Birthday Party at NAIA, Chicago

A 50th birthday brought friends and family to NAIA, a riverside restaurant in downtown Chicago, on August 29, 2026. The guest list mixed longtime friends with newer ones, and everyone dressed for the occasion, which made for good material at the sketching table.

One artist worked the party and drew 53 portraits over the evening. Our host took a quick photo of each guest, about twenty seconds, and sent them back to the party; the artist drew from the photo, and a text let each guest know when their sketch was ready to pick up at the table, signed and in a protective sleeve.

The setting did a lot of the work. The restaurant looks out over the Chicago River, the late-summer air was warm, and the city skyline was in view the whole night. Spirits stayed high from the first arrivals through the last portrait.