Chasing Tails in Chicago, Illinois
- Luie Boone
- 3 days ago
- 10 min read
This travel spot is featured in our seventh blog series, Sheps Stay.
No trip to Chicago, Illinois with your dog is complete without a visit to Montrose Dog Beach, the city's only official off-leash beach. Here, your pup can splash in Lake Michigan, run through the sand, and make new furry friends while you take in stunning views of the Chicago skyline. This one-of-a-kind destination combines the excitement of a big city with the freedom of a lakeside adventure, making it one of the most unique dog-friendly experiences in Chicago.
Beyond Montrose Dog Beach, you’ll quickly discover why Chicago is considered one of the most dog-friendly cities in the Midwest. From beautiful parks and scenic walking trails to welcoming patios and plenty of outdoor adventures, Chicago offers countless ways for you and your pup to explore together. Whether you’re visiting for a weekend getaway or an extended vacation, there are plenty of dog-friendly experiences waiting for you throughout the city.
If your pup enjoys long walks, head to the Lakefront Trail, which stretches for nearly 18 miles along Lake Michigan and offers breathtaking scenery, plenty of green space, and countless photo opportunities. Lincoln Park is another must-visit destination, featuring beautiful gardens, tree-lined walking paths, and plenty of room to enjoy a relaxing stroll together. The Chicago Riverwalk is perfect for an afternoon walk, where you’ll find public art, waterfront views, and outdoor seating areas that welcome dogs. Leashed dogs are also welcome in many outdoor areas of Navy Pier, making it a fun stop to enjoy the waterfront atmosphere and seasonal events. If shopping is on your itinerary, take a walk along the Magnificent Mile, where many stores welcome well-behaved dogs.
When it's time to grab a bite to eat, Chicago has no shortage of dog-friendly patios. Fido is welcome at outdoor tables at Bar Siena, a dog-friendly restaurant featuring Italian street food, pizza, and drinks. They even have a dog menu where pups can order chicken, a burger patty, steak, gelato, a dog doughnut, and even a pup sundae! Fido is also welcome at the outdoor tables at The Perch Kitchen and Tap, where pups can enjoy options from the dog menu, including the Puppy Power Bowl, a Pupsicle, or even a Hefe-Woof-Zen drink. For humans, this restaurant and brewery serves wood-fired grill favorites, sandwiches, burgers, and vegetarian options, along with a full bar and weekend brunch. Throughout the city, you'll also discover numerous breweries, cafés, and neighborhood restaurants that happily welcome four-legged guests on their outdoor patios.
Before heading out each day, pack a collapsible water bowl, plenty of fresh water, waste bags, and a leash. During the warmer months, be mindful of hot sidewalks, and always keep your dog hydrated. Be sure to keep your dog leashed except in designated off-leash areas, and always clean up after your pet so everyone can enjoy Chicago's beautiful parks and public spaces.
From splashing along the shores of Lake Michigan to strolling the scenic Riverwalk and relaxing on a dog-friendly patio, Chicago offers endless opportunities to explore with your four-legged companion. Whether you're visiting iconic attractions or uncovering hidden neighborhood gems, you'll find plenty of pet-friendly experiences that make every outing memorable.
So pack the leash, grab a few treats, and get ready to discover why Chicago is one of the best cities for a dog-friendly getaway. The memories you make together are sure to last long after your trip comes to an end.
Paws Rest Here
Luie Boone had paw-selected this perfect vacation rental for your stay in Chicago, Illinois. Check it out below!
Rental Name: BoHo House
This rental has 3 bedrooms with 4 beds and 1 bath.
Photos by AIRBNB.com and VRBO.com
It features the following amenities:
Charming, airy bohemian gem built in 1903
Located in hip Avondale Neighborhood on the border of Logan Square and Avondale
Private, fully fenced backyard with string lights and cozy seating
Gas grill for BBQs (gas included)
Fire pit
Pet-friendly! Let your pup roam safely
What would Luie Boone have thought of this rental? He would have woofed:
My humans had planned a special family vacation to Chicago, and they found a place they knew I would have loved—BoHo House. The moment they saw it was pet-friendly, I could tell they were picturing me there, making memories right alongside them.
The private, fully fenced backyard would have been my favorite part. I imagined running through the grass, sniffing every corner, and relaxing nearby while my humans enjoyed the patio, grill, string lights, and cozy fire pit. Other pups who stayed there had loved it too, with their families saying the backyard was the perfect place for dogs to safely play, relax, and enjoy being outdoors. They were excited to visit Chicago, home of the Chicago Bears. My human Dad was a big Green Bay Packers fan, so being in Bears country definitely wouldn't have changed his loyalty! But he still would have enjoyed exploring Chicago and taking in all the fun activities the city had to offer. And I know I would have brought one of my favorite stuffed bear friends, Bear Bear, along for the adventure. He was one of my little buddies, and I know he would have loved exploring Chicago with me and sitting by my side at BoHo House. Sadly, I passed away before we could take that trip. My humans decided they couldn't go without me because I was part of their family, and the trip just wouldn't have felt the same. Even though I never got to make the trip, I know I was part of their plans, their memories, and their hearts. The best adventures were never about where we went—they were about being together.
Paws Venture Here
Luie Boone had sniffed out and dug up these local gems for you to check out while vacationing in Chicago, Illinois!
Mercury's Canine Cruise
Traveling to Chicago with your dog?
Mercury's Canine Cruise offers a unique way to explore the city’s famous skyline while keeping your four-legged companion part of the adventure.
This seasonal sightseeing cruise travels along the Chicago River and Lake Michigan, giving visitors stunning views of Chicago’s iconic architecture, historic bridges, and beautiful waterfront from the comfort of the boat.
Designed with both pets and their people in mind, Mercury's Canine Cruise welcomes leashed dogs aboard and provides thoughtful amenities like water bowls and a designated pet relief area. It’s a relaxing way to take in the sights, learn about Chicago’s history, and enjoy quality time with your pup without having to leave them behind.
For visitors traveling during the fall season, the Howl-O-Ween Canine Cruise adds an extra touch of fun. Dogs and their owners are invited to dress up in costume and enjoy a festive cruise filled with seasonal spirit, adorable photo opportunities, and plenty of wagging tails.
Whether you’re planning a weekend getaway, a city escape, or a pet-friendly vacation, Mercury's Canine Cruise is a must-do Chicago experience. Enjoy the fresh lake breeze, capture unforgettable skyline photos, and make memories exploring one of the city’s most popular attractions with your best friend by your side.
The 606
If you're exploring Chicago with your dog, The 606 is a must-visit destination.
This 2.7-mile elevated trail, built on the former Bloomingdale Railroad Line, offers beautiful city views, colorful public art, and plenty of space for you and your pup to enjoy a walk together.
The trail's history dates back to the years following the Great Chicago Fire of 1871, when freight trains used the railway to transport goods across the growing city
After the railroad was abandoned in the 1990s, the community transformed it into the vibrant green space that opened in 2015.
Its name, "The 606," comes from Chicago's famous ZIP codes, symbolizing its connection to the city's neighborhoods.
Today, The 606 winds through Wicker Park, Bucktown, Logan Square, and Humboldt Park, making it a favorite for locals and visitors alike.
Dogs are welcome on leash, and the wide paths, gardens, and scenic overlooks make every walk an adventure. Pack a leash, water, and a few treats, then enjoy one of Chicago's most unique dog-friendly walks together.
LaBagh Woods
LaBagh Woods is one of Chicago's best-kept secrets for dog lovers looking to enjoy the outdoors.
Located on the city's Northwest Side, this beautiful forest preserve features scenic trails through woodlands, wetlands, and along the North Branch of the Chicago River, making it a perfect destination for a peaceful walk with your leashed pup.
The preserve is named after Ella LaBagh, a pioneering conservationist who played an important role in protecting Chicago's natural spaces. Originally known as Snell Woods, the area became part of the Cook County Forest Preserves in 1922 and was renamed in her honor in 1940.
Today, LaBagh Woods is recognized as one of the area's top birdwatching spots, with more than 200 bird species recorded, along with deer, turtles, butterflies, and other native wildlife.
Dogs are welcome throughout the preserve as long as they remain on a leash.
Bring water, waste bags, and sturdy shoes, as some trails can become muddy after rain.
Staying on designated paths and keeping your dog leashed helps protect the preserve's wildlife while ensuring everyone can enjoy this peaceful natural escape.
With its rich history, abundant wildlife, and beautiful natural scenery, LaBagh Woods is a fantastic place to spend quality time outdoors with your dog.
Caldwell Woods
Just a short distance from LaBagh Woods, Caldwell Woods offers another peaceful escape into nature on Chicago’s Northwest Side.
Located along the North Branch of the Chicago River, this scenic forest preserve is part of the larger North Branch Trail system, making it a wonderful addition to a day of exploring Chicago’s beautiful outdoor spaces with your pup.
Named after Billy Caldwell, also known as Sauganash, a Potawatomi leader, interpreter, and diplomat, Caldwell Woods carries a connection to Chicago’s early history. Today, this tranquil area invites visitors to enjoy its mature woodlands, shaded trails, and natural surroundings while discovering a quieter side of the city.
Leashed dogs are welcome throughout the preserve, where curious pups can take in the many sights, sounds, and scents of the forest. Dogs that enjoy a leisurely stroll, a longer walk, or simply exploring new surroundings will love the relaxing outdoor experience Caldwell Woods provides away from the busy city streets.
Dan Ryan Woods
Dan Ryan Woods on Chicago’s South Side is a perfect escape for dogs and their humans, offering wooded trails, open spaces, and plenty of new scents to explore.
With its towering oaks, rolling hills, scenic stairs, and peaceful paths, it feels like a natural retreat hidden within the city.
One of the best parts of a visit is exploring the winding trails, climbing the historic staircase, and walking the path along the river, where dogs can enjoy new sights and smells while their humans take in the peaceful surroundings.
The changing terrain makes every walk feel like a small adventure.
This beautiful forest preserve is also a walk through Chicago’s ancient past. Geologists refer to the area as part of “Blue Island,” a raised ridge of land that stood above the waters of ancient Lake Chicago thousands of years ago. As glaciers melted at the end of the Ice Age, much of the surrounding area was covered by water, while this higher ground remained above the lake like an island.
Today, dogs can explore a landscape shaped by glaciers long ago.
A visit to Dan Ryan Woods is more than just a walk—it is a chance to enjoy nature, discover Chicago’s history, and let your pup experience one of the city’s most unique outdoor treasures.
Ping Tom Memorial Park
If your dog loves walks with a view, Ping Tom Memorial Park is a Chicago destination worth exploring.
Located along the South Branch of the Chicago River in Chinatown, this waterfront park offers a relaxing escape with plenty of sights, sounds, and smells for your pup to enjoy.
The park’s walking paths are perfect for a leisurely stroll while taking in the skyline, river views, and passing boats. One of the highlights is the 18th Street Bridge, which offers a beautiful spot to pause, snap photos, and enjoy the scenery from above.
As you wander through the park, you’ll also find colorful murals that bring art and culture into the outdoor space. One standout piece is the mural Be Like The Water, which adds a meaningful and vibrant touch to the park while reflecting the creativity and spirit of the surrounding Chinatown community. Another beautiful piece, Between The Mountains and The Water, draws inspiration from traditional Chinese landscape imagery and highlights the connection between nature, water, and the environment. Together, these murals create a unique outdoor gallery and make a fun backdrop for photos with your four-legged friend.
Don’t miss the park’s iconic pavilion, inspired by traditional Chinese design. With its pagoda-style roof and peaceful riverfront setting, it’s one of the most recognizable features of Ping Tom Memorial Park.
With its mix of nature, art, architecture, and waterfront views, Ping Tom Memorial Park is a wonderful place to enjoy a dog-friendly adventure in Chicago. Grab the leash, pack some treats, and spend the day exploring this unique neighborhood gem with your pup.
Promontory Point
A lakeside favorite for both Chicago visitors and their four-legged companions, Promontory Point is a beautiful place to slow down and enjoy the city from a different perspective.
Located in Burnham Park, this peaceful peninsula welcomes leashed dogs and offers stunning views of Lake Michigan and the downtown skyline.
It’s a great spot for a leisurely walk, a relaxing break, or a photo opportunity with your pup.
Designed in the 1930s by renowned landscape architect Alfred Caldwell, Promontory Point is known for its unique limestone shoreline, grassy areas, and historic connection to Chicago’s celebrated lakefront parks.
Over the years, it has become a beloved gathering place for locals, photographers, and visitors looking to enjoy one of the city’s most scenic views.
Dogs will love exploring the walking paths and open spaces while taking in the sights and smells of the lakefront.
Be sure to bring water for your pup, especially on warmer days, as shaded areas are limited.
With its scenic walking paths, historic shoreline, and unforgettable skyline views, Promontory Point is a must-see Chicago destination where both visitors and their dogs can relax and enjoy the beauty of the lakefront.
PB&J: Pizza Beer and Jukebox
PB&J: Pizza, Beer & Jukebox in Chicago is a fun neighborhood spot where both humans and pups can enjoy a great outing.
Known for its handcrafted pizzas, refreshing beer selection, and classic jukebox vibes, PB&J offers a relaxed atmosphere perfect for a casual meal with friends, family, or your four-legged companion.
Dogs are more than welcome here, with a special menu just for pups featuring a Pupwich, PB&J Dog Biscuit, and house-made Doge Jerky.
While your dog enjoys a treat of their own, you can dig into delicious pizza, sip a cold beer, and enjoy the laid-back energy that makes PB&J a Chicago favorite.
Luie Boone's Pet Peeve about
Chicago, Illinois
There's just so much to love about this vacation destination, but there's one thing that would have put Luie Boone's leash in a twist and he would have woofed:
I always wondered about Chicago’s famous hot dog. Humans get very serious about it — especially about one little thing: ketchup.
I don’t understand why a simple red sauce causes so much debate. To me, food rules are easy: if it smells good, it deserves a closer look. But in Chicago, ketchup on a hot dog is a big no-no for many people. They say a true Chicago-style hot dog needs mustard, relish, onions, peppers, a pickle, and celery salt — but no ketchup. I may never have made it to Chicago, but I would have loved to sit nearby, watch the humans argue, and patiently wait to see if anyone dropped a bite. After all, dogs don’t judge toppings. We just appreciate the love that comes with sharing a meal.
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