Pack your pup's bones and travel to the big city, actually the third-largest city in the U.S., for a weekend getaway to dog-friendly Chicago. There’s so much to do in the Windy City during the summer, from walks on the beach to dining alfresco at Navy Pier with your pooch. It's also festival season, headlined by the Chicago Blues Festival in June, Pitchfork in July and Lollapalooza in August for humans, and a host of dog-friendly events for Fido. You won’t be able to squeeze it all into just one trip, but you can have fun trying!
4 p.m. Virgin Hotels Chicago
To find your room at Virgin Hotels Chicago, just look for the porcelain watchdog standing guard outside your (and every other pet-friendly) room. Pets of all sizes stay for free and are given treats, a loaner bed and a red Virgin Hotels bandana. Celebrating a special day? The hotel will even plan over-the-top events for your four-legged friend. Check out the birthday party they threw for Porter:
After you've settled in, grab Fido's leash, leave the hotel and enjoy a 25-minute walk along the Chicago Riverwalk to your first destination.
6 p.m. Navy Pier
Navy Pier is often referred to as Chicago's lakefront playground. Bring Fido with you as you explore this popular dining, shopping and entertainment destination. Both locals and visitors agree that the pedestrian south dock is one of the best boardwalks in America. Stroll with your pup along the 2,000-foot-long walkway connected to the Pier and you’ll pass several dog-friendly restaurants, bars and activities.
7 p.m. Dinner and a Show
Located near the main entrance of the pier, Harry Caray’s Tavern Navy Pier offers a pet-friendly patio where you can dine with your dog. Smoked barbecue is the specialty here, and you can wash it down with one of several local craft beers on tap. Your pup can quench his thirst with water served in a souvenir bowl that you can take home. Afterward, listen to some live music with your canine companion at the lively Miller Lite Beer Garden.
8 a.m. Breakfast at Wishbone
Start off the day with a big Southern-style breakfast with your dog on the patio of Wishbone. This West Loop restaurant boasts a 5-bone rating on BringFido and was recognized by Eater as one of the 20 Essential Breakfast Spots in Chicago. Dogs will be given fresh water by employees wearing t-shirts featuring a picture of the owner’s beloved late poodle, Dolly, humorously snarling. For an indulgent treat, try the North Carolina-style Crab Cakes loaded with blue claw and lump crabmeat. It's topped with your choice of roasted red pepper or lemon butter sauce and served with eggs, grits and a biscuit.
10 a.m. Take a Dog-Friendly Boat Tour
Dogs on boats? Yes! Head to Mercury's Canine Cruise on the corner of Michigan Avenue Bridge and enjoy quality time with your pup while cruising Chicago's waterways. Sit back, relax and soak in the city on this 90-minute tour that covers Chicago’s rich history, architectural marvels and dog-friendly highlights. The boat has plenty of safe outdoor seating, water bowls and a special newspaper-lined restroom just for Fido. Tours are available on Saturday and Sunday from mid-July through early October. Tickets cost $36 for adults, $15 for kids ages 5-15, and are free for children under age 5. Fido floats for $8.
1 p.m. Lunch at 312
Refuel at 312 Restaurant, located in the pet-friendly Kimpton Hotel Allegro. While you dine on outstanding Italian fare, your furry friend can chow down, too! During #wagginweekends, 312 offers a dog menu featuring chicken and pasta, salmon with white rice, peanut butter biscuits, and frozen beefsicles.
3 p.m. Pet-Friendly Shopping Along The Magnificent Mile
Spend the afternoon getting some retail therapy at dog-friendly stores along Chicago’s famed Michigan Avenue. Make sure Fido minds his manners and follow these tips for a happy shopping experience with your pup. Peruse the goods at Nordstrom, The Shops at North Bridge and other stores along The Magnificent Mile with your furry friend.
7 p.m. Mexican Dinner in Wicker Park
Bring Fido to Big Star in Wicker Park to hang out on one of Chicago’s best dog-friendly patios. Nibble on chips and queso fundido and try creative tacos (all ordered from a walk-up window) in a cool, pet-friendly atmosphere. Drinks include American craft beer, Mexican cervezas and cocktails. When in doubt, a pitcher of margaritas is always a good decision! Of course, H2O is available for your pup.
10 p.m. Karaoke With Fido
Located in the heart of Chicago's Roscoe Village, Four Treys Tavern is a karaoke hotspot on Saturday evenings. Order a cold beer at this friendly dive bar and get ready to howl the night away (or just enjoy the show) with your canine companion. Well-behaved, leashed dogs are always welcome inside Four Treys.
8 a.m. Breakfast at Miss Ricky’s
Located in the hotel lobby, pets are always welcome at this diner’s scenic patio. Dig into classic breakfast comfort food like chicken and waffles or the on-trend avocado toast. Split a side order of turkey sausage with your four-legged friend to start his final day of vacay with an indulgent treat.
10 a.m. Play at Montrose Dog Beach
Let your pup splash in the waters of Lake Michigan at the Montrose Dog Beach. Fido can run free and play with other pups in the fenced, off-leash area. If you want to get a workout on the water, rent a dog-friendly kayak at Kayak Chicago or try stand up paddleboarding with your pup. All of the activity will help Fido relax on the trip home, too.
1 p.m. Lunch With a View
Dine at the dog-friendly Patio at Cafe Brauer, a historic Prairie School-style landmark located just south of the main zoo grounds in Lincoln Park. Munch on juicy burgers, crisp salads, hearty sandwiches, or brunch favorites like chilaquiles and pancakes, and enjoy a great view of the Chicago skyline. Order a side of bacon for $6 if you want to get a treat for your good boy.
2 p.m. Depart Chicago With Dog Treats
Make one last stop before you leave dog-friendly Chicago! Tails in the City offers freshly baked doggie donuts, cupcakes, cannoli and bonbons for the trip home. Browse the store’s selection of collars, leashes, clothing and dog beds to find the “pawfect” souvenir for your pup from your amazing weekend in the Windy City.