The Most Fun You’ll Have Clothed: Paint & Sip Chicago Edition

Host an unforgettable night of wine, laughter, and life drawing — with a gorgeous male model as your muse.

Looking for a paint and sip Chicago with male model experience that goes beyond the usual? Red Hot Annie offers the most unforgettable girls’ night out in Chicago — blending cheeky fun, artistic flair, and a whole lot of eye candy. Whether you’re planning a bachelorette party, birthday bash, or just need an excuse to let loose, this is your sign to book a night your guests will never forget.

Book a Paint & Sip Chicago

Click to see available times — reserve your session in just a few clicks.

How to Book a Chicago Paint & Sip Event

Submit Your Request: Fill out the form below or email me directly at annie@redhotannie.com.

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💋 What’s Included in Your Paint & Sip Party?

✨ A Sexy, Professional Male Model

Tastefully posed and trained for artistic sessions — whether you prefer a suit-and-tie striptease or a classic figure model, we’ll match the energy of your event.

🍷 BYOB or Custom Cocktail Options

You bring the wine, we’ll bring the easels. Want to make it extra? We can arrange specialty cocktails, glasses, or custom drink signage to fit your theme.

🎨 All Art Materials Provided

We supply everything you need to sketch your muse: paper, charcoal, easels, and even a few extra boas if the inspiration strikes.

🪩 Burlesque-Style Vibes

Led by Red Hot Annie — Chicago’s burlesque legend — the event blends sensuality, humor, and empowerment. No experience required. Just good vibes and great company.

🎉 Perfect For…

• 💍 Bachelorette Parties
• 🥳 Milestone Birthdays (30, 40, 50… we see you)
• 🧘 Divine Feminine Circles & Self-Love Rituals
• 👯‍♀️ Girls’ Night Out
• 💔 Divorce Parties (yes, this is a thing — and it’s fabulous)
• 🏢 Corporate Events (fun, classy, unforgettable)

📍 Where Can You Host?

Our paint and sip Chicago with male model events are fully mobile or hosted at one of our trusted partner venues. We travel throughout:

• Downtown Chicago
• Wicker Park & Logan Square
• Oak Park
• Evanston
• Private residences and rentals

Have a venue in mind? Let’s make it work.

🖌️ Why Paint With Red Hot Annie?

Red Hot Annie isn’t just a performer — she’s a vibe curator. With over a decade of experience producing burlesque, empowerment workshops, and creative events for women, her signature paint night format is bold, body-positive, and joy-fueled.

This isn’t your average wine-and-canvas setup.
It’s a sensual celebration of creativity and womanhood — with a sexy twist.

💌 How to Book Your Paint and Sip

1. Choose your vibe. (Wild? Classy? Divine feminine?)
2. Pick your date and group size (5 to 30 guests)
3. We send you a quote and plan the perfect package
4. You show up, sip, and sketch. (Or scream-laugh. That’s fine too.)

🖤 Testimonials

“We booked this for my sister’s bachelorette and ended up howling with laughter and awe. The model was HOT and so respectful.”
– Dana L.

“Annie’s energy made everyone feel at ease. It was sexy, but also empowering and totally classy.”
– Rachel M.

redhotannie

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