Day 1:
Chicago
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.