Your Dog-Friendly Chicago Weekend: November 18-21, 2022

Here’s the sitch: You gotta get a head start on your holiday to-do list and woofer’s beggin’ to meet new furry frens. Make the most of both of your weekends by high-tailing it to one of these dog-friendly holiday events in Chicago. (You’ll thank us later).

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1. Winterland at Gallagher Way

Gallagher Way, Chicago
*November 18–January 8, Monday–Thursday from 3–9 p.m., Friday–Saturday from 11 a.m.–10 p.m., and Sunday from 11 a.m.–7 p.m. (*Special hours for Thanksgiving and Christmas)

The team behind Wrigleyville’s massively successful Gallagher Way project are cranking up the “Tis the season” spirit this year with a bigger (and still free) Winterland experience inside and surrounding Wrigley Field. Joining the uber-festive Christkindlmarket and outdoor ice rink (now located inside the ballpark) are rides like “Hot Cocoa Cups” and “Winter Whirl,” a “Wintertube” ice slide, games, and an après-ski-style lodge featuring fire pits, food, and drinks. Woofer will wanna make sure she’s dressed warmly because all activities are dog-friendly, aside from those happening inside the ballpark. Admission is free, but some attractions require tickets for purchase. 

2. Christkindlmarket Chicago

Daley Plaza, Chicago
*November 18–December 24, Sunday–Thursday from 11 a.m.–8 p.m., Friday–Saturday from 11 a.m.–9 p.m. (*Special hours for Thanksgiving and Christmas)

The arrival of the first snowfall signals it’s time to leash (and bundle up) your buddy and head to one of three Christkindlmarkets in the region: Downtown at Daley Plaza, Wriggleyville and Aurora. The German-style outdoor market is a popular place to shop for stocking stuffers like hand-made ornaments. While you sip warm mulled wine and hot chocolate from the special annual collective mugs, your dog will be taking in the dericious smells (and maybe leftover schnitzel). Keep dogs out of the walk-in cabins and tents, unless you want to end up on the naughty list this year. 

3. Magnificent Mile Lights Festival

410 N. Michigan Ave., Chicago
Friday, November 18, 4 p.m. and Saturday, November 19, 11 a.m.–4 p.m.

Many Chicagoans deem this event the official kick-off to the holidays. The show stopping spectacle of lights spans more than 200 trees along Michigan Avenue. Pupper will love the stimulation from the procession of floats, marching bands, soaring helium balloons, and celebrity sightings from Mickey Mouse and Minnie Mouse. Settle in early on Saturday during Lights Festival Lane and check out the full roster of activities. Pose for an awwdorable photo with Santa himself before catching the fireworks display at 6:55 p.m. 

4. Shine Light Show

Northbrook Court Mall, Northbrook (Tickets required
Wintrust Field, Schaumburg (Tickets required)
Friday, November 18–Sunday, January 1, 6–10 p.m.

Sniffing out the best stocking stuffers is hard work for the woofer. Queue up “Christmas is Going to the Dogs” and treat her to one of two cozy drive-thru Christmas light shows. First conceived as a safe, socially-distanced event during the pandemic, Shine Light Show features more than 1 million LED lights synchronized with holiday music. Each location has its own unique festive experience, music playlist, and immersive light displays. Paw tip for families: Print off a few copies of the event’s free activity sheet—the kids’ll stay busy long after you’ve exited the show. 

5. Doggy Days

The SoFo Tap, Chicago
Saturday, November 19, noon–3 p.m.

Short-paw for “South of Foster,” The SoFo Tap is one-part dog-friendly gay bar and one-part Andersonville neighborhood institution. It’s no wonder their recurring Doggy Days events have become the bark of the block. Floof will love the free dog treats and you’ll love the half-priced draft beers and $5 signature margaritas. As Christmas approaches, you’ll want to keep your ears perked for news on an appearance by Saint Nick himself. 

6. Pet Nights with Santa

Oakbrook Center, Oak Brook
Mondays, November 21, 28, and December 5, 4–7 p.m.; Tickets required

Let’s face it: Your pup has been on your tail about getting her “holiday card-ready.” Stop procrastinating and head to Oakbrook Center for Pet Nights with Santa. Each session in the speedy event is just 15 minutes long, providing you plenty of time to make a serious dent in your holiday gift list. With more than 180 stores on site, finding something for everyone is nearly foolproof. If you’re feeling extra festive, drop off a donation for The Humane Society of the United States

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

Ring in the season of giving: Provide a rescue dog a new furever home. Get started by sniffing out one of these local adoption events.

Chicago Wolves Adopt-A-Dog Program

Animal Rescue Foundation (A.R.F.) 

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: Trevor Michael

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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