Your Dog-Friendly Chicago Weekend: October 27-31, 2022

Howloween is just days away and the spooky season is in full swing. A smattering of dog-friendly events across the city ensure you and your pal will have plenty to enjoy. Get those costumes ready and read on to start planning for the ulti-mutt dog-friendly Chicago holiday weekend. 

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1. Doggie Halloween Party

Park and Field, Chicago 
Thursday, October 27, 6-9 p.m.; Registration required

Park and Field Après, Palos Hills
Sunday, October 30, 4 p.m.; Registration required

When Park and Field debuted in Logan Square in 2016, the vintage-themed sports bar—complete with a massive patio and dericious doggie menu—raised the bar on what it meant to dine out with your dog. Six years later, it’s hosting a Halloween Party in Chicago and Palos Hills that includes a costume contest, drink specials for you, snackies like their “pooch patty” for floof, and giveaways—all benefiting charity. 

2. 35th Annual Streeterville Doggy (and Kitty) Halloween Party

Museum of Contemporary Art’s Kern Terrace Garden, Chicago 
Saturday, October 29, 9-10:30 a.m.; Registration recommended

For more than three decades, the Streeterville Doggy (And Kitty) Halloween Costume Party and Parade have featured some of the city’s best-dressed pets. This year, the free event returns for its 35th year at the Museum of Contemporary Art’s paws-itively beautiful Kern Terrace Garden. Alderman Brian Hopkins (2nd Ward) and publicist Maureen Schulman will judge the doggy parade’s best-dressed doggos at 9:30 a.m. For the felines staying at home, participation is open for the Virtual Cat Costume Contest on Facebook. Organizers ask that all attendees bring a dog toy so every good boi and girl can head home with a prize.

3. Wag-o-ween Dog-friendly Market

Bosly’s Backyard, Chicago
Saturday, October 29, 12-4 p.m.; Tickets required

This pupular indoor play space in Ravenswood introduces Wag-o-ween, one part trick-or-treat celebration and one-part makers market. Twenty vendors will be on hand, offering everything from screen printed apparel to all-natural gourmet dog treats and espresso drinks served out of a 1970s mail truck. The $10 per-person ticket price includes a Halloween themed photo booth, tote bag, puppuccinos, mini massages, brush outs, pup cups, costume contest offering winners a free Bosly’s play session, and mutts more. With proceeds pawsitively benefiting Safe Humane Chicago, what’s not to ruv? 

4. 569 Bark Park Howl-O-Ween Social

569 BarkPark (inside Skinner Park), Chicago
Saturday, October 29, 1–3 p.m.; Tickets required

Ghosts, goblins, ghouls… oh my! Dress up in your Howloween best (dog/human matching costumes anyone?) and pounce over to this West Loop dog park where raffle prizes and a photo shoot will surely get you in the spooky spirit while simultaneously supporting a great cause. Since the park relies solely on donor support, ticket donations (starting at $10) will go toward the maintenance and improvement of the park, ensuring your best fren and their pals continue to enjoy all of its wonderful amenities.

5. Eckhart Park Howl-o-ween Fest

Eckhart (Bernard) Park, Chicago
Saturday, October 29, 9:30 a.m. to 12:30 p.m. Registration required

This West Town park will be pupulated with pumpkins, a photo booth, and dog and cat treats during the Eckhart Park Advisory Council’s inaugural Howl-o-ween Fest. Tickets start at $15 and include one pumpkin, one gift basket raffle ticket entry, and unlimited Instagram photo ops. Afterwards, head down the street to check out the neighborhood’s vast array of pet-friendly businesses, like quaint gift store Dovetail, plant purveyors The Plantier and Plant Salon, and wine and spirits shop The Noble Grape. Once you and pupper have worked up an appetite, chow down on some noms at the nearby Roots Handmade Pizza’s dog-friendly patio.

6. Arts in the Dark Halloween Parade

Eckhart (Bernard) Park, Chicago
Saturday, October 29, 6-8 p.m.

Serving as the spirited grand finale of the city’s Halloweek Program, the 8th annual Arts in the Dark Halloween Parade takes over historic State Street southward from Lake to Van Buren streets with distinctive floats, spectacular puppets, and creative performances—all completely free! The celebration—a public-private partnership between LUMA8, the City of Chicago and the Chicago Loop Alliance—will include appearances by the Joffrey Ballet, Lookingglass Theatre Company, and more. Head downtown early or stick around after the parade to grab a bite at the many dog-friendly restaurant patios

7. Haunted Halsted Halloween Parade & Costume Contest

Intersection of N. Halsted St. & W. Belmont Ave., Chicago
Monday, October 31, 6:30-10 p.m. Registration required for costume contest

Drag queens, kids, parents, and pets march in unison at this longtime north side parade, which features some of the most creative costumes in the city. Dress to the (ca)nines and head out to historic Northalsted with your furry crew early, because this popular event gets downright busy. The parade officially kicks off at 7:30 p.m. and features $4,000 in prizes across five categories, including scary, creative, and couples. Stick around for the award show that commences at Halsted and Roscoe at 8:30 p.m.

Don’t have a dog already? Get a heckin’ dog!

Spending Halloween without a hound is just nonsense. Explore these local adoption events happening this weekend to meet your new best furrend.

West Suburban Humane Society 

  • Woof! October is “Adopt a Shelter Dog Month,” and the West Suburban Humane Society has partnered with Gerald Subaru to provide discounts on all dog adoptions. Meet adoptable pets from the humane society beginning at 11 a.m. through the end of the month in Downers Grove

Sniff out more events on our calendar and submit your own events here. And don’t furget to tag us @SidewalkDog in pics of your tail-waggin’ weekend!

Featured photo: Paige Cody

Sidewalk Dog’s mission is to help dog parents spend more time with their puppers by discovering and sharing activities they can do and places they can go—together! Sniff out our award-winning newsletter and Instagram, and join our Dog-Friendly Chicago Facebook Group.

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