A Weekend in Dog-Friendly Chicago

Posted by Erin Ballinger

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 with Fido, from walks on the beach to dining alfresco at Navy Pier. The city also plays host to many dog-friendly events throughout the year. You won’t be able to squeeze it all into just one trip, but you can have fun trying!


Virgin Hotels Chicago spoils your pup with in-room amenities just for pets. Photo by @summer_thegoldenpup

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 this lucky pup:

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.

Leashed pups are welcome at most outdoor common areas at Navy Pier.Photo by @citymom0f3

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.

“Can I have a french fry? Pawlease!”Photo by Harry Caray's Tavern on the Pier

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 Navy Pier Beer Garden.


"Just water for me, please. I already ate." Photo by @wishbonechicago

8 a.m. Breakfast at Wishbone

Start off the day with a big Southern-style breakfast with your dog on the patio of Wishbone. 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 for your pup, order the Doggie Ice Cream flavored with real bacon, peanut butter and sweet potatoes.

See Chicago from the water on a boat tour just for dogs and their owners!Photo by @chicagodoglola

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 $44 for adults, $20 for kids ages 5-15, and are free for children under age 5. Fido floats for $10.

“I’ll have one of each, please.”Photo by Barrio

1 p.m. Lunch at Barrio

Refuel at Barrio during Bottomless Brunch, located in the River North neighborhood. While you dine on Fried Chicken and Churros, your furry friend can chow down on the patio, too! The pet-friendly restaurant’s Barkio Puppy menu features grilled chicken, a hamburger patty, skirt steak and dairy-free “woof” cream.

Shop ‘til Fido drops (and needs to be carried).Photo by @verifiedvalentino

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.

Big Star is well-loved by Chi-Town canines!Photo by @bigstarchicago

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.

Belly up to the bar and belt out some tunes at Four Treys Tavern.Photo by @pnic1013

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.


Dogs can join you at Miss Ricky’s for a yummy breakfast. Photo by @virginhotelschi

8 a.m. Breakfast at Miss Ricky’s

Located in the hotel lobby, pets will love this diner’s scenic patio. Dig into classic breakfast comfort food like pastrami-smoked lox with an everything bagel and all the fixins or the Morning Naples Pizza. Split a side order of turkey sausage with your four-legged friend to start his final day of vacay with an indulgent treat.

Fido can meet new friends at this dog beach.Photo by Facebook.com/MonDogBeach

10 a.m. Play at Montrose Dog Beach

Let your pup splash in the waters of Lake Michigan at 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.

Soak up the sun on Cafe Brauer’s dog-friendly patio.Photo by @vp.properties

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 Texas French Toast and breakfast burritos, and enjoy a great view of the Chicago skyline. Order a side of bacon if you want to get a treat for your good boy.

Fido can’t leave Chicago without a souvenir!Photo by Facebook.com/tailsinthecity

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.

Have you been to Chicago with your dog? Leave a comment or tweet us @BringFido!

Banner photo by Page Light Studios.