Known for hosting the best burlesque classes in Chicago, Red Hot Annie now brings you the city’s most unforgettable Paint & Sip with Male Model experience. Whether you’re planning a glamorous bachelorette party in Chicago, a milestone birthday, or a one-of-a-kind girls’ night out, this private sip and paint party delivers laughter, creativity, and a cheeky twist you won’t find anywhere else.

Bride-to-be and friends celebrating a Chicago bachelorette party with a cheeky paint and sip featuring a live male model.

Burlesque & Paint & Sip Bachelorette Party Ideas in Chicago

Why settle for the same old bachelorette routine? Our Paint & Sip Chicago parties add a cheeky burlesque-inspired twist — complete with a live male model, empowering vibes, and just enough sass to make the bride blush.

✨ Professional male models, trained for artistic posing
✨ All materials included (paper, easels, charcoal, props)
✨ BYOB wine or custom cocktails available
✨ Hosted in your home, rental, or one of our Chicago partner venues

Your girls get the joy of creating art, sipping wine, and laughing until your cheeks hurt — all in a safe, classy, female-owned space.

Women enjoying a luxury paint and sip class in Chicago with a male model and wine in an upscale studio hosted by Red Hot Annie.

Unique Girls’ Night Out: Sip and Paint Chicago Parties

Forget dinner and a movie. A Paint & Sip girls’ night out in Chicago is part laughter, part art class, part celebration.

Perfect for:

Girls’ nights out with friends who want something bold
Divorce parties with a “new chapter” toast
Self-love circles & divine feminine rituals
A just-because night of fun and creativity

With Red Hot Annie curating the vibes, you’ll feel empowered, entertained, and completely in your element.

Group of women painting and sipping wine at The Velvet Key Paint & Sip in Chicago hosted by Red Hot Annie.

Male Model Paint & Sip Chicago for Birthdays & Bachelorettes

Celebrate your milestones in style. Whether it’s the big 3-0, 4-0, or 5-0, our Paint & Sip parties turn birthdays into glamorous, unforgettable nights.

🎉 Private parties for groups of 5–30 guests
🎂 Customized themes: classy, cheeky, or full-on wild
📍 Flexible locations: Downtown, Logan Square, Oak Park, Evanston, River North

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

Ready to Book Your Paint & Sip Chicago Party?

Your guest of honor deserves more than a bar crawl—she deserves a night she’ll never forget.

👉 Book Your Luxury Chicago Paint & Sip Package Now