The 9 Best Dog-Friendly Fall Activities in Chicago

Dog-friendly dive bars, Bowser-loving beaches, and so much more.

Throughout the less-than-pleasant past year and a half, one thing has kept me steady: my dog, Oli. The love, the loyalty, the cuddles––we truly don’t deserve dogs, and, honestly, they probably agree. Another thing every dog could agree on? When the pack sticks together, everyone has more fun.

The temps may be on the decline these days, but fall is still a great time to treat your doggo to some outdoor activities before… well, you know, it’s Chicago. From sipping beers on a patio to heading out on a boat tour, there are plenty of ways to ditch the same tree-sniffin’ routine you’ve been clinging to since well before quarantine. Here are the best dog-friendly fall activities around Chicago, all fully endorsed by my tail-wagging, fresh air-loving buddy.

James Andrews1/Shutterstock

Get a little sandy while you still can

Unleash your pup and let them expel some pent up energy during these final days of lake season. Montrose Dog Beach on the northwest corner of Montrose’s, for lack of a better team, Human Beach, is a massive lakefront stretch offering that sweet taste of freedom every city dog craves. A true spectacle, this doggy oasis is overflowing with every breed imaginable, all harmoniously playing, digging, and splashing their hearts out. They even have pay-as-you-go dog showers at the exit so you can bring home an even cleaner pup than you arrived with. Belmont Harbor Beach is another option, but it’s much smaller in size, so it may not be ideal if your dog really likes to run. Perched just north of Belmont Harbor, this waterfront playpen serves as a quality end to a short walk along the lakefront trail. Both beaches are fenced but not impenetrable, so remember to be sure to keep an eye on your little pal at all times.

Mercury, Chicago's Skyline Cruiseline
Mercury, Chicago's Skyline Cruiseline

Relax on a boat cruise or kayak the river with your furry friend

Leash up your pup and hop aboard the Mercury Canine Cruise to float along Chicago’s scenic waters while learning a bit about the city’s architecture and soaking up the epic skyline views. Walk around the boat’s deck and meet some other cultured dog friends, or sit back comfortably with your bestie by your side. And you won’t want to miss dressing up for their Halloween-themed trip on October 1 and 2, complete with their first-ever doggie costume contest. A grand prize will be given to the champion canine, but rest assured everybody will get plenty of pumpkin treats.

If you're looking for a one-on-one experience, pack a life jacket for your Fido and head out on a fall river or lake drift with Kayak Chicago Paddle, which provides kayaks large enough for the whole pack. Open through mid-October (weather permitting), the company operates two weekend-only lake launch sites and one daily river launch site, so opportunities to experience this unique bonding adventure abound.

Green City Market
Green City Market

Enjoy a leashed stroll through a local farmers market

Perusing local farm stands with your trusty companion is a perfect fall activity, with weekly markets sprinkled around the city running through the end of October. A favorite is Logan Square Farmers Market, going down on Sundays from 9 am to 3 pm on Logan Boulevard between Milwaukee Avenue and Whipple Street. In addition to all the good food and vibes, this option sports ample green space so you and Spot can stretch out on the grass and enjoy your findings. Another gem is long-standing Green City Market May in Lincoln Park, open Saturdays from 8 am to 1 pm on North Stockton Drive. Here, you can stock up on fresh-picked produce, walk along the nearby lakefront, and partake in ready-made cuisine from prominent chefs.

Andersonville Farmers Market
Andersonville Farmers Market

Other dog-centric outdoor markets include Andersonville Farmers Market (Wednesdays from 2 pm to 7 pm), Wicker Park Farmers Market (Sundays from 8 am to 2 pm), and Wood Street Urban Farm Stand (Fridays from 3 pm to 7 pm). The harvest season’s bounty awaits, along with other fun attractions like live music and restaurant pop-ups. Your dog might take also advantage of the abundance of food scraps left behind in the grass—don't worry, it’s mostly apple slices and cheese samples. A win for you, a win for good old Scout.

Doggy Paddle Aquatic Center for Dogs
Doggy Paddle Aquatic Center for Dogs

Dive into an indoor doggie pool

Just because it’s getting a little chilly, doesn’t mean your dog has to wait until next summer to splash around with his buddies. Doggy Paddle is a Wicker Park aquatic center and boarding facility providing an impact-free way for your dog to get out their energy while making a few friends along the way. If water confidence doesn’t come naturally to your pup, staff members are on hand to gently introduce your dog to the pool—in no time they’ll be ready to tackle the big kids at the lake. Regardless, this place does an excellent job creating a safe, fun, and all-around friendly atmosphere, and, as we all know, a wet dog is a happy dog (bathtime excepted).

Candice C. Cusic Photography
Candice C. Cusic Photography

Pose for a professional pet portrait

It’s time to start treating your dog like the top model he is, and what better way to put your money where your snout is than to start building up their elite portfolio. It’s never too early or too late to capture some outrageously cute portraits for your holiday cards, customizable Etsy finds, or simply to post on your pup’s personal ‘Gram (because you know you have one). Both Van & Bella’s in East Village, and Candice C. Cusic in West Town will produce mesmerizing photos of your one and only, with their artful eye and impeccable timing. Honestly, anyone who’s ever tried to get a rambunctious dog to sit still for a picture knows that nailing it is truly an art form—best to leave it to the professionals.

Rovsky/Shutterstock

Give your pooch a little taste of luxury—they deserve it

In need of a little puppy pampering? There are endless doggie spas across the city to choose from. Whether they need their nails trimmed, their fur conditioned, or their teeth deep-cleaned, these specialists know how to make Mr. Boogers feel just the right amount of spoiled. Standouts include Grooms by Glady over in Rogers Park, which will treat your dog like family while their talented technicians take their time giving your puppers a new furr-do. Urban Pooch in Ravenswood will not only pretty-up your dog, they also have expert trainers and nutrition counselors on staff, because, as we all know, true beauty comes from within.

Urban Pooch Canine Life Center
Urban Pooch Canine Life Center

If you’re looking to treat your furry pal to a weekend getaway, Pet Care Plus hosts an open pool party on Saturdays from 10 am to 12 pm, or you can reserve private parties for birthdays, gotcha days, or breed meetups. Furtastik in West Lakeview offers a holistic approach to their grooming practices for more sensitive canines, while Temple of the Dog & Meow Lounge in Palmer Square (arguably the best business name), will personalize any care your dog needs at their full-service beauty and wellness spa.

Half Acre Beer Company
Half Acre Beer Company

Crush beers with Benji at your side

Knocking back a crisp pint with your furry pal is a fall no-brainer here in Chicago, a city rife with dog-friendly patio bars, taverns, and everything in between. Sportsman’s Club in Ukrainian Village is a local go-to, boasting a massive back patio and plenty of elegant cocktails, to boot. If you're wanting to spread out a bit with your four-legged friend, Half Acre recently unveiled a stellar dog-loving patio up in Rogers Park, peddling great bar bites alongside loads of delicious seasonal brews.

Over in West Town, Midwest Coast Brewing Co sports a roomy dog-friendly taproom and breezy fenced-in patio, so you can move between the two at your leisure while simultaneously pounding $5 crowler specials every Sunday. Dovetail in North Center welcomes dogs to their beer garden and patio, where they serve up small batch Euro-style brews inspired by their love for traditional brewing methods, while the personable folks behind Lo Rez in Pilsen pair puppy love with tasty house-brewed beers at their charming Fido-friendly patio. Elsewhere, Bucktown Pub, open since 1932, is your quintessential no-frills neighborhood pub and invites dogs to take advantage of their laid-back indoor-outdoor expanse and everyone’s favorite Humboldt Park dive, Archie’s Rockwell Tavern, keeps a big barrel of cheese puffs behind the pine, ready to please both you and your well-behaved pup whenever hunger strikes.

Parson's Chicken & Fish - Logan Square
Parson's Chicken & Fish - Logan Square

Dine out at a dog friendly patio

Chicago is brimming with outdoor dining options, and many are well suited for a canine dinner date. Multi-location standby Parson’s chicken & Fish is famously pet-approved, serving up delicious fried chicken and fish as well as game-changing Frozen Negronis to dog-parents gathered beneath their iconic red-and-white-striped patio umbrellas. If you're craving classic pub grub like burgers or wings, neighborhood hangout Moonlighter over in Palmer Square has loads of picnic tables for you and your dog, making for an ideal spot to sit back and indulge (and maybe throw the lil’ guy a fry or two).

Saint Lou’s Assembly
Saint Lou’s Assembly

Big Star’s sprawling Wicker Park original delivers big time when it comes to tacos and cocktails, and the atmosphere is just right for doggie tagalong. Known for its gigantic sidewalk patio, the venerable cantina is conveniently located across the street from Wicker Park, so you’ve got no excuse when it comes to a romp on the grass post-taco fest. Before you leave, don't forget to tag #DogsofBigStar when you inevitably post an Instagram pic of your cutie eyeing a big pitcher of margaritas.

The Royal Grocer in Bucktown has a covert dog-friendly patio out back, primed and ready for you and FiFi to lap up delicious farm-to table dishes alongside seasonal cocktails and rotating wine and beer list. In the West Loop, Saint Lou’s Assembly takes staples like grilled cheese sandwiches and classes them up with apple butter and sun dried tomatoes. All their tasty creations can be enjoyed on a beautiful side patio tucked away from the city street—a cozy place for a night out with you and your four-legged brethren. Last but not least, Asian-fusion hotspot Mott Street invites doggies of all shapes and sizes to their fenced-in outdoor area for a full night of Char Siu Pork Belly-fueled revelry.

West Loop 569 Bark Park
West Loop 569 Bark Park

Lose a tennis ball (or five) at the dog park

Sure, everyone has their favorite place to let their dog run free—whether or not it’s officially sanctioned—but sometimes it’s nice to venture into a nice fenced-in patch of land and extend your canine’s social network. Adjacent to Millennium Park in the heart of the Loop, Lakeshore East Dog Park is littered with gardens, benches, and a whole lot of downtown dogs ready to sniff and mingle. And hey, the skyline backdrop makes for a pretty nice human destination, too. Take a brisk fall jog down the 606 in Wicker Park and you’ll stumble upon a hopping dog run at the east end of the trail in Walsh (John) Park. The park takes up just over two-square-acres, and aside from the doggie zone, holds an athletic field, basketball hoops, and a playground.

Wrigleyville is home to Chicago’s first ever dog-friendly park, the adorably named Wiggly Field. This no-frills urban escape has plenty of space for playtime, and is secured by double gates for good measure. 569 Bark Park in the West Loop is a pristine option, strewn with benches and sunny clearings for your dog to let loose. Logan Square Dog Park, nestled in buzzy Logan Square, is an expansive one, with separate sections for small dogs and bigger buddies—ideal for a size-appropriate playdate. And if you have a little extra time, trek out to The Morton Arboretum, where November 7’s special fall doggie day lets you traverse all or part of the institution’s gorgeous 16 miles of natural wonderland for just $5 a pup (get it?). It’s a great opportunity to get out of the city for a few hours—not to mention a great way to peep changing leaves.

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Elanor Bock is a contributor for Thrillist.