Pupapalooza: Dog-Friendly Fun in Chicago This Weekend

This weekend is Lollapalooza, so you know what that means. Traffic and crowds are gonna be RUFF. If you’re skipping the festival in lieu of grabbing your pup to hang out with your tongues out, we’ve dug up the best dog-friendly events this weekend in Chicago. 

1. Chinatown Summer Fair

Chinatown, Chicago
Saturday, July 30, 12–10 p.m.; Sunday, July 31, 10 a.m.–7 p.m.

If you’re looking for a dog-friendly festival with great music, delicious food, and Grammable opportunities, point your nose south and head to the Chinatown Summer Fair. This two-day event starts with a lion dance procession and only gets more fun from there. Leashed, well-behaved dogs are welcome at the festival, though organizers warn not to take them inside restaurants. 

2. Jeff Fest Arts & Music Festival

Jefferson Park, Chicago
Friday, July 29, 5–10 p.m.; Saturday & Sunday, July 30–31, 2–10 p.m., $7 at gate

Get ready to howl along at Jeff Fest. This (leashed) dog-friendly music festival spans three days and is the perfect chill vibe for when you’re looking for outdoor concert vibes without the Lolla price tag. Grab a spot on the lawn with a picnic blanket a little further back for sensitive ears and enjoy the show!

3. Morton Arboretum Dog Day

Morton Arboretum, Lisle
Sunday, July 31, 9 a.m.–sunset; tickets required

This is one of the most exclusive tickets in town—and we’re not talking about a sold-out Lolla aftershow. This Sunday, Morton Arboretum is hosting one of its Dog Admission Days, and you won’t wanna miss it. Reserve tickets ahead of time and drive out to DuPage county for a day of fun in the sun. Princess will be pulling on her leash to explore all 16 miles of trails, sights, and sniffs.

4. Fetch a Beer

If fighting crowds and loud noises have you and your floof cowering in the corner, avoid downtown entirely by heading to Balmoral for a DIY beer crawl. This quiet neighborhood is just what the dogtor ordered. Start on Half Acre’s expansive patio before taking a leisurely walk over to Spiteful Brewing where man and man’s best friend are allowed inside to enjoy some A/C. If it’s not too hot, you can continue the crawl down to Empirical for a final sip at another dog-friendly brewery. 

5. Dog Days of Summer

Pilot Project Brewing, Chicago
Tuesdays in August, 11 a.m.–10 p.m. 

Pilot Project Brewing, a beer incubator in Logan Square, is celebrating the dog days of summer all day, every Tuesday. Grab a reservation on Tock and scoop a spot on the patio. But paws before going—each week is themed for a breed of dog. If your pup falls into that category, you can score 15% off your tab (Pilot Project has beer, coffee, and tasty snacks), though all dogs are welcome. Perhaps you can turn those cash savings into a special new fluffy for your drinking buddy? Just a thought…

No pupper in your life yet? Get a heckin’ dog already! 

If you live in a world without tail-wags—what a tragedy—check out this Chicago adoption event!

Aurora Animal Care & Control

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: Brett Sayles

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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