Your Dog-Friendly Chicago Weekend: December 8-11, 2022

Sports woman in a red sweater. Woman in a summer park. Lady with a dog

Make it a December to remember with doggo! From holiday drive-in movies to cheerful markets and festive fundraisers, there’s no shortage of dog-friendly events across Chicagoland this weekend. So grab the leash, throw on a warm coat and hat, and head out of the house with pup! 

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1. ChiTown Drive-In Movies

2343 S. Throop St., Chicago
Thursday, December 8–Sunday, December 11, showtimes vary; Tickets required

Drive-in theaters of the past have made a resurgence nationally and here in Chicago, they’ve returned in a BIG way. Bundle up with your best buddy and drive to Pilsen to catch classic holiday flicks, including “Elf” on Thursday and “How the Grinch Stole Christmas” on Sunday. Gates open about one hour before showtime, depending on the movie. Make it a “dinner and a movie” date night with doggo cuz the on-site restaurant delivers tacos, wings, burgers, pizza, popcorn and drinks right to your vehicle. 

2. Winterglow Holiday Market & Beer Garden

The Salt Shed, Chicago
Updated hours: Friday canceled. Saturday & Sunday, December 12–8 p.m. Tickets required

Winterglow, the eclectic winter market and beer garden, returns for one final week at the newly-opened Salt Shed complex on the North Branch of the Chicago River. Leash up your furry fren and roam this sprawling space complete with artisan vendors selling gifts, jewelry, vintage clothes, home goods, and more. After working up an appetite, head to the cold-weather beer garden and warm up with hot cocktails and treats like s’mores around riverfront fire pits. Food trucks, including Chicago fan favorite Stan’s Donuts, are on site, as are numerous outdoor lawn games like bocce ball and corn hole. Live ice sculpting will also take place on Sunday. Admission is $6 per person, but kiddos 12 and under are free. 

3. Santa Paws at PupStars Pet Care

PupStars Pet Care, Chicago
Saturday, December 10, 12–4 p.m.

Snap a photo with Saint Nick at this West Town dog groomer, retail shop, and outdoor private dog park that’ll make all your furrends jealous. Snag some derricious T-R-E-A-T-S before taking a tour of the facility. A suggested donation of $10 will benefit Paw Salvation, a nonprofit organization dedicated to helping care for Chicago’s homeless population who own pets. 

4. Holiday Open House

Anything Is Pawzible, Chicago 
Saturday, December 10, 1–3 p.m.

Mini massages? Check. Baked goods for dogs? Yup! Hooman holiday drinks? You bet. Head to Anything Is Pawzible’s new Avondale location with pupper, where over a dozen local vendors will be on-hand for their holiday open house. Don’t have a pal of your own? Dogs from local rescue organizations will also be available to meet and adopt. End the day at the many dog-friendly shops and restaurants in Avondale and neighboring Logan Square, including Pizza Lobo, Fleur, Sleeping Village, and Festive Collective.  

5. One Tail at a Time’s Winter Wonderland

Park & Field, Chicago
Sunday, December 11, noon–3 p.m.; Tickets required

Help end pet homelessness and celebrate holiday hoopla at this outdoor winter wonderland organized by two of the city’s most well-known doggo-oriented organizations. Sip warm beverages from a commemorative mug and snuggle up with your furbabe on Park & Field’s expansive heated patio in Logan Square. Canine tickets are available in a limited quantity—just be sure your pooch is up-to-date on their shots and likes to be around other pups.

6. HOWLiday Wag N’ Shop Market and Fundraiser

Bosly’s Backyard, Chicago
Sunday, December 11, noon–4 p.m.; Tickets required

Complete your howliday shopping at this one-part market and one-part fundraiser for Chicago-based Live Like Roo, which provides assistance to families whose pet faces a cancer diagnosis. A roster of 20 vendors will be selling a wide assortment of goodies for your goodest boi or girl. After you’ve made a serious dent in your list, head to the winter-themed photo booth and snag a drink at the espresso bar before unwinding with mini massages. Ticket admission includes a tote bag and entry into a raffle to win a play session at Bosly’s Backyard and vendor goodies.

7. Mid-week bonus: Shopping and Pet Photos with Santa

Yorktown Center, Lombard
Tuesday, December 13, 11 a.m.–8 p.m.

The slogan for Lombard’s YorkTown Center is #YesToYorkTown and that includes whether Fido is welcome! The newly-revamped hub bills itself as America’s number one dog-friendly shopping center and it’s easy to see why. Many stores are dog-friendly—just look for the paw print graphic in storefront windows. After you pick up a few presents, walk your pal to Santa’s Workshop for photos with Kris Kringle himself. Heads up: The jolly man takes a break to feed his reindeer from 3–4 p.m. 

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

There’s snow one like a rescue dog this holiday season. Make new memories by bringing home a doggo from one of these upcoming local adoption events.

Rover Rescue

  • Join Rover Rescue at Aurora’s PetPeople store on Saturday from noon to 2 p.m. to meet adoptable dogs and learn about fostering options. Available dogs will be posted the day before the event. 

Chicago Pet Rescue

  • This foster-based rescue organization is popping up at the Norridge Petco store on Sunday from 10 a.m.–2 p.m. Meet adoptable doggos (and cats) and learn how you can help animals in need with donated food, toys, and supplies. 

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: Kameron Kincade

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.

More reads you’ll ruv:

  1. Last year, my girl Milky and I spent a weekend in Chicago Grant Park, which is the quintessential dog lover’s paradise. An open, green park that is lush and alive provides us with the space we require. On a hot summer day, you can run, play catch, or simply relax in the shade of a tree. I can’t wait to visit all of the places you’ve suggested.

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