WINTER WONDERFEST 2026/27 Caricature & Face Painting Positions

FACES IN FOCUS is hiring and training for free caricature artists and face painters to help us with our month-long extremely lucrative Winter Wonder Fest Holiday Festival which runs this year from Thanksgiving weekend to January 3rd of 2027 in the back of Navy Pier upstairs in FESTIVAL HALL. At our downstairs booth we pay 35 %, upstairs at WWF 40 %. Please give us your availability. We pay within 5 business days of receipt of invoice. Invoices are to cover the first 15 days and the last 15 plus days of each month. This is the most lucrative time at Navy Pier because it is the most advertised winter spectacle in Chicago. You will not regret it!