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!
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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!
Listed by Chicago Loop Alliance · last updated today