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dogs deserve it favorite dog walking spots

Dogs Deserve It’s Favorite Dog Walking Spots

We feel very confident bringing you this blog post as we have traversed much of the city and have narrowed down our list of Dogs Deserve It’s Favorite Dog Walking Spots!

If you’re a dog parent who is looking to switch up your daily routine or want to enjoy the winter months exploring Chicago, then look no further! Check out our recommendations below.

North Side Must-See Dog Walking Spots

Dogs Deserve It is headquartered in Lincoln Park in Chicago. As such, that is where a majority of our clientele live. In the warmer months, we offer outdoor field trips which give our clients’ dogs an opportunity to discover beautiful parts of the city while enjoying a 4-5 hour trek! Here are our most frequented and favorite dog walking spots.

– Winnemac Park: Let your dog enjoy a day in this expansive and scenic park! According the Chicago Park District, Winnemac Park encompasses 22.38 acres and is bounded by Damen, Foster, Leavitt and Argyle. The park is full of greenspace and trails and can provide a leisurely and explorative day for your pup.

– Labagh Woods: Only a few minutes northwest of Lincoln Square, lies a beautiful, little known Forest Preserve. This trip is perfect option for dogs that love hiking in heavily wooded settings. Pups will enjoy the wildlife and animals abound in the forest!

South Side Must-See Dog Walking Spots

Granted, the love for dogs goes without saying! But, truly understanding dogs, body language and humane dog training methods is critical. A great dog walker will have received training that allows them to:

– Jackson Park: Most people don’t know that Jackson Park even exists, but sprawling an awesome 500 acres, this park is one of the prettiest in the city. Jackson Park is situated between Woodlawn and Hyde Park and is most known for its bird trails and its Garden of the Phoenix, a Japanese garden adorned with koi ponds and temple.

– University of Chicago: Your dog will love to explore this hidden gem! You can casually  traverse through the winding, lush University of Chicago and its glorious campus.

West Side Must-See Dog Walking Spots

– North Branch River Trail: The river isn’t only for kayaking! Dogs love to wander around the quiet North Branch River Trail. If your dog loves being near water and enjoys the shade then check out this spot.

The 606: This cool, elevated trail is a must see. Spanning from Ashland to Ridgeway, this trail passes through Bucktown, Wicker Park and other more unkown West Side spots. The landscaping is beautiful and is a nice chance to get a glimpse of our awesome city!

East Side Must-See Dog Walking Spots

– Old Town Historic Architecture tour: Does your dog prefer the city life? If so, they will adore the historical Old town Architecture tour. Getting lost in the cobblestone, winding roads of Old Town gives you a glimpse of Chicago history while enjoying a variety of different architecture styles. Your pups will love to explore hidden gardens, parks and quiet nooks all while being downtown!

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Make sure you read our previous blog on “Must-Have Gear for Dog Walking” before heading out into the cold. Strap on your heated layers and enjoy all the city has to offer!


Are you searching for a dog walker in the greater Chicago area? Dogs Deserve It is a Google 5-Star rated dog walking service with on-leash etiquette, advanced GPS tracking solutions that ensure accountability and an absolute LOVE for man’s best friend. Learn more about our dog walking services today.

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