Chicago’s top three (cutest) pet Halloween costume contests

Chicago’s Halloween fun isn’t just for humans. On Saturday, October 31, four-legged fashionistas will have their moment in the spotlight as three popular local destinations invite pets and their people to show off their most creative, cute and downright spooky costumes.

From a longtime Streeterville tradition at the Museum of Contemporary Art Chicago to a PAWS Chicago fundraiser at Harry Caray’s Navy Pier and a waterfront Halloween party at Robert’s Pizza & Dough Company, these contests offer plenty of reasons to get those tails wagging. Whether your pet is a pumpkin, a pint-size superhero or a very convincing vampire, there’s a place to strut that stuff.

1. MCA Chicago’s 39th annual Streeterville pet Halloween party

For a Halloween tradition with serious staying power, head to the Museum of Contemporary Art Chicago for the 39th annual Streeterville Dog Halloween Party. This neighborhood favorite welcomes costumed dogs and cats for a morning of adorable outfits, friendly competition and a parade that could give some human fashion shows a run for their money.

The festivities begin at 9 a.m. in the museum’s Anne & John Kern Terrace Garden, with the doggy parade stepping off at 9:30 a.m. Expect plenty of creative interpretations of Halloween classics, from spooky creatures to imaginative pop-culture characters.

The contest will be judged by Ald. Brian Hopkins and Streeterville resident Maureen Schulman, who will award prizes to the best-dressed animals. Organizers also encourage participants to bring a dog toy so every dog can receive a prize.

Admission is free, making this a particularly appealing option for families and anyone who wants to start Halloween with a little four-legged fun. Pets must be leashed, and participants with their animals should enter through the museum’s back gate bordering Lake Shore Park.

Registration and details: MCA Chicago’s official event page. 

2. Harry Caray’s Navy Pier Howl-O-Ween pet costume contest

If your pet enjoys an audience, the annual Howl-O-Ween costume contest at Harry Caray’s Navy Pier is the place to make an entrance. With a lakefront setting, prizes and a good cause at its heart, this Halloween gathering gives pets of all kinds their chance to shine.

The contest, hosted again by 'Candid' Candace Jordan, benefits PAWS Chicago, with all entry fees going to the organization. Dogs, cats and other pets, including feathered and scaly companions, are welcome to compete in five categories judged by Jordan, Danielle Borisy and Grace Fuller: Most Creative, Cutest, Spookiest, Best Ensemble or Pair, and the coveted grand prize, Best in Show.

There will also be a Yappy Hour hosted by Tito’s Handmade Vodka. 

With proceeds supporting animals in need, this is a Halloween outing with a little extra heart. Space is limited, so registering in advance is recommended.

Registration and details: Harry Caray’s Howl-O-Ween at Navy Pier.

3. Robert’s Pizza & Dough Company’s sixth annual Howl-o-Ween

For those who prefer their Halloween festivities with a side of pizza, Robert’s Pizza & Dough Company is hosting its sixth annual Halloween celebration along the Ogden Slip waterfront in Streeterville.

Running from 2 to 4 p.m., the event invites dog owners to bring their costumed companions for a pet parade and contest. Categories include Scariest, Cutest and Most Creative, and the humans aren’t left out: owners can compete, too. So if you and your pup have been plotting a matching costume, this is your opportunity to make it count.

Prizes include gift baskets filled with goodies for pets, Robert’s gift cards and other treats. A photographer will be on-site to capture the costumes, giving owners a keepsake from the afternoon. Dog treats will be available for the four-legged guests, while Halloween cocktails will help the humans get into the spirit.

The waterfront location adds to the appeal. Robert’s is known for its artisanal thin-crust pizzas and outdoor dining along the Ogden Slip, making it a natural spot to turn a costume contest into a longer Halloween outing. Consider sticking around for a meal after the competition.

Registration and details: Robert’s Pizza & Dough Company.

Planning your Halloween pet parade

All three contests take place on Saturday, October 31, so it’s possible to make a full day of pet-friendly Halloween fun, although fitting in all three will require some careful timing.

My advice? Pick a costume your pet can comfortably wear, keep water and treats handy, and remember that the best outfit is one your furry friend can actually enjoy wearing. Whether your companion arrives as a Chicago sports legend, a tiny pumpkin or a four-legged celebrity, October 31 promises plenty of Halloween photo opportunities.