Fang-tastic! Hit 3 Halloween pet costume contests in one day

Howl-O-Ween is creeping up, and Chicago is buzzing with BOO-tiful events! But nothing is more fang-tastic than pets in costume. We’ve rounded up our top three pet costume contests, all happening on the same day—perfectly timed so you can take your dog, cat or even iguana to all three spooky showdowns!

 38th Annual Streeterville Dog Halloween Party- 9- 11 a.m., MCA Chicago, Dog Parade at 9:45 a.m

Get ready for paws, prizes and plenty of cuteness! On Saturday, October 25, from 9–11 a.m., the Museum of Contemporary Art Chicago hosts its 38th Annual Streeterville Dog Halloween Party along the museum’s Lake Shore Park side. This free, long-running community favorite invites dogs (and their humans) to strut their stuff in creative costumes during the dog parade at 9:45 a.m., judged by Alderman Brian Hopkins and Maureen Schulman. Every pup gets a prize, and a $10 donation to PAWS Chicago is encouraged to help shelter pets. Guests can bring a dog toy for a fun prize swap, and cat lovers can join virtually by uploading photos to MCA’s Facebook for the Virtual Cat Costume Contest. Leashes (or carriers) required—come early, dress up your pet, and enjoy one of Streeterville’s most charming Halloween traditions!  (visit.mcachicago.org)

Robert’s Pizza & Dough Company Presents: Howl-O-Ween 2025, Sat. Oct. 25, 2-4 p.m.

Celebrate Halloween with your four-legged friend at Robert’s Pizza & Dough Company’s fifth annual Howl-O-Ween event on Saturday, October 25, from 2–4 p.m. Located at 465 N McClurg Ct, Chicago, IL, this festive gathering invites all dog owners to join in a delightful afternoon of costume fun and community spirit. Costume Categories: Compete in three categories—Scariest, Cutest, and Most Creative. Humans are encouraged to join the fun and participate as well! Prizes: Winners will receive exciting prizes, including gift baskets filled with dog goodies, Robert’s gift cards, and more. On-Site Photographer: Capture the moment with professional photos to cherish for years to come. Treats & Drinks: Enjoy dog treats for your pets and Halloween-themed cocktails for the humans. This event is free to attend, making it an accessible and enjoyable outing for all pet lovers. Whether you're a local or visiting Chicago, Howl-O-Ween at Robert’s Pizza & Dough Company promises a memorable experience for both you and your canine companion. (For more information and to RSVP, visit Robert’s Pizza & Dough Company Events)

Howl-O-Ween Pet Costume Contest at Harry Caray’s Tavern, Oct. 25 from 3:45- 5 p.m.

It’s time to dress up your furry (or scaly!) friend for some Halloween fun on Friday, October 25, from 3:45–5 p.m., at Harry Caray’s Tavern on Navy Pier. The annual Howl-O-Ween Pet Costume Contest, benefiting PAWS Chicago, welcomes pets of all kinds to strut their stuff in a festive, family-friendly competition.Participants can vie for prizes in categories including Most Creative, Cutest, Spookiest, Best Ensemble or Pair (human/pet or pet group), and the coveted Grand Prize “Best in Show.”Top winners will take home exciting prizes, including a pair of tickets for a dog-friendly ride on the SeaDog speedboat, courtesy of City Cruises.So grab your leash (or carrier), get your costumes ready, and join the Navy Pier crowd for a tail-wagging afternoon of Halloween spirit—all for a great cause! (navypier.org)

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