Howl-O-Ween Canine Cruise with First Lady

A dog costume contest on a boat

Chicago's First Lady Cruises runs a Howl-O-Ween Canine Cruise: 90 minutes on the river and the lake with a guided city tour, for dogs in costume and the people with them. It sails on four days in 2026 — Saturday and Sunday 17–18 October and 24–25 October.

What First Lady publishes:

• Prizes for the best-dressed dogs, and every costume winner goes into a drawing for the grand prize.
• The grand prize is a $1,000 donation from First Lady to One Tail at a Time, made in the winner's name. The money goes to a Chicago rescue listed in this directory, not to a prize table.
• Pumpkin-flavoured dog treats and water bowls on board.
• Tickets from $46 for general boarding.

What is not published

Departure times. The cruise page lists the dates but not the sailings. Pick a time on First Lady's booking page.

Dog rules. Nothing on the page covers leashes, size limits, how many dogs per ticket, or vaccinations. On a boat with other people's dogs in costume, ask before you book if your dog is reactive or very large.

Getting there

The dock is on the Riverwalk below 112 E Wacker Drive. First Lady asks you to arrive 30 minutes before departure; general boarding opens 15 minutes before. It publishes discounted parking at 111 E Wacker with ticket-office validation. The Riverwalk has no elevators — First Lady points to an ADA ramp at State Street and Wacker, inside Vietnam Memorial Park, offers early boarding for guests with limited mobility, and has a vehicle drop-off on Lower Wacker.

Dogs must be leashed everywhere in Chicago outside a fenced Dog Friendly Area, the Riverwalk included. See Events and Meetups for the rest of the calendar.

Provenance

Dates, length, price, prizes, donation, treats, boarding and accessibility from First Lady's own cruise page, read 14 October 2026, which states the 2026 dates. The listing retires itself after the last sailing.

Lost dog? Chicago Animal Care and Control at 2741 S Western is the city's open-admission shelter and the first place to look.