Your Dog-Friendly Chicago Weekend: October 20-23, 2022

Howloween is right around the corner and there’s no shortage of activities for you and your best furrend to spend some quality time together. Read on to learn how to get a jump-start on your dog-friendly Chicago weekend. 

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1. Pups on the Patio Costume Contest

Lucky Dorr Patio & Tap, Chicago (located at Gallagher Way) 
Thursday, October 20, 4–10 p.m. 

Hoomans in the loop know Howloween doesn’t have to be limited to a single day! This free, annual event just steps from historic Wrigley Field is back bigger and better, complete with an expanded pup-friendly beer garden, photo booth, and specialty dog vendors and organizations. The hour-long costume contest will be live streamed on the Gallagher Way video board, ensuring it’s the place for pupper to see and be seen. 

2. Spooky Film Fest

Solidarity Triangle, Chicago (formerly known as Woodard Plaza)
Thursday, October 20, 6 p.m. 

Bundle up and sniff out the best spot at this free outdoor showing of Monster House, the second of three family-friendly spook-tacular movies presented by the Northwest Arts Connection this season. The organization—working to enrich Northwest Side neighborhoods like Austin, Logan Square and Edison Park—will also provide well-mannered hoomans free snacks and warm drinks from neighborhood businesses. 

3. Lakeview Halloween Pup Crawl 2022

3311 N. Halsted Street, Chicago (corner of N. Halsted Street & W. Aldine Ave.) 
Saturday, October 22, 10 a.m.–2 p.m.; Tickets required 

You and your best fren will surely get your daily steps in at this annual trick-or-treat celebration in the historic Northalsted neighborhood. Register online or in-person the day of for $10. Each entry includes tasty treatos, goodie bag, prize raffle, and access to a costume photo booth. Then, hit the streets to shop at various dog-friendly businesses spanning Belmont Ave. to Cornelia Ave. Once you’ve worked up an appetite, head to Lark Bar’s pup-approved patio for some brunch noms from 11 a.m. to 3 p.m. Emcee Miss Foozie will host a lively raffle presentation at 2 p.m. 

4. Treatos for Tricks Grand Opening Bash

Squeaky Bea’s, Chicago
Saturday, October 22, 11 a.m.–5 p.m.

Home to one of the city’s most-popular pup-friendly farmers markets and a plethora of floof-friendly businesses, Logan Square has rightfully earned its reputation as one of Chicago’s most dog-friendly neighborhoods. So it’s no surprise that Squeaky Bea’s, a newly-opened pet supply store and boutique, is going all out for its free-to-attend grand opening celebration. This one’s packed with goodie bags, a costume contest, boozy sips from local, women-owned Eris Brewery & Cider House, pizza from dog-friendly Pizza Lobo, flash sales, and a complimentary photo of pups in their aww-dorable costumes.

5. Arts in the Dark UPSIDE DOWN Halloween Parade

Washington (George) Park, Chicago 
Saturday, October 22, 12-3 p.m. 

As the official opening of Chicago’s Halloweek Program, this totally free daytime celebration “turns the traditional parade upside down” because families in costumes will be the ones walking the parade. Well-mannered, leashed floofs are welcome to watch the dancers, acrobats, puppetry and sports mascots. That’ll ensure some serious stimulation! Bring the whole pack cuz kiddos will love the complimentary goodie bags from Chicago’s own Blommer Chocolate Company. 

6. Halloween Pet Portrait Pop-up by Fetch Portraits

Mau’s House, 901 S. Plymouth Ct., Chicago 
Saturday, October 22, 2-5 p.m. 

Your photogenic fur babe doesn’t need a reason to say “treats” and smile, but here’s some additional motivation. Fetch Portraits is hosting a Halloween Pet Portraits Pop-Up where you’ll walk away with a free 5×7” print and feel doggone good about it as a portion of every $40 session benefits Chicago-based nonprofit Canine Therapy Corps. Hoping to bring the whole fam? No problem. Both events are family-friendly and welcome other household pets, including cats and bunnies, too.

7. Halloween Town at Wicker

Wicker Park, Chicago 
Saturday, October 22, 10 a.m.-1:00 p.m. 

After the neighborhood’s long-time Halloween festival, Boo-Palooza, was canceled earlier this year, neighbors were left wondering if a replacement might materialize. Good news: While not specifically oriented to pups, organizers say the new Halloween Town at Wicker happily welcomes leashed puppers to the namesake park. Complete with live music, candy, spooky games, face paintings, pumpkin giveaways, costume contest and parade, and holiday-themed arts and crafts activities, the free event geared toward kids 12 and younger is a great fit for the whole family. 

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

Going into Halloween with no dog to dress up is just plain scary. Check out these local adoption events happening this weekend to meet your new bestie.

PAWS Chicago

  • PAWS Chicago has so many lovable companions lookin’ for homes right now. Meet adoptable pets from PAWS this Sunday, October 23 from 12–4 p.m. in Roscoe Village.

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: Josh Hild

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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