Art Instructor – Paint and Sip Studio Chicago Sip & Paint​/class

Paint & Sip Instructor

Chicago Sip & Paint is a vibrant paint and sip studio offering fun, instructor-guided painting experiences. We host public classes, private celebrations, kids’ events, and corporate/team-building events both in our studio and at offsite locations.

Our studio is BYOB, and adult guests are welcome to bring their favorite drinks and snacks to enjoy while they paint. Our events combine step-by-step painting instruction with music, drinks, and a relaxed, social atmosphere.

Classes are beginner-friendly and focused just as much on creating a fun, memorable experience as creating a great painting.

We are looking for an outgoing, dependable Paint & Sip Instructor to lead in-studio classes as well as private and corporate events throughout the Chicago area.

This role is ideal for someone who has an art background but also genuinely enjoys working with people. We’re looking for someone who can confidently lead an event from setup through cleanup while creating a fun, welcoming, and organized experience for our guests.

The position will initially average 1–3 events per week, depending on bookings, availability, and performance, with opportunities for additional events and increased responsibility over time.

• Arrive approximately 1 hour before in-studio events to prepare the space, canvases, paint, brushes, and other supplies
• Lead guests through a painting in a clear, engaging, step-by-step format
• Create a fun, upbeat, and welcoming atmosphere throughout the event
• Adapt your teaching style and energy to different groups, including public classes, private parties, corporate groups, and occasional kids’ events
• Keep classes moving at an appropriate pace while providing individual guidance to guests as needed
• Complete post-event cleanup, organization, and resetting of the studio or event space
• For offsite events, handle assigned event logistics, which may include loading/unloading, transporting, setting up, packing, and returning supplies to studio. Be able to lift 20-30lbs.
• Represent Chicago Sip & Paint professionally and provide an excellent guest experience from beginning to end

• Wednesday–Friday evenings
• Saturday and Sunday afternoons and evenings
• We also host corporate and private events that may take place during weekday daytime or evening hours.

Weekend availability is important for this position, with flexibility to take on occasional weekday events preferred. You are not expected to be available for every event or every listed time period.

Schedules may vary from week to week based on event bookings and your availability.

In-studio classes typically run 2.5–3 hours, with approximately 4–4.5 hours total on-site time including setup and cleanup.

Total time for an offsite event depends on the location, event length, group size, setup requirements, and transportation. Instructors will be trained on our offsite event process before being expected to lead these events independently.

Offsite events take place at corporate offices and event venues throughout the Chicago area.

A personal vehicle is not required for this position. Depending on the event, instructors may meet the team directly at the venue or be responsible for transporting event supplies from our studio when running the event independently. When an instructor is responsible for transporting supplies, rideshare transportation costs are covered by Chicago Sip & Paint.

Lead Instructor: $100+ per event + tips

Standard in-studio events typically require approximately 4–4.5 hours total, including setup, instruction, and cleanup.

Compensation for offsite events can vary based on the total time commitment, event length,…