The Ultimate Guide to Dog-Friendly Events in Chicago – September 2025
Chicago’s September calendar is full of tail-wagging fun for pups and their people! From scenic runs to craft beer markets, speed dating for dog lovers, and one-of-a-kind races for tiny dogs, there’s an event for every canine enthusiast. Whether you’re a local pet parent or just visiting the Windy City with your furry friend, here are the top dog-friendly events in Chicago this September 2025 you won’t want to miss.
Speed Dating for Dog Lovers (Ages 25–35)
If your ideal first date involves swapping dog stories, sharing training tips, and comparing cute pup photos, this event is for you. Hosted by Meet IRL x Bosly’s, this speed dating night is exclusively for singles aged 25–35—and yes, your dog can come too. You’ll meet a series of like-minded singles in quick, fun rounds, with plenty of doggy charm to keep conversations flowing. It’s the perfect blend of romance, socializing, and puppy playtime.
Date & Time: Thursday, September 4, 2025 | 6:30 PM – 8:30 PM
Location: Bosly's Backyard - 4011 North Ravenswood Avenue #108 Chicago, IL 60613 United States
Tickets: Speed Dating for Dog Lover
Great American Dog Show
Step into the world of top-tier canine competition at the Great American Dog Show. This prestigious three-day event at Cantigny Park is a must for dog enthusiasts of all ages. Watch skilled dogs showcase their talents in conformation, agility, and obedience trials, and stroll through vendor booths offering unique dog products and services. It’s also a great chance to meet breeders and trainers, learn about different breeds, and get inspired by the incredible bond between handlers and their dogs.
Date & Time: Friday–Sunday, September 5–7, 2025 | 8:00am - 5:00pm
Location: Cantigny Park, 1S151 Winfield Road, Wheaton, IL 60189
Tickets: Great American Dog Show
Tails on the Trails for Rescue
If your pup loves a good nature walk, head to the Morton Arboretum for this special fundraising event benefiting animal rescue organizations. Explore scenic hiking trails, take on agility courses, and browse pet-friendly vendor booths surrounded by lush greenery. This event offers a peaceful escape from the city while giving back to a great cause. Dogs must be leashed, but their tails will wag with every step.
Date & Time: Sunday, September 7, 2025 | 9:00 AM – 4:00 PM
Location: Morton Adventure Woods, Lisle, IL
Ticket: Tails on the Trails
Pup Social’s September Dog-Friendly Lineup
Pup Social has a full lineup of fun for pups and their people — from pajama movie nights to trivia, cocktails, and even puppy yoga. Whether you’re a member or a guest, these are the ulti-mutt activities to enjoy with your four-legged best friend.
Muttflix & Chill
Date and Time: Thursday, September 11th | 7–9 PM
Admission: $10 Members | $29 Non-Members
Grab your comfiest pajamas and your pup’s favorite blanket for one of Chicago’s coziest dog-friendly events. A cozy pajama movie night with your pup, complete with dog- and people-safe popcorn and plenty of chill vibes.
Open House Playtime
Date and Time: Sunday, September 21st | 12–2 PM & 4–6 PM
Admission: Free for Members | $34 Non-Members
Enjoy off-leash play, tours, pup cups, and agility fun while discovering everything Pup Social has to offer. Bonus: sign up for a membership during the event and receive a $50 bar + retail credit. This is one of the best dog-friendly activities in Chicago for pups who love to socialize.
Wag Tail Trivia – Test Your Pup Knowledge
Date and Time: Wednesday, September 24th | 4–6 PM
Admission: Free for Members | $10 Non-Members
Think you know everything about dogs? From famous movie pups to quirky breed facts, Wag Tail Trivia will challenge your knowledge while you enjoy drinks, laughs, and friendly competition. Bring your friends (human and furry) for a dog-friendly game night filled with prizes and plenty of tail wags
Pawsh Nights – A Stylish Dog-Friendly Evening
Date and Time: Saturday, September 27th | 4–8 PM
Admission: $10 Members
Looking for a chic dog-friendly night out in Chicago? Pup Social is rolling out the red carpet for an evening of cocktails, shopping, and community. Sip cocktails, shop curated vendors, and enjoy giveaways during this chic night out with your pup. Not a member? Join our pack today!
Puppy Yoga + Barkfest Club – Flow, Feast & Fun
Date and Time: Sunday, September 28th | 8–9 AM Yoga | 9–11 AM Barkfest Club
Admission: $20 Members | $34 Non-Members
Start with a playful yoga class surrounded by adoptable pups, then stay for an 80’s-inspired breakfast party with donuts, mimosas, and agility play. With agility play for pups and tunes from The Breakfast Club era, it’s one of Chicago’s most unique dog events this fall.
Experience Chicago’s skyline like never before aboard the Cruise with Roo—a dog-friendly boat tour that welcomes pups of all sizes. Spend two hours enjoying lake breezes and postcard-perfect views while your dog lounges at your feet or mingles with other furry passengers. It’s a unique way to sightsee and socialize in one relaxing trip.
Date & Time: Sunday, September 7, 2025 | 11:00 AM – 1:00 PM
Location: 112 E Wacker Dr, Chicago, IL 60601, United States
Ticket: Cruise with Roo
Tiny Dog 500
It’s small dogs. It’s racing. And it’s adorable beyond words. The Tiny Dog 500, hosted by Peanut and One Tail at a Time, brings together pint-sized pups for a friendly dash toward the finish line. Expect costumes, cheering crowds, delicious food, and plenty of photo ops. Whether you’re there to race your dog or simply watch, it’s guaranteed to be a good time.
Date & Time: Sunday, September 7, 2025 | 1:00 PM – 4:00 PM
Location: 112 E Wacker Dr, Chicago, IL 60601, United States
Ticket: Tiny Dog 500
PAWS Chicago 5K Walk/Run
Start your Saturday with a burst of energy and a burst of goodwill. The PAWS Chicago 5K Walk/Run for Their Lives takes you along the scenic lakefront while raising funds to support one of Chicago’s largest no-kill animal shelters. Participants include runners, walkers, and plenty of dogs, all there to make a difference for homeless pets. Stick around after the race for a celebration with vendors, entertainment, and adoptable dogs ready to find their forever homes.
Date & Time: Saturday, September 13, 2025 | 7:30 AM – 11:00 AM
Location: Lakeshore Path, Chicago
Ticket: PAWS Chicago 5K
Pet Supplies Plus Adoption Event
Whether you’re ready to adopt or just curious, the Pet Supplies Plus Adoption Event in Orland Park is a heartwarming way to spend your morning. Meet adoptable dogs from local rescues, chat with volunteers about adoption requirements, and pick up supplies to spoil your own pup. Many attendees come just to offer pets, cuddles, and moral support to the adoptable animals.
Date & Time: Saturday, September 13, 2025 | 10:00 AM – 2:00 PM
Location: Pet Supplies Plus – 9430 W 159th Street, Orland Park, IL
Ticket: Pet Supplies Plus Adoption Event
Dog Friendly Market
Close out your weekend with a relaxed afternoon at the Dog Friendly Market hosted by Chicago Dog Co. This event transforms Midwest Coast Brewing into a hub for pet-focused shopping, tasty treats, and craft beer. Shop from local vendors, find one-of-a-kind accessories for your pup, and let your dog mingle with other canine guests. It’s a laid-back, community-driven event perfect for both humans and dogs.
Date & Time: Sunday, September 21, 20255 | 12:00 PM – 5:00 PM
Location: Pet Supplies Plus – 9430 W 159th Street, Orland Park, IL
Ticket: Dog Friendly Market
Paw-sitively the Best September Yet
From the romance of Speed Dating for Dog Lovers to the excitement of the Tiny Dog 500 and the good vibes of the Dog Friendly Market, Pup Social adds to the lineup with a cozy Muttflix & Chill pajama movie night, playful Open House Playtime sessions, a laugh-filled Wag Tail Trivia game night, the stylish Pawsh Nights cocktail and shopping social, and the ulti-mutt wellness morning with Puppy Yoga + Barkfest Club. With so many dog-friendly events in Chicago, September is the perfect time to explore the city and make memories with your pup. Whether you’re seeking high-energy races, scenic adventures, or cozy community gatherings, there’s something here for you and your pup.
