Howl-O-Ween Guide: Chicago Dog Events October 2025
Chicago is one of the most dog-friendly cities in the country, and this October, the city is packed with can’t-miss dog events for pups and their people. From festive Halloween dog costume contests to charity dog fundraisers, there’s no shortage of ways to celebrate the season with your furry friend. Whether you’re searching for a dog-friendly market, a pet adoption fundraiser, or a fun run with dogs, here’s your ultimate Chicago dog events guide for October 2025.
Featured Dog Events in Chicago – October 2025
Barktoberfest 2025! A fundraiser for One Tail at a Time!
Date and Time: Saturday, October 4 · 1 PM – 4 PM CDT
Location: Canine Crews - 1616 N Washtenaw Ave Chicago, IL 60647 United States
Tickets: Eventbrite
Raise a glass for rescue pups! Barktoberfest Chicago 2025 is a seasonal dog-friendly festival benefitting One Tail at a Time, one of Chicago’s top dog rescue organizations. Expect craft beer, raffles, pet vendors, and adoptable dogs, all while supporting an amazing cause.
Bark Bash 2025
Date and Time: Thursday, October 9 · 6 PM – 9 PM CDT
Location: Goose Island Barrel House: 603 N Sacramento Blvd Chicago, IL 60612
Tickets: $125 per person
Chicago Canine Rescue’s annual dog fundraiser gala is back! This elegant evening features food, cocktails, silent auctions, and stories of rescued dogs. If you’re looking for a way to support dog adoption in Chicago, this is a must-attend event.
Pups & Pumpkins
Date and Time: Sunday, October 12 · 3 PM – 5 PM CDT
Location: Clara’s - 6550 Illinois 53 Woodridge, IL 60517 United States
Tickets: Eventbrite
Celebrate autumn with your pup at Pups & Pumpkins Chicago 2025. This festive dog-friendly fall event includes photo ops with pumpkins, treats, and games for dogs and their humans. Perfect for those searching for fall activities with dogs in Chicago.
Dog Friendly Market @ Midwest Coast Brewing
Date and Time: Sunday, October 12 · 12 PM – 5 PM CDT
Location: Midwest Coast Brewing, 2137 W Walnut St, Chicago, IL 60612
Tickets: Eventbrite
If you love shopping and dogs, this Chicago dog-friendly market is a perfect weekend outing. Hosted by Chicago Dog Co., the market features local pet vendors, craft beer, and dog-friendly shopping in the heart of Chicago.
Pup Social’s October Dog-Friendly Lineup
Get ready for Pup Social’s October lineup filled with festive fun, special perks, and tail-wagging experiences! Membership is required for certain Pup Social events.
BARK ‘N’ BOOZE MIXOLOGY CLASS
Date and Time: Thursday, October 16th, 2025 | 5pm-8pm
Admission: $35 Members I $50 Non-Members
Includes 2 signature Halloween cocktails
This Halloween season, Pup Social is turning up the spirits with a cocktail-making night that’s equal parts spooky, social, and dog-friendly! Grab your pup, dress in your best costume, and join us for a guided mixology experience where you’ll learn to shake, stir, and sip your way through two Boo-zy signature cocktails designed just for the occasion.
SPOOKTACULAR PAW-TRAITS
Date and Time: Sunday, October 19th 2025 | 4pm-6pm
Admission: $20/family (Members)
This Halloween, Pup Social members are invited to step in front of the camera for a professional family & pet photoshoot designed to capture the magic of the season. Dress your pup (and yourself!) in your best costumes and strike a pose against our spooky-chic Halloween backdrop. From cobwebs and pumpkins to glowing lanterns, we’ll create the perfect setting for festive portraits you’ll treasure.
HOWL-O-WEEN EXTRAVAGANZA
Date and Time: Sunday, October 26th 2025 | 1 PM – 7 PM | 1:00 PM - 5:00 PM - Open house
Admission: $20/pup (Members) I $35/pup (Non-Members)
Admission is charged per dog. If you’re attending without a pup, there’s no fee.
This year’s Howl-o-ween is all about spooky fun for pups and their people! Guests can enjoy interactive activities, festive photo ops, and exclusive treats designed to make the night unforgettable.
Pumpkin carving station – for humans only
Pumpkin Paw Prints Craft Station – Let your pup get creative! Dogs will dip their paws in safe, washable paint and “stamp” their very own mini pumpkin keepsake.
Raffle & Giveaways – Every guest is automatically entered to win prizes like local vendor gift cards, Pup Social passes, and exclusive swag.
Bubble Cauldron Chase – Watch tails wag as pups dart through a flurry of bubbles set to spooky tunes.
Trick-or-Treat Vendor Trail – Explore booths from local vendors handing out goodies and surprises for both dogs and humans
MUTTFLIX & CHILL: SPOOKY EDITION
Date and Time: Thursday, October 30th 2025 | 6pm-8pm
Admission: $10 Members & Package Holders I $29 Non-Members
Get cozy with your pup and settle in for a Halloween movie night under the stars at Pup Social! Our Muttflix & Chill: Spooky Edition transforms the Pup Park into an outdoor theater, complete with blankets, popcorn, and plenty of pup-friendly treats.
BooPalooza and BarkPalooza
Date and Time: Saturday, October 18, 2025 | 10 AM – 2 PM CDT
Location: Wicker Park, 1425 N Damen Ave, Chicago, IL
Event Info
Join Pup Social at Boo-Palooza, Wicker Park’s annual Halloween festival filled with costumes, community, and canine fun! This family-friendly celebration brings together neighbors, local businesses, and of course—plenty of pups in their spookiest (and cutest) attire. Stop by the Pup Social table to learn more about Chicago’s first and only off-leash social club for dogs and their people. We’ll have treats, giveaways, and info on upcoming events, plus a chance to connect with our growing community of pup lovers.
39th Annual Doggie Halloween
Date: Saturday, October 25th 2025
Time: 9 AM – 1 PM
The 39th Annual Doggy Halloween is back, bringing Chicago’s dog lovers together for a festive parade, creative costume contests, and plenty of seasonal fun for pups and their families. Pup Social is excited to be part of the celebration with our own table—stop by to grab treats, learn more about Chicago’s first luxury off-leash social club, and take advantage of exclusive member perks while enjoying one of the city’s favorite fall traditions.
Howl-O-Ween Party 569 Skinner Park
Date: Sunday, October 26th 2025
Time: 10 AM - 1 PM
Join us for a spooky good time at Skinner Park! Dress up your pup in their best costume and enjoy an afternoon of tricks, treats, and tail wags. This off-site Pup Social event will feature dog-friendly activities, festive photo ops, and plenty of chances for pups (and their people!) to show off their Halloween spirit. From playful games to tasty goodies, it’s the pawfect way to celebrate the season with our community.
Howl-o-ween 5k - Dan Ryan Woods
Date and Time: Sunday, October 26, 2025 | 9:00 am CST
Location: Dan Ryan Woods, 87th St & Western Ave, Chicago, IL 60620
Registration: Sign Up Here
This festive Chicago dog run combines fitness and fun. Dress up with your pup and join other dog lovers for a dog-friendly 5K through the scenic Dan Ryan Woods. Costumes, prizes, and plenty of tail wags guaranteed.
Paint Night: Honor Your Lost Pet (Día de los Muertos)
Date and Time: Tuesday, October 28 | 6:30 PM -8:30 PM CDT
Location: BottlesUp! - 3164 North Broadway Chicago, IL 60657 United States
Tickets: Eventbrite
Celebrate and honor the memory of beloved pets who have passed at this touching pet memorial paint night. Inspired by Día de los Muertos, attendees can create a one-of-a-kind keepsake while sharing stories of their furry friends.
5th Annual Halloween Dog Costume Contest & Cupcake Truck
Date and Time: Thursday, October 30 · 5:30 - 7:30pm CDT
Location: 849 North Franklin Street Chicago, IL 60610 United States
Tickets: Eventbrite
Get your pup ready for one of the best Halloween dog events in Chicago! This contest is all about creativity, with prizes for the best costumes and a cupcake truck for humans. This event is a highlight for anyone searching for dog Halloween parties Chicago 2025.
Haunted Howl-o-ween Party – Wag Hotels
Date and Time: Thursday, October 30th | 6:30 PM - 8:00 PM
Location: Wag Hotels Chicago, 1214 W Monroe St, Chicago, IL 60607
Tickets: Wag Hotels Event Page
Wag Hotels’ annual Haunted Howl-o-ween Party is one of the most popular dog costume parties in Chicago. Expect a pet costume contest, trick-or-treating for dogs, spooky photo booths, and dog treats galore.
Paws-itively Spooktacular Wrap-Up!
Chicago is going all out for Howl-O-Ween 2025! From parades at Belmont Harbor to spooky 5Ks, pumpkin-filled markets, Pupsocial’s Spooky Lineup, and over-the-top costume contests, this October is a dream come true for pups and their people.
So grab your leash, dress up your four-legged bestie, and get ready to make memories all month long. Whether you’re shopping local, sipping craft brews, or strutting down a parade route, one thing’s for sure—Chicago dogs know how to party. Don’t miss a single wag, woof, or wag-tastic photo op this Halloween season!
