Art Instructor – Paint and Sip Studio Chicago Sip & Paint $100/class

Chicago Artists Coalition; Chicago, Northern (IL, KY); Hybrid; USD 5,200 - 16,000; Full time

Job summary

Chicago Sip & Paint is seeking an outgoing Paint & Sip Instructor to lead in-studio classes and private/corporate events throughout the Chicago area. Candidates should have an art background and enjoy working with people, guiding guests from setup to cleanup while creating a welcoming and organized experience.

The role typically averages 1–3 events per week, with potential for additional events and more responsibility over time. Must be able to lift 20–30lbs and work weekends.

Qualifications

• Experience with acrylic painting.
• Comfortable speaking, teaching, and engaging with groups.
• Friendly, outgoing, patient, and confident personality.
• Strong communication and customer-service skills.

Responsibilities

• Arrive ~1 hour before events to prepare space and supplies.
• Lead guests through step-by-step painting instruction.
• Create a fun, upbeat, welcoming atmosphere.
• Adapt teaching style to different groups (public, private, corporate, kids).
• Keep classes moving at a good pace with individual guidance.
• Post-event cleanup and space resetting.

Skills

Acrylic painting

Public speaking

Customer-service

Organized

Reliable

Job description

Paint & Sip Instructor

About Us

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.

Position Overview

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.

Responsibilities

• 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

Schedule & Availability

• 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.

Time Commitment

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 & Transportation

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.

Compensation

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, location, and logistical responsibilities. Additional compensation is provided for events that require more time or responsibilities than a standard event.

Event Assistant: $20/hour + applicable tips

For select events, team members may also be offered shifts in a supporting Event Assistant role rather than as the lead instructor. Event Assistants help with event preparation, setup, guest support during the class, cleanup, packing, loading/unloading, and other event-related tasks. The Lead Instructor is responsible for teaching the event.

Opportunities for additional events, increased pay, and expanded responsibilities may be available based on experience, reliability, availability, and performance.

Requirements

• Experience with acrylic painting and a strong foundation in art
• Comfortable speaking, teaching, and engaging with groups
• Friendly, outgoing, patient, and confident personality
• Strong communication and customer-service skills
• Reliable, punctual, organized, and professional
• Comfortable working independently and taking responsibility for assigned events
• Ability to follow an established painting and teach it in an approachable, beginner-friendly way
• Weekend availability, with some weekday flexibility
• Ability to lift, carry, load, and unload event supplies and equipment