Dog Events Near Tree Studio Complex, Chicago, IL, US

This dog-friendly Oktoberfest parade invites pups to strut their stuff in festive fall attire, with costumes encouraged but not required. Dogs can compete in small, medium and large breed categories, with prizes awarded to each category winner and Best in Show. Registration is required and space is limited. Meet at the stage on Schiller and Wells for check-in.

Well-behaved dogs are welcome to join their humans aboard a scenic cruise along the Chicago River. Enjoy light snacks, easy entertainment, and beautiful views of the city while supporting the lifesaving work of Chicago Animal Care and Control and its nonprofit Friends. Boarding starts at 5:30 PM and departs at 6 PM.

Dogs are welcome to join guests at this 21+ cider tasting event featuring a wide selection of local, regional, and national ciders. Sample seasonal and traditional styles while enjoying fall flavors and a festive atmosphere, with food available for purchase, including gluten-free options. Tickets include cider tastings and a commemorative tasting glass.

This puppy training workshop teaches the foundational skills young dogs need to become confident, well-mannered companions. Participants will learn essential commands, positive reinforcement techniques, puppy socialization guidance and strategies for addressing common behaviors, with hands-on practice and a Q&A led by a Pup Social trainer. Attendees also receive 15% off future training packages purchased the day of the workshop.

This dog-friendly meetup brings together pet influencers, aspiring creators, photographers and dog lovers for an afternoon of networking, content creation and supervised off-leash play. Attendees can connect with other dog accounts, exchange ideas, capture photos and videos and explore collaboration opportunities. All experience levels are welcome.

Bring Fido to Chicago’s premier pet-friendly black tie gala! Set at the legendary Drake Hotel, guests and their canine companions walk the red carpet, participate in live and silent auctions, and enjoy a dinner buffet and dancing. Four-legged guests will enjoy an evening of indulgences as well, including dinner served in crystal goblets at the dog buffet. Human guests be 21+ to attend the event.

Celebrate the holiday season with your pup and the Live Like Roo Foundation at this dog-friendly Holiday Pet Market featuring local vendors, holiday cocktails and coffee, photos with Santa, caricatures, and festive photo opportunities. Bring your pup to shop, socialize and enjoy a day of seasonal fun with fellow pet lovers.