Howl-O-Ween Canine Cruise

Where are the pet parents who count down to dressing up their dog every Halloween? This one’s for you! Our 2026 Howl-O-Ween Canine Cruise is back, setting sail on the second and third weekends of October. 

Bring your pup in costume (humans can join the fun too!) for a 90-minute river and lake cruise featuring city highlights, pumpkin-flavored dog treats, and prizes for the best-dressed dogs. Costume contest winners will be entered to win our grand prize: a $1,000 donation made by First Lady in the winner’s name to one of our pre-screened canine organizations!

Location: 112 E. Wacker Dr., Chicago, IL, 60601