3 Days | 18 Miles
There's plenty for pups and their humans to do in Chicago. You can feel the lake breeze on your nose while taking a dog-friendly cruise. Let loose at one of the city's dog-friendly outdoor spots. Treat yourselves to some goodies from a doggie bakery, shop with your pup, and then put your paws up at a relaxing pet spa.
Make sure to check with attractions ahead of time for up-to-date operating hours, travel policies and health and safety information.
Treat your furry best friend to an exciting adventure-filled first day in Chicago. Stroll along Navy Pier where you can find unparalleled views of the city and all sorts of outdoor, dog-friendly dining patios, like Giordano’s and Harry Caray’s Tavern. You can even bring your dog on a thrilling Seadog Cruise to take in the city’s skyline. If your dog would prefer to take a more leisurely cruise, you can hop aboard Mercury Cruise’s Canine Cruise which departs from Michigan Avenue. Afterward, you can spoil your pup with a shopping spree down the Magnificent Mile where you can find dog-friendly stores such as Neiman Marcus and Bloomingdales. Stop into The Shops at North Bridge for more dog-friendly spots like Nordstrom.
Head toward the Chicago Riverwalk to discover a couple of dog-friendly patios for lunch, like O’Brien’s Riverwalk Cafe and the Chicago Brewhouse. Nearby, you can treat your dog at Goddess and the Baker, a chic café offering menu items like avocado toast, matcha lattes and even a layered rainbow cake for a fun dessert. Your dog can run off some energy and meet some new friends at one of downtown Chicago’s many dog-friendly parks including Grant Bark Park (inside Grant Park) and Bennett Park Dog Park in the Streeterville area. Permit required and available for purchase at participating local veterinarian offices. For dinner, head to one of the city’s most fun open-air restaurants, Recess, which is situated in the West Loop and known for its bright, lively space and delicious American fare.
Unlike many places, it’s not hard to find accommodating pet-friendly hotels in Chicago. At The Peninsula Chicago, pets receive beds, bowls and treats upon arrival and they share some dog park recommendations within walking distance. Loews Chicago Hotel was the first national hotel chain to launch a pet program that treats four-legged friends like VIPs (Very Important Pets) with amenities like a special pet room-service menu, pet toys and bedding, a list of local pet services and a welcome letter from the hotel’s general manager. Lastly, The Kimpton Hotels (Hotel Allegro and Hotel Monaco) are so pet-friendly they even have a Director of Pet Relations on-site at the hotel! So, it’s safe to say your pooch won’t feel like they’re sleeping in the dog house while in Chicago.
Kick off day two with a savory and sweet breakfast with your pup at Nilly Cafe, located near the iconic Millennium Park. Next, grab your doggie life jacket head to Montrose Dog Beach for a paddle excursion with Kayak Chicago. Another dog beach that your furry friend will love is Belmont Harbor Beach in the Lakeview area that welcomes dogs of all shapes and sizes.
Chicago’s nearby Lincoln Park features Wiggly Field Dog Park and walking paths throughout the area that offer scenic views in spots like the Nature Boardwalk. More trails throughout the city to take your pup include the Chicago Lakefront Trail (several locations in Chicago) and the 606 Trail that starts in the Bucktown area.
In nearby Wicker Park, you can discover more dog-friendly restaurants. Dog-approved spots include Paradise Park - a trendy, eclectic spot known for its fun outdoor patio and tasty pizza, along with Big Star - a locally-loved restaurant with a menu boasting Mexican street-food and refreshing margaritas. If you and your pup are on the go, you can track down the Fido to Go Food Truck - a mobile dog and cat treat food truck that provides updates on where it is in the city on its social media channels.
Your last day calls for some R&R for both you and your four-legged friend. After a hearty breakfast on the outdoor patio at Yolk in Streeterville, known for their fluffy pancakes and speciality juices, drop off your dog at one of Chicago’s notable pet spas like Paradise Pet Salon & Spa Too!, Inc. or Bucktown Bow & Meow which offers spa treatments like massages and grooming to rejuvenate your pup. Meanwhile, you can continue to discover all the shopping, food and views that the city has to offer!
There’s no better way to end a fun getaway with your pup than rewarding them with a tasty treat at one of Chicago’s delectable dog bakeries. Tails in the City, located in the Gold Coast area, offers peanut butter cups, doggie donuts and ice cream cones for pets, and Wigglyville, Inc. in Lakeview offers a wide assortment of pet treats.