Chicago Is Hosting a Halloween Cruise for Dogs, and Yes, There’s a Costume Contest

CHICAGO— Halloween costumes, Chicago skyline views and a boat full of dogs.

That is essentially the plan for this weekend.

The Howl-O-Ween Canine Cruise returns for its final weekend of 2026 on Saturday, October 24 and Sunday, October 25, taking dogs and their humans on a 90-minute cruise along the Chicago River and Lake Michigan aboard Chicago’s First Lady Cruises. Tickets for humans start at $46.

And yes, dogs are encouraged to come dressed for Halloween.

The cruise includes pumpkin-flavored dog treats, a canine costume contest and prizes for some of the best-dressed pups, making this one of the more unusual ways to experience Downtown Chicago during Halloween season.

What Happens on a Halloween Cruise for Dogs?

The Howl-O-Ween trip starts like Chicago’s regular Canine Cruise, with dogs joining their owners for sightseeing along the city’s waterways.

The boats depart from Chicago’s First Lady Cruises at 112 E. Wacker Drive, along the Chicago Riverwalk near Michigan Avenue. During the 90-minute trip, a guide shares stories about Chicago’s history while the boat travels between the river and Lake Michigan, giving passengers views of the Downtown skyline from the water. Chicago’s First Lady Cruises lists the Halloween sailings for October 17-18 and October 24-25, making this weekend the last chance to catch the 2026 version.

The difference during Halloween is what happens on deck.

Dogs can arrive in costume, humans are welcome to dress up too, and the cruise adds pumpkin dog treats and a costume competition to the regular sightseeing experience. Winners from the costume contests are entered for a grand prize involving a $1,000 donation from First Lady in the winner’s name to a pre-screened canine organization.

So this is not simply a boat that happens to allow pets.

The dogs are the event.

What Dog Owners Should Know Before Boarding

First Lady’s regular Canine Cruises welcome dogs both big and small, but owners should keep their pets on a leash. The boats also provide water bowls, an open-air upper deck and general-admission seating. Outdoor seating is guaranteed, while a full-service bar and small snacks are available for the humans onboard.

First Lady recommends having the entire group at the dock 30 minutes before departure. Cruises operate rain or shine, so late-October weather is worth checking before you leave home, especially since the outdoor deck is a major part of the experience.

Tickets for human passengers start at $46, while First Lady says dogs are $12 each on its Canine Cruises. Children under four ride free. Because seasonal sailings can sell out, checking current availability before heading Downtown is a good idea.

The boarding location is 112 E. Wacker Drive, and discounted parking is available nearby at 111 E. Wacker Drive with validation from the First Lady ticket office.

The Chicago River Makes This More Than a Dog Event

The costumes will probably get most of the photos, but the setting is a big part of why this works.

From the river, passengers get a perspective of Downtown that feels completely different from walking Michigan Avenue. Towers rise directly from the riverbanks, bridges frame the skyline and the boat eventually connects with Lake Michigan through the Chicago Harbor Lock.

For Downtown residents, the cruise also highlights something easy to overlook when talking about city living: Chicago has become increasingly accommodating to people whose weekend plans include their dogs.

Riverwalk outings, patios, parks and seasonal pet events can become part of everyday neighborhood life rather than activities that require driving to the suburbs.

And this weekend is particularly busy for dog owners. Other pet-focused Halloween events are happening around Chicago on October 24 and 25, from costume contests to neighborhood gatherings, giving residents plenty of options if their dog would rather stay on dry land.

Why Events Like This Are Part of Downtown Chicago Living

A dog Halloween cruise may sound like a novelty, and it absolutely is.

But it also says something about the lifestyle surrounding Downtown Chicago.

Someone living in River North, Streeterville, the Loop or Lakeshore East can walk out the door and find river cruises, parks, restaurants, public spaces and seasonal events concentrated within a relatively small area.

For a pet owner, those details can matter when choosing where to live.

A condo building may have a dog run. Another might sit within easier walking distance of the Riverwalk. Some buildings have size or breed restrictions, while others provide dedicated pet amenities or easy access to nearby green space.

That is why buyers with dogs should look beyond whether the listing simply says “pets allowed.”

Ask about building rules, nearby parks, elevator access, outdoor space and what everyday walks would actually look like.

Because if your dog is part of the household, the neighborhood has to work for them too.

Know Before You Go

The Howl-O-Ween Canine Cruise sails Saturday, October 24 and Sunday, October 25 aboard Chicago’s First Lady Cruises at 112 E. Wacker Drive.

The cruise lasts 90 minutes, tickets for humans start at $46, dogs are welcome onboard, and costumes are encouraged for both pets and people.

Bring a leash, arrive early and check current sailing availability before heading Downtown.

And if your dog has ever needed an excuse to dress like a hot dog, pumpkin, superhero or Chicago sports fan, this is probably it.

Looking for a Chicago Home That Works for You and Your Dog?

Pet-friendly living involves more than finding a building that allows animals.

The Cory Tanzer Group at Option Premier helps buyers and renters compare building pet policies, outdoor space, neighborhood walkability, nearby parks and everyday amenities when choosing a home across Chicago.

Because the right neighborhood should work for every member of the household, including the four-legged ones.

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