We do our best, but it’s just not possible for us to cover every dog friendly destination in the country. That’s why we love receiving guest posts from our readers as they travel with their pets! Chicago is a popular pet friendly vacation destination and today Victoria Heckstall, a writer for The Go There Guide, gives us a look at the top five sites to see with your dog in the Windy City.


If ever there was a city that was made for dog lovers, then Chi Town is it! Chicago has been recognized as one of the most dog friendly cities, and choosing from it’s beautiful green neighborhoods and awe-inspiring parks is tough. To help you out, we have a list of the 5 best places to take your dog in Chicago! Just take note that dogs are not allowed on Chicago’s public transport system, with the exception of the water taxis. (GPF Note: Perhaps Chicago should take a look at Boston’s pet friendly public transit policy!)

White Sox Dog Day

A dog friendly baseball game may be a somewhat unusual outing, but one that is proving incredibly popular amongst dogs and their owners. Dogs seem to enjoy the excitement and atmosphere, and sharing a hotdog is sure to bring you closer together. Leashes and waste bags are obvious requirements, but apart from that, it’s just like taking your kids to a game. The White Sox are hosting two Dog Days at the Park this season, and the next one is on September 26th.

Lakefront Trail

One of Chicago’s main attractions is Lake Michigan, and what better place to enjoy it than from the Lakefront Trail? The path runs along the shore for 18 miles and connects various beaches and recreational amenities located along the lake.

Dogs on Lakefront - Chicago, IL
Credit: Chris Hamby

Navy Pier

This is a perfect place for a family outing, with great views and rich history to be discovered. But the best part about visiting Navy Pier is that you can let your pooch take a walk without a leash. The freedom and openness is refreshing, and the dogs really enjoy themselves. There’s something for everyone – shopping, eateries, rides and activities – and dogs on leash are welcome at most of the restaurants with outdoor seating, the outdoor seats at the food court, and on the Architectural Boat Tours that depart from the Pier.

Chicago River and Lake Michigan Boat Tours

For dogs who enjoy sightseeing as much as their owners do, welcome to Mercury Skyline Cruises! Every Sunday during the summer dogs are welcome to enjoy the 90 minute tour highlighting dog-friendly hotels, restaurants, dog parks, & fire hydrants. Pups may sit on your lap, in a seat, or on the deck, but be sure to keep them safe – having to dive in after your pooch would likely spoil the experience.

For everyone’s comfort, one restroom on the boat is for humans and one is lined with newspapers for pets. Before jumping right in (forgive the pun), gauge your dog’s readiness for this kind of outing – younger dogs and certain breeds are apprehensive around water and may not enjoy the experience.

Grant Park

This is the quintessential dog lovers’ paradise. An open, green park that is lush and full of life offers you the space that you need. Run, play catch, or just relax in the shade of a tree on a hot summer’s day.

Dogs in Grant Park - Chicago, IL
Credit: afunkydamzel

At the end of the day, you’ll find plenty restaurants where pets can join you on the patio and a great selection of pet friendly hotels in Chicago. Time to start making your travel plans!

This guest post is by Victoria, a freelance writer who writes for The Go There Guide.

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