Food Trucks and Rainbow Tails: Your Weekend To-Dos

Make every day a dog day of summer! We’ve sniffed out the best dog-friendly events in Chicago this weekend so grab your leash, the poop bags, your bff, and get to pawty-ing. 

P.S. Don’t miss a single weekly event again! Pupscribe to our newsletter here.
P.P.S. Our Patio Leash™ is grrreat for outings and adventures of all shapes and smells.

1. Yappy Hour Pride Week Edition

The Northman, Chicago
Wednesday, June 22, 5–8 p.m.

Is there anything cuter than a pupper parade? Doubtful. This Wednesday, your furbulous fren can join the “Fabulous Puppy Parade” hosted by Chicago’s own Miss Foozie. Pup’s gonna need to work it cuz attendees can vote for the 1st, 2nd, and 3rd most fabulous floofs in the parade. And while you’re taking in all the adorableness, sip on Seattle Cider Company and feel great knowing that 25% of sales will go to our pals at PAWS Chicago.

2. Chicago Food Truck Fest

South Loop, Chicago
Saturday and Sunday, June 25–26, 11 a.m.–7 p.m.; tickets required

Chicago’s food scene always gets our tails waggin’! South Loop’s Food Truck Fest brings the best gourmet meals on wheels offerings around. Admission is free but bring your wallet for some tasty treats. This year’s festival has a special dog park area where your furry fren must stay, but it’s the pawfect spot to nosh and play while staying off the hot pavement. 

3. Sit Social Grand Opening Party

Sit Social, Chicago
Saturday, June 25, 12–6 p.m.; tickets required 

Sit Social is having a pawty and you’re invited! This woman-owned business is celebrating 10 years and a new store opening. Check out the new digs while you meet and mingle with other pups and pawrents. You may wanna slide a pamphlet about their Canine Social Club into your bag to look into later—somepuppy would like to go to a couple yappy hours. 

4. Doggy Days 

The Sofo Tap, Chicago
Saturday, June 25, 12–3 p.m.

Every Saturday at The Sofo Tap is time for Doggy Days! Leash pup and head over for free dog treats, half-priced drafts, and their “Cheap Drinks Everyday” specials. Rover thinks she needs a ROYGBIV tail to really strut her stuff for this one. 

BONUS: Speaking of Pride, for the most muttropolitan of pups who can brave the crowds, this Sunday, June 26, marks Chicago’s 51st Pride Parade. Animals are welcome, but it’s best to stake out a spot bright and early (parade starts at 12 p.m.) or maybe grab a bite on a patio (like nearby Wilde Bar & Restaurant) where you can watch all the excitement pass by.  

5. Dog Days at Cantigny

Cantigny Park, Wheaton
Saturday, June 25, 10 a.m.–4 p.m.; $10 parking fee required

For one day only, doggos and those who ruv them (all of us) can stroll the gorgeous grounds of Cantigny Park. There’ll be adoptable pups on-site (more on that below) as well as tons of fun activities, like a peanut butter licking contest and, well, we’re gonna guess we had your pooch at “peanut butter.”

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

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


  • Our best buds at Animal Rescue Foundation will be at Cantigny Park’s Dog Days this Saturday, June 25 from 10 a.m.–2 p.m. Before going, be sure to fill out an adoption application so that pesky paperwork can’t distract you from what you’re really gonna want to be doing—petting pups, duh. 

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: Vlad Tchompalov

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:

Your email address will not be published. Required fields are marked *

The internet’s most dog-friendly website. Sidewalk Dog is your go-to resource for all things dog. Trusted by more than 250,000 dog people around the world.

Join the Pack