When: Sat, Oct 24, 2026 at See event link
Where: Chicago's First Lady Cruises, 112 E. Wacker Dr, Chicago, IL 60601
Category: Venue Event · Pet attendance: Dogs welcome (per venue listing, not organizer-confirmed) · Price: From $46 general boarding
Chicago's First Lady 2026 Howl-O-Ween Canine Cruise. Bring your pup in costume for a 90-minute Chicago River and Lake Michigan cruise with narrated city highlights, pumpkin-flavored dog treats, and prizes for best-dressed dogs. Costume contest winners are entered to win a $1,000 donation made by First Lady in the winner's name to a pre-screened canine organization. The organizer page states the cruise sails Saturdays and Sundays, October 17-18 and 24-25, 2026, with tickets from $46 general boarding. UNCONFIRMED: the organizer page does not publish departure times for this cruise; the time must be confirmed on the booking page before publishing. Source: https://firstlady.com/cruises/howl-o-ween-canine