Who can resist this dog-friendly park with a name that's a fun play on the famous baseball stadium? Located in the Lincoln Park community, this park boasts doggie water fountains to keep dogs hydrated, waste bags to clean up after Fido and agility equipment for them to enjoy. Better yet, there is a small-dog enclosure specifically for diminutive dogs to frolic, so all dogs can live the big life together.

Want to enjoy the surf and sand with your furry buddy? Look no further than Dog Beach at Belmont Harbor. Here, a fenced-off area for dogs allows you to spend time with your dog by the water's edge. You can even play fetch and have your pooch go for a little dip in the water.

Bike, skate or walk this trail along with your dog. Located on the Northwest side, this trail is actually built over an old railway so it gives you a bird's-eye view of the surrounding neighborhood. Plus, its smooth surface is great for little paws.

Bring your dog wine tasting at this elegant wine shop that features a wide selection of red, white, dessert and other wines. They hold regular tastings with live music that your pup can attend with you. While he may not be able to partake of the libations, he'll be great company during your tasting.

If you're a budding entrepreneur, small business owner, freelancer or telecommuter, COCO is the place for you — and your pooch. This co-working space offers an office environment that stimulates your creativity with community work spaces, dedicated desks and access to conference rooms for a monthly fee. These work spaces are also pet-friendly, allowing you to bring Fido along for the day. And nothing's better than working alongside your furry friend.

Don't leave your pup at home — bring him along to this friendly neighborhood Irish pub where everyone will know your name and your pup's too. Located right on the Chicago River, this waterfront pub features an outdoor patio area that is dog-friendly so that your canine companion can enjoy some time out with you. You'll enjoy a lovely view of the river and the Navy Pier with your pooch while you enjoy their tasty edibles and drinks.

Stay in style with your pooch at this swanky downtown hotel. This boutique hotel has their very own "i am woof" program that offers an array of add-on amenities just for pooches. Here, pups can enjoy some sightseeing with their pet parents and then curl up on an in-room dana doggie bed when they return. Upon arrival, dogs receive a welcome bag, customized dog tag, gourmet treat and a special curated list of dog-friendly shops, parks and other attractions near the hotel. With amenities like doggie bowls in your room and add-on services including a pet psychic and in-room doggie massage upon request, pups enjoy hospitality at its finest.

Grant Park is home to Chicago's famous Buckingham Fountain and a fun dog park too — the Bark Park. Swing by the fountain with your pup on a leash to catch a glimpse of this famous landmark and visit the dog-friendly area to spend some time with him off-leash. The pup-friendly part of the park is located between Balbo Avenue and Roosevelt Drive in the South Loop. Here you'll find doggie drinking fountains, pooch waste bags and a bevy of tennis balls to entertain your furry buddy.