Howl-O-Ween Canine Cruise

The Howl-O-Ween Canine Cruise invites pet parents to dress up their dogs for a 90-minute river and lake cruise on the Chicago Riverwalk. Running all day Saturdays and Sundays from October 17 to 25, 2026, the event features pumpkin-flavored dog treats, city highlights, and a costume contest with a $1,000 grand prize donation to a canine organization.