Dog Events in Crestwood, IL

This dog-friendly wine tasting event features a curated flight of international wines from Louis Glunz Wine, with guests guided through a structured tasting experience exploring different regions, flavors and styles. While humans sip and socialize, dogs can play and mingle in the supervised off-leash park, making it a fun midweek outing for both wine lovers and their pups.

Bring Fido to this annual event—a one-mile walk and vendor fair that raises much-needed funds for animals in need. The vendor fair will feature pet-friendly booths with games, food, entertainment, contests and more!

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.

Leashed dogs are welcome to join this family-friendly 5K walk and charity run! Participants can enjoy a morning of movement and community with live music, food trucks, sweet treats, balloon twisting, and an animal artist. Strollers are also welcome, making this a fun event for the whole family.

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.

This dog-friendly Halloween celebration invites pets to show off their best costumes during a festive costume walk. Guests can enjoy raffles, treats and refreshments, photo opportunities and spooky fun for the whole family.

This dog-friendly Halloween 5K features a scenic paved route and supports K9s for Veterans. Registration includes a short-sleeve T-shirt, finisher medal, doggie finisher medallion, chip-timed race bib, live results and finish-line treats for both humans and dogs.

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.