Chicagoland Dog-Friendly Events
December 2025 — Festive Fun for You and Your Furry Friend! 🎄🐾
The holiday season is here, and Chicago is rolling out the red carpet for our four-legged friends! From Santa photo ops to ugly sweater parties, there's no shortage of ways to celebrate with your pup. Grab your leash, bundle up, and make some tail-wagging memories!
Please note: These are not Training That Lasts events. We're sharing this information because we strongly encourage connection and structured socialization for you and your dog. Exploring new environments together, practicing calm behavior around distractions, and building positive experiences are all part of strengthening your bond and reinforcing the training work you do at home.
Early December Festivities
Bundle up for a magical winter wonderland walk! The Morton Arboretum opens its stunning Illumination: Tree Lights show to leashed dogs on these special Wednesday nights. Also check out Dog Admission Days on Dec 3, 10, 14, 17 and 28.
A festive dog-centric fundraiser benefiting Live Like Roo! Local vendors, holiday cocktails, treats, and an award-winning pet photographer. Bring your best holiday spirit — and your ugliest sweater!
Dress your pup in festive attire for a professional holiday portrait with Santa! You'll receive a professionally edited digital photo. Space is limited — reserve online.
Chicago French Bulldog Rescue throws a yuletide bash! Best Dressed pup contest, silent auction, raffles, and $2 beer specials. First 150 guests get a free doggie swag bag!
FREE holiday photos with Santa Paws! Snap pics on your phone, sample a free "Puppermint Mocha" treat, and enter the Santa Howliday Raffle. Perfect for last-minute Christmas cards!
Get a festive family portrait with Santa while supporting a shelter! All well-behaved, pet-friendly dogs (and cats in carriers) welcome. Drop-in style — no reservation required.
Snap adorable pics at this indoor dog-training gym turned photo studio! A laid-back session where dogs can be themselves — whether mugging for camera or sniffing Santa's boots.
Calling all doodles and doggos! Watch the Toys for Tots Motorcycle Parade while your pup plays off-leash. Santa for photos, winter wonderland backdrop, games, giveaways, and treat stations!
Capture the Festival of Lights with Fido! Professional pet photo sessions with both Hanukkah and Christmas themed sets. Each ~15 min session includes 5 edited photos.
This posh pet boutique transforms into a sparkly winter wonderland photo studio! Professional photographer, frosty decorations, twinkling lights. All breeds and sizes welcome.
Mid-December Magic
Two nights of ugly sweater fun! Dec 11 is for tiny tots (under 20 lbs) and Dec 12 for big pups (20+ lbs). Intimate cozy parties with pup-safe eggnog, holiday cookies, and photo backdrops.
Shop 20+ small businesses at this indoor-outdoor market! Gifts for dogs and humans, holiday cocktails/mocktails, festive photo backdrops, plus access to the warm off-leash dog lounge.
Chicago's favorite LGBTQ+ video bar hosts a raucous dog meet-up! Sponsored by Tito's Vodka. Heated, covered outdoor rooftop deck, free dog-friendly swag, and plenty of belly rubs.
Santa photo fundraiser for Live Like Roo! Dress your pup in holiday finery and get at least one edited digital photo. Hot toddies and cold brews for the humans!
4th annual holiday extravaganza! Ugly sweater brunch on heated patio (free zeppole!), $38 bottomless mimosas, then a pet costume parade at 2pm with prizes for Best Dressed Pup!
7th annual Holidawgs event! $50 ticket includes open bar, light snacks, and holiday craft market. Add $20 for professional Santa photos by Jay Dog Photography.
One more festive fling! Pups of all sizes welcome. Pup-safe holiday "mocktails," small bites, selfie station, and 10% off during the event. Just bring a donated item for local shelters.
Smushy Moments photographer sets up shop! Mini sessions include ~5 edited digital photos. Ugly sweaters and matching PJ sets encouraged! Open to non-members for the day.
Late December Celebrations
FREE holiday cheer on your lunch break! Complimentary pet photos with Santa, free hot cocoa for humans, and tasty treats for furry visitors. Warm and welcoming atmosphere.
Even Chicago's oldest pubs go to the dogs for Christmas! Cozy up by the fireplace for a free Polaroid and digital photo with Santa. Complimentary dog treats and drink specials!
This legendary dog-friendly Irish pub hosts annual pet photos with Santa. Free complimentary photo, possible "puppuccinos," $5 holiday pints, and warm mulled wine. Santa hats encouraged!
Massive patio turns into winter playground! Santa photos by vintage camper (included), spiked hot cocoa, free puppuccinos, giveaways, and off-leash play area with fire pits.
Last-minute shopping with your pup! After regular hours, Santa welcomes pets for photos. Doggy bandanas and treats while you wait. Great Danes in reindeer ears welcome!
Ongoing Holiday Highlights
🎅 Santa's Workshop at Gallagher Way
Visit Winterland at Gallagher Way! Dogs welcome to meet Santa on Sundays only (Dec 7, 14, 21) from 11am–5pm. Magical setting by Wrigley Field with twinkling evergreens and Santa's sleigh.
Visit Website →🍻 Doggy Days Saturdays at SoFo Tap
Every Saturday 12–3pm at this Andersonville dog-friendly bar. Free dog treats, half-priced drinks, heated rooftop deck. Watch for "Holiday Edition" with Santa-themed props!
Visit Website →🐕 Yappy Hour at Home Away From Home
Every Friday at 5pm in Wrigleyville! Weekly social hour with doggie menu (mini meatballs, sweet potato fries, puppuccinos). BYOB for humans. Perfect end-of-week wind-down!
Visit Website →🚂 CTA Holiday Train & Bus
Catch Chicago's most festive public transit! Small dogs in carriers can ride the sparkling Holiday Train. Even from the platform, it's a great socialization outing with amazing photo ops!
Check Schedule →Tips for a Paw-sitive Experience
Check Requirements
Many events require reservations or advance tickets. Always check event pages before heading out!
Bundle Up
It's Chicago in December! Bring a coat for your pup and dress warmly yourself for outdoor events.
Bring Treats
Have your pup's favorite treats handy for photo ops — squeaky toys help grab those perky ears!
Know Your Dog
Some events get crowded and loud. Bring only social, crowd-comfortable dogs to busy venues.
Ready to Hit the Town with Your Pup?
Each of these events brings special joy to the holiday season. From wagging tails at brunch to canine costumes under twinkling lights, Chicago's December calendar is overflowing with howli-day cheer!
Grab your leash, don your ugliest sweater, and make unforgettable memories — there's no better way to end the year on a pawsitive note! 🐾
Want to make sure your dog is ready for these social outings? We can help you build the connection, confidence, and calm behavior needed to enjoy any environment together.
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