Chicago
Chicago Paint & Sip: Cocktails, Creativity, and Canvases!
120
Overview
Experience the fun of Paint Night and Cocktails at Trendy Venues Across Chicago. This isn't just another night out; it's a chance to unleash inner creativity with a hands-on paint and sip class in some of Chicago's coolest local spots. Participants can swap a regular evening for a relaxed painting session, complete with drinks, brushes, and plenty of laughter.
A local instructor will guide each step, so no prior experience is needed. It's all about having a good time while creating something unique, even if drawing isn't a strong suit. All essential materials are provided, including the canvas, brushes, paint, and an apron to keep clothes clean. The classes are held in trendy venues like breweries and bars, adding to the vibrant and social atmosphere.
Whether someone is looking for a unique date night, a fun team outing, or a solo adventure in self-care, this paint and sip class offers good vibes, great drinks, and a piece of art to take home. This experience creates a memorable night out in Chicago. 
Highlights
Creative Night Out: Enjoy a unique blend of art, drinks, and socializing in Chicago's trendy venues.
All Art Supplies Included: Canvas, brushes, paints, and apron are provided, so participants can focus on fun.
Beginner-Friendly: A talented instructor guides the class, making it easy for anyone to create a masterpiece.
Perfect for Any Occasion: Ideal for dates, girls' nights, team-building, or a creative solo escape.
Sentiment Analysis
Customers highlight the fun and relaxed atmosphere of the class.
-
Many appreciate the helpful and knowledgeable instructors.
-
Participants enjoy the opportunity to be creative and create their own artwork.
-
Several reviewers mention it's a great activity for groups, families, and individuals.
Some reviewers mention that the fumes from the paint can be strong, recommending face masks.
-
A few customers wished the class was longer.
The Journey
Trendy Chicago Venue
The experience takes place in a local Chicago bar or brewery, providing a relaxed and social atmosphere.
Painting Session
A local artist provides step-by-step instructions for creating a unique painting.
Know Before You Go
This paint and sip experience includes a cozy, creative class at a local Chicago bar, all necessary painting materials, a 2-hour class led by a talented instructor, and a canvas to take home. Drinks are not included and are available for purchase at the venue, with prices ranging from $3 to $20.
Hot Tip
Consider wearing clothes that can get paint on them, just in case, even though aprons are provided. Arrive a little early to grab a drink and get comfortable before the painting begins.
Review Summary
Reviews for paint night experiences in Chicago consistently praise the fun and casual atmosphere, friendly and encouraging instructors, and the creative outlet provided, even for those without artistic experience. Positive points include sociable environments often set in trendy bars or breweries, making it ideal for date nights or group outings. On the negative side, some customers note variability in venue quality, occasional difficulty with parking, and the need to confirm the exact location due to multiple hosting spots. Overall, travelers recommend the experience for a relaxed, entertaining evening with the added bonus of taking home a personalized artwork.
This page is complied by Dyvarcity Team
More like this
Chicago
$45
Chicago Spray Paint & Sip: Unleash Your Inner Artist!
4.8
(397 reviews)
Duration: 90
minutes
BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago is a unique and engaging experience that lets anyone tap into their creative side. This isn't just another paint night; it's an opportunity to explore the vibrant world of street art in an intimate gallery setting.
Participants will learn about different street art styles and techniques from guest artists before getting hands-on with aerosol spray and stencils. Studio W.I.P. provides all the materials needed for the workshop, and the Studio W.I.P. staff guide participants through each step, making it accessible for all skill levels. Best of all, you get to take your own artwork home on a mini-canvas from the communal wall!
This workshop offers a chance to explore the techniques of aerosol application, stencil design, and graffiti styles. It's a fun, relaxed environment to learn new skills and create a personalized piece of art.
Chicago
$60
Chicago T-Shirt Screen Printing Workshop: DIY Fashion!
5.0
(2 reviews)
Duration: 90
minutes
BYOT-shirt Screen Printing Workshop, located in Chicago, offers a fun and creative way to upcycle clothing and create unique wearable art. This workshop is perfect for beginners with no prior art experience, offering a hands-on introduction to the basics of screen printing. Participants will transform a t-shirt or sweatshirt they already own into a personalized masterpiece, making it a sustainable and memorable experience.
At Remade in Chicago, guests can choose from over 20 pre-made screen designs featuring bold and playful images. Expert instructors guide participants through the ink-pulling process, ensuring a successful and satisfying image transfer. While the workshop focuses on the printing process, curious guests can learn about designing and prepping screens.
This small-group workshop provides a creative and engaging afternoon for anyone looking to explore a new hobby or simply enjoy a hands-on artistic experience. It's an ideal way to express individuality and create a one-of-a-kind fashion statement.
Chicago
$85
Magnificent Mile Perfume Creation: Blend Your Signature Scent!
4.9
(41 reviews)
Duration: 75
minutes
Chicago Perfume Making Classes on Magnificent Mile invites you to design your personal fragrance. This hands-on workshop offers expert guidance, a vast selection of notes, and all tools. Craft a 1oz bottle of perfume, personalized to reflect your unique style. Perfect for individuals or small groups seeking a sensory and creative adventure.
Chicago
$75
Unleash Your Inner Artist: Chicago Candle Making on the Magnificent Mile
4.5
(20 reviews)
Duration: 75
minutes
Chicago Candle Making Class: Craft your own 100% soy wax candles on Magnificent Mile. Perfect for dates, girls' night, or solo fun. Learn candle-making techniques and customize fragrances. All supplies provided to create a unique 8 oz candle in a 60-75 minute session. A memorable and personalized experience awaits!
Chicago
$35
Chicago's Dazzling Architecture: Interiors Walking Tour
5.0
(1475 reviews)
Duration: 120
minutes
Original Chicago Architecture Interiors Tour: Dazzling Interiors takes guests on a journey through some of the city's most breathtaking interior spaces. Many people pass by these hidden gems every day without realizing what's inside. This walking tour, led by an experienced local guide, reveals the stunning beauty within.
Guests will explore architectural wonders, from turn-of-the-century stained glass mosaics to soaring Art Deco designs from the Roaring 20s. Key stops include the iconic Art Deco Building, Surprise Interiors, and the Chicago Cultural Center. Each location offers a unique glimpse into Chicago's rich history and artistic heritage.
The tour includes a knowledgeable local guide who provides insights and stories about each location. Gratuities are not included. Prepare to be amazed by the hidden beauty that lies within Chicago's architectural treasures.
Chicago
$85.5
Chicago Art Institute: Skip-the-Line Private Tour
5.0
(271 reviews)
Duration: 150
minutes
Private Art Institute of Chicago Skip-the-Line Guided Tour. This is a special walking tour for people who love art and want to see the best pieces at the Art Institute of Chicago without waiting in long lines. The tour is just for the group and a guide, so it feels personal.
What to Expect: The tour visits famous artworks like 'Paris Street, Rainy Day' and 'Sunday on La Grande Jatte'. People will also see 'Nighthawks' and 'The Old Guitarist'. The guide shares stories about the art and artists. The Art Institute of Chicago is a very big museum with lots of famous art. It has art from all over the world and different times in history.
This private tour lasts for 2.5 hours and includes a professional tour guide just for the group. It also includes all entrance fees. The tour is wheelchair friendly. This tour does not include hotel pickup or drop-off, but the guide suggests using UBER or a taxi. Gratuities (tips) are not included in the price.
Nearby Events
Soldier Field
Aug 21
7:00 PMUsher & Chris Brown R&B Tour at Soldier Field
The R&B Tour starring Usher Raymond & Chris Brown lights up Soldier Field in Chicago with an electrifying showcase of smooth vocals, high-energy choreography, and timeless hits. This dynamic duo, both R&B legends with chart-topping albums and sold-out residencies, promises a night of nostalgic anthems and fresh tracks that have fans buzzing about their unstoppable live chemistry.
Usher Raymond, known for his Super Bowl halftime mastery and Las Vegas residency success, pairs seamlessly with Chris Brown’s acrobatic dance moves and multi-platinum hits like 'No Guidance.' Soldier Field, Chicago’s iconic stadium on the lakefront, hosts massive concerts with stunning acoustics amid its historic columns.
Milwaukee Improv (Main Room)
Sep 17
7:00 PMALOK Live Comedy Show at Milwaukee Improv
ALOK: New Comedy Show at Milwaukee Improv (Main Room) in Brookfield brings Alok Vaid-Menon’s sharp, highly personal comedy to one of the area’s best-known live-comedy rooms. Alok is currently touring in 2026 with a wide run of stand-up and performance dates, and this stop offers audiences a chance to see a bold, contemporary voice in comedy in an intimate club setting.
Alok Vaid-Menon is a comedian, writer, and performance artist known for work centered on gender, identity, and self-expression, blending humor with reflection and audience connection. Milwaukee Improv (Main Room) is designed for close-up comedy, with a room built for strong sightlines and the kind of direct crowd energy that suits a live comedian’s stage presence.
United Center
Aug 05
8:00 PMAriana Grande Tickets Chicago United Center 2026
Ariana Grande's The Eternal Sunshine Tour arrives at Chicago's United Center, delivering a dazzling pop music experience. This highly anticipated 2026 tour supports her seventh studio album, Eternal Sunshine, marking her triumphant return to the stage with a vibrant setlist from both new and classic hits.
The Eternal Sunshine Tour showcases Ariana's iconic vocals and dynamic performance style, combining cinematic visuals with intimate and energetic moments. The United Center, renowned as Chicago's premier arena for top-tier concerts and sporting events, provides an electrifying backdrop for this unforgettable show.
American Family Field
Aug 28
6:40 PMBrewers vs. Rangers: Milwaukee Showdown!
Brewers vs. Rangers at American Family Field: Get ready for an exciting Major League Baseball game as the Milwaukee Brewers take on the Texas Rangers at the iconic American Family Field. This contest will feature a thrilling display of athleticism and tactical maneuvers on the diamond. Expect to witness powerful hitters launching balls into the stands, swift runners stealing bases, and skilled pitchers delivering masterful performances.
American Family Field, the Brewers' home stadium, boasts a distinctive open-air design complemented by a retractable roof, guaranteeing that the game will proceed regardless of weather conditions. The stadium's architecture provides fans with intimate and engaging viewing angles, ensuring an immersive experience. This event is tailored for attendees seeking a relaxed and family-friendly sporting atmosphere, perfect for fans of all ages.
The Chicago Theatre
Sep 26
7:00 PMBassem Youssef: The Belly of the Beast Tour
Bassem Youssef: The Belly of the Beast Tour brings the Egyptian-American comedian and satirist to The Chicago Theatre for an evening of sharp political commentary and observational humor. Known globally as the "Egyptian Jon Stewart," Youssef has captivated audiences worldwide with his fearless approach to comedy that blends social critique with intelligent wit. This tour marks his continued expansion into English-language stand-up, where he applies the same uncompromising satirical lens that once drew 40 million weekly viewers to his groundbreaking television show.
Youssef's journey from cardiac surgeon to internationally acclaimed satirist has made him one of the most influential comedians of his generation. His ability to tackle complex political and social issues with humor has earned him recognition as one of Time magazine's 100 most influential people. The Chicago Theatre, one of America's most iconic performance venues, provides the perfect backdrop for an artist who has spent his career challenging authority and sparking meaningful conversation through comedy.
Rosemont Theatre
Mar 12
7:00 PMLetterkenny Live Tickets at Rosemont Theatre
Puppers Presents Letterkenny Live at Rosemont Theatre brings the hit comedy universe to the stage with an all-new original live show built around the sharp banter, character-driven humor, and small-town chaos fans know from the series. The 2027 North American tour is billed as a 90-minute live experience and features cast members including Jared Keeso and Nathan Dales, making this one of the most anticipated Letterkenny events of the year.
Letterkenny has become a breakout comedy phenomenon through its long-running TV run, specials, live tours, and loyal fan base, and this production extends that momentum with fresh sketches and live performance energy. Rosemont Theatre is a major Chicago-area venue known for hosting large-scale concerts and theatrical events, giving this comedy night a polished setting with strong sightlines and a convenient suburban location.
Chicago Best Things to Do: Concerts, Helicopter & Food Tours
The Chicago skyline is hiding a secret- a ton of them, actually. It’s more than a view: it’s got adventures you're meant to explore. Breathe in the winds and excitement of a helicopter tour, party at top concerts, or dive into food and pizza tours. Walk beside history on a gangster mob tour, take a fireboat or bus tour. Looking to get wild tonight? Find events going on sooner than tomorrow, from EDM to country concerts. Check all your bucket list boxes, and live stories you’ll remember forever.
View Chicago Activities