Three Days of Doggo: Your Chicago Weekend   

Pretty girl in hat hugging little cute dog joyfullylooking in camera spending time on picnic in park with red bicycle on background

Did someone say three-day weekend? You’ve got an extra day to play, and pup’s been beggin’ for more time with you. Plan your howliday weekend with our dog-friendly Chicago to-do list. 

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P.P.S. Keep doggo close with our exclusive Patio Leash™—it’s the pawfect length for when you’re out and about!

1. Canine Cruise

Mercury Cruiseline on the Riverwalk, Chicago
Saturday, September 3 and Sunday, September 4, 10:15 a.m.; tickets required

We can’t think of a better way to spend the unofficial end of summer than cruising Chicago’s waterways! Sit back, relax, and soak in the city as you and pupper enjoy a lively narration of Chicago’s rich history and architectural marvels with dog-friendly highlights. Mercury’s dog cruise offers plenty of safe outdoor seating, water bowls for thirsty pups, bar and snack service for humans, and an exclusive newspaper-lined restroom for your pet.

2. Sunflower Stroll

M & D Farm, Homer Glen
Friday Sept. 2, 9 a.m.–6 p.m.; Saturday, Sept. 3 and Sunday, Sept. 4, 9 a.m.–5 p.m.

M & D Farms And Garden Center in Homer Glen is a family-owned and operated farm and greenhouse, and home to an absolutely corgi-ous dog-friendly sunflower field. The sunflower patch opened August 27 and will run for only 2 weeks, so get your paws there this weekend for this limited time pupportunity! Check their Facebook for more info, and don’t furget to clean up after your pet!

3. Saturday Pup Crawl

The SoFo Tap and Sidetrack, Chicago
Saturday, September 3, 12–3 p.m. at SoFo and 1–5 p.m. at Sidetrack

Wanna create your own pup crawl that’ll take you and your fren to not one but TWO furbulous LGBTQIA+ bars? Start at The SoFo Tap where every Saturday is Doggy Days and they’ll be serving up free dog treats, half-priced drafts, and their “Cheap Drinks Everyday” specials. Keep the pawty going at Sidetrack for their monthly Dog Day where the drinks and treats will be flowing, and pup may even score some pawesome swag from Tito’s Handmade Vodka.

4. Sundays on State

The Loop, Chicago
Sunday, September 4, 11 a.m.–6 p.m.

Bark your calendars because this year’s final Sundays on State is this weekend, and pupper does not want to miss it! Point your paws to Chicago’s most iconic street to experience this free block party where you’ll find art, culture, recreation, food, drinks, shopping, and more. Feeling lucky? If you pre-register to attend (totally optional), you’ll be entered for a chance to win a $1,000 Loop Staycation package. 

5. Best In Show

Buffalo Grove & Long Grove   
Saturday, September 3, see times below

Point your paws northwest for two amatuer dog shows happening this weekend. Start out in Buffalo Grove for their annual Dog Show at 10:45 a.m. where any dog is welcome to compete in events like best-groomed, celebrity look-alike, best couple (dog and owner), best trick, waggiest tail and best costume. Continue the fun a few miles away in Long Grove for their annual Irish Days festival from 10:30 a.m.–7:30 p.m. on Saturday. Enjoy Irish music, merchants, cuisine, and the Irish Dog Competition where pups dressed in costumes compete. A panel of child judges will crown an Irish Doggie King, Queen, Prince, and Princess. Enter your fur babe the day-of at the competition area located by the Long Grove Information Center.

6. Paint Your Pet

Cork & Bean, Oak Lawn
Sunday, September 4, 3–6 p.m.; tickets required

We know floof wants to spend all weekend with you, but she’ll forgive you for leaving when you bring home her very own portrait! Paint your pup at Cork & Bean where they provide all the supplies you need to make a 16 x 20 inch canvas masterpiece. Upon registration you’ll email a photo of your pet, and then after a few sips of wine on Sunday you’ll be painting like Picasso!

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

Sniff out these local adoption events happening this weekend to meet your new slobbery soulpup.

The Anti-Cruelty Society

  • The Anti-Cruelty Society’s River North and South Loop adoption centers are closed on Labor Day, so pick out a furry fren this weekend and have all day Monday to get doggo settled in. Preview the available animals online and just try not to ooh and ahh at all the cuteness! Before you go, get your paws on these adoption details.

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!

Photo by Ashley Williams

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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