD 56
Navy Pier Rooftop Paint and Sip!
Thu, 11 Jun at 06:00 pm
Offshore-Navy Pier
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
Glowing Starry Night - Chicago - Paint and Sip in Chicago | Classpop!™
Thu, 23 Jul at 07:00 pm
Pinot's Palette - Logan Square
USD 49
Stardust River - Paint and Sip in Chicago | Classpop!™
Thu, 23 Jul at 07:30 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
Chicago Exotic Paintings BYOB Sip and Paint with Male Models
Fri, 26 Feb at 08:00 pm
5425 W Lawrence Ave
USD 43
Simply A Starry Night - Paint and Sip in Chicago | Classpop!™
Wed, 22 Apr
Pinot's Palette - Logan Square
USD 32
Vibrance
Sat, 06 Jun
301 W Ohio St
Free
Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™
Sat, 25 Jul
Studio W.I.P.
USD 62
Bad Bunny Sip and Paint
Sat, 13 Jun at 07:00 pm
Toast To Paint
USD 34 to 45
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
Juneteenth Weekend Sip and Paint
Sat, 20 Jun at 07:00 pm
Toast To Paint
USD 34 to 45
PRIDE Drag Paint & Sip: Studio 54
Thu, 18 Jun at 07:00 pm
Pinot's Palette
USD 7 to 47
Father's Day 21+ BYOB Opossum Paint & Sip
Sun, 21 Jun at 06:00 pm
The Insect Asylum
USD 96
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
Celestial City - Paint and Sip in Chicago | Classpop!™
Sun, 21 Jun at 05:00 pm
Pinot's Palette - Logan Square
USD 56
Sweet Sloth - Paint and Sip in Chicago | Classpop!™
Tue, 23 Jun at 02:00 pm
Pinot's Palette - Logan Square
USD 44
Mystical Mountain View - Paint and Sip in Chicago | Classpop!™
Fri, 26 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
Soirée
Sun, 21 Jun at 03:00 pm
Barcocina West Town (Chicago)
Candy Beach - Paint and Sip in Chicago | Classpop!™
Wed, 24 Jun at 07:00 pm
Pinot's Palette - Logan Square
USD 49
Misty Mountain Galaxy - Paint and Sip in Chicago | Classpop!™
Thu, 02 Jul at 07:30 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
Bridgeport Art Center Third Friday Open Studios June 2026
Fri, 19 Jun at 07:00 pm
Bridgeport Art Center Chicago
Free
Galaxy Lake - Paint and Sip in Chicago | Classpop!™
Wed, 15 Jul at 07:00 pm
Pinot's Palette - Logan Square
USD 49
Bloom & Pour - Fragrance/Candle Making +Bloom Bar
Fri, 08 May at 01:00 pm
3414 W Foster Ave
USD 71 to 141
Waterlilies, Monet Style - Paint and Sip in Chicago | Classpop!™
Sun, 26 Jul at 01:00 pm
Pinot's Palette - Logan Square
USD 56
18+ Sober Opossum Paint & Sip
Sat, 28 Feb at 06:00 pm
The Insect Asylum
USD 32 to 96
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
CHRIS BROWN VS USHER SIP & PAINT
Sun, 02 Aug at 03:00 pm
Event space
USD 67 to 120
Chicago Exotic Paintings BYOB Wine and Paint Male Model
Fri, 10 Mar at 09:00 pm
5425 W Lawrence Ave
USD 44
Sunday In The Park With George
Thu, 13 Aug at 07:00 pm
Chopin Theatre
USD 25 to 109
Kintsugi Workshop: Repair and Reconnect
Sat, 06 Jun
International Museum of Surgical Science
USD 82
Japanese Bookbinding: Goshuinchō & Yotsume Toji
Thu, 16 Jul at 05:30 pm
Japanese Culture Center
USD 52
Bad & Boujee Exotic Paint & Sip – BYOB Edition! CHICAGO
Fri, 14 Mar at 09:00 pm
5425 W Lawrence Ave
USD 45
BYOB Sip & Paint Event - "Blooming Bridge"
Wed, 10 Jun at 07:00 pm
Sip & Paint
USD 43
BYOB Sip & Paint Event - "Spring in Paris"
Thu, 11 Jun at 07:00 pm
Sip & Paint
USD 43
Paint & Sip at El Azteca - Armitage Thursday June 18
Thu, 18 Jun at 06:30 pm
El Azteca
USD 49
Juneteenth Sip and Paint
Fri, 19 Jun at 07:00 pm
Toast To Paint
USD 45
June Book Club & Paint by Numbers Picnic: My Friends
Sat, 27 Jun at 03:00 pm
Belmont Harbor
USD 20 to 27
SUMMERTIME Remedy Bar Paint and Sip!!
Tue, 30 Jun at 06:30 pm
Remedy
USD 71
Dragonflies & Florals A Sip and Paint At Eris Brewery and Cider House
Wed, 24 Jun at 06:30 pm
ERIS Brewery and Cider House
USD 17 to 31
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
Petalo: Myth of Us Opening Night
Fri, 26 Jun at 06:00 pm
2800 N Milwaukee Ave
Free
Art City June Receptions - Helena Celewics, Carol Schrader, and Group Show
Fri, 12 Jun at 05:00 pm
Art City
Free
Artisan Painted Bread Sip n' Paint + Baking Class
Sat, 11 Jul at 03:00 pm
Bettie's Chicago
USD 125
BYOB Paint & Sip: Dream Catcher
Sun, 14 Jun at 01:30 pm
Lux Accents Studios
USD 61
Puff and Paint
Sun, 28 Jun at 06:00 pm
501 1/2 E 47th St
USD 23
Queer Couples Stained Glass Picture Frames - 2 Sessions
Sat, 20 Jun at 03:00 pm
The WasteShed
USD 322
Opossum Paint Party for Kids ages 5-17
Sun, 22 Feb at 04:30 pm
The Insect Asylum
USD 32 to 73
Live Handpainting Demo
Tue, 09 Jun at 01:00 pm
ASID Illinois Chapter
Free
Draw Now! Sunday Art Workshop
Sun, 01 Feb at 06:00 pm
Art City
USD 61
Suminagashi: Meditative Marbling on Silk & Paper at Wolf Point Distilling
Thu, 11 Jun at 05:30 pm
Wolf Point Distilling
USD 105
Coffee Painting (All Ages)
Sat, 06 Jun at 10:00 am
5420 W Belmont Ave
USD 26
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
Kintsugi for Beginners
Fri, 20 Mar
Japanese Culture Center
USD 130
Advanced Kintsugi: Traditional Method (4-Week Course)
Thu, 18 Jun at 05:30 pm
Japanese Culture Center
USD 215
Wings & Wine Glass Painting
Wed, 08 Apr at 04:00 pm
KaLab Bronzeville
USD 29
Interwoven
Sat, 27 Jun at 03:00 pm
7644 S Greenwood Ave
Free
Art City Open Studios
Fri, 27 Mar at 06:00 pm
Art City
Free
Tote Bag Workshop @ Ridman's Coffee
Sat, 11 Jul at 03:30 pm
Ridman's Coffee
USD 34
Cake Decorating Workshop: Faux Frosting
Thu, 06 Aug at 04:30 pm
Oliva Gallery
USD 11
Summer E-tegami Workshop: July Fruits & flowers
Sat, 25 Jul at 03:30 pm
Japanese Culture Center
USD 34
Introduction to Encaustic Materials and Demonstration with Jane Michalski
Sun, 09 Aug at 10:00 am
Oliva Gallery
USD 14
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
Pilsen Neighborhood Art & Walking Tour
Sat, 27 Jun at 12:00 pm
Pilsen Yards
CONVERGENCE: Katherine Ratay and Alfred Wills
Thu, 11 Jun at 05:00 pm
Artruss Gallery
Free
VIRGO VISION BOARD PAINT & SIP NIGHT
Sat, 12 Sep at 07:00 pm
4803 N Milwaukee Ave
USD 28 to 297
Chicago Bad & Boujee Exotic Paint & Sip – BYOB Edition!
Fri, 11 Jul at 08:00 pm
5425 W Lawrence Ave
USD 45
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Events in Chicago
Painting Events in Chicago