Top Dog-friendly Activities in Chicago

We love our Pineapple Pups! All of our hotels are dog-friendly, so we jumped at the idea of partnering with freelance writer Dylan Moskowitz to provide A Dog Owner’s Guide To Chicago. Check out some dog-friendly things to do with your four-legged friend below, and check out Dylan’s blog for more insider tips!

Where to Stay - The Alise Chicago

The Alise Chicago-1504-Millennium Park View King Suite-Dog Bed Real Dog-3501x2335.jpg

The Alise Chicago is excited to offer every guest and their furpals our new Pineapple Pup Package that bundles our regular pet fee in with their room rate for extra savings. We’ve learned that helping pets and owners stick together when traveling creates happy guests, and happy guests is what Staypineapple is all about. To take advantage of this pawesome deal, book directly on!

Top Dog-Friendly Activities in Chicago

Millions of visitors flock to Chicago each year for the art attractions, dining and beautiful scenery. Whether you’re visiting for a couple of days or looking to move to “The Windy City,” it’s good to know what activities you can do with your four-legged friend.

You can spend a day at one of the many dog beaches, go on a stroll in the park and much more with your pet BFF. With so many fun activities, it’s no wonder Chicago was named one of the most dog-friendly cities in America by The Huffington Post along with New York and San Francisco.

You’ll definitely want to check out these exciting dog-friendly activities and destinations the next time you’re in Chicago:

Sandy Paws

Enjoy stunning views of the city while relaxing by Lake Michigan with your pup. With temperatures in the mid-80’s during the summer, there’s no better place to take a dip with your dog.

Montrose Dog Beach and Belmont Harbor Beach are two popular sandy beaches within the city that welcome dogs of all sizes. Montrose Dog Beach has 3.83 miles of closed-in space that is perfect for larger dogs to roam, while Belmont Harbor Beach has a separate section specifically for smaller dogs.

Both Montrose Beach and Belmont Harbor Beach have a separate area for dogs that is off-leash, making it the “paw-fect” place to cool off. Be sure to get the $5 required Dog-Friendly Area (DFA) tags for your dog beforehand. These tags can be purchased at veterinary offices throughout Chicago and must be renewed annually.

Cruise Through the City

From street musicians to concert halls and more, there’s so many things to do and see in Chicago. A tour of the famous Chicago River is a good place to start in order to get your bearings of the city. Several tours welcome dogs, however, the Chicago Seadogs Cruises specialize in making your furry friend welcome.

History buffs will love the thrilling architecture tour, which passes by the Tribune Tower, Lyric Opera and more famous Chicago sites. Leaving from Chicago’s Navy Pier, this 75-minute tour starts allows dogs!

Be sure to call ahead to make sure there is room on the boat for your dog(s). If you’re feeling more adventurous, try the extreme thrill ride tour on a jet boat. This jet-propelled ride reaches up to 45 mph and includes 360 degree spins in the Navy Pier. Bring ponchos for you and your dog because you will get wet on this tour!

Head to the Park or the Pier


Chicago has dog parks dispersed throughout the city perfect for a doggie playdate. Check out Wiggly Field Dog Friendly Area, Chicago’s first official dog exercise and play area.

You can also take the pups to Navy Pier for one of the most pet-friendly areas in the city. Navy Pier is over 3,330 feet long filled dog-friendly restaurants, shops and activities.

Harry Caray’s Tavern is one of the most popular restaurants on the pier to bring your dog or try the food court for more options. Other delicious dog-friendly restaurants in the city include Begyle Brewing Company and Parson’s Chicken & Fish.

After a stroll along the pier, head to Millennium Park for a selfie with the famous Cloud Gate sculpture, better known as “the bean.” Pets aren’t allowed in the park, however, there is a good view of the sculpture by the McCormick Tribune Ice Rink.

Soak in the Sights by the River

The Chicago Riverwalk is a four-mile pathway that parallels the Chicago River on the south side of the city.

Whether you’re visiting in the summer or winter, the Riverwalk is the perfect place to walk your dog and take in the sights. Be sure to drop by one of the shops mentioned below to prepare for cold temperatures with your pet.

Shop ‘Til You Drop

With many dog-friendly activities in Chicago being outdoors, you may want to escape the elements and get some shopping done. From big-name stores to local boutiques, there are quite a few shops in the city that welcome and even cater to pets.

Get a warm coat for your stylish pup at Doggy Style Pet Shop. Then, head to Bloomingdale’s or Nordstrom with your dog for some style of your own. Finish out your night at Archie’s Iowa Rockwell Tavern for board games, free pool and more fun with pets and friends! From public art to stunning views of the lake, this trip will be unforgettable for both you and fido.

If these fun dog-friendly activities don’t make you want to book a trip to Chicago, then you’re barking up the wrong tree. With the city being named one of the top destinations for pets, there’s really no reason not to book a trip to Chicago soon!

Follow us on social media: