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Roam: Stay, dine and play with your pup in Chicago

You and you pup can enjoy parks, cafes and beaches in dog friendly Chicago. If you’re looking for a vacation spot to share with your pooch, book a trip to the windy city!

Roam: Stay, dine and play with your pup in Chicago

Some people think Chicago is called the “windy city” because of the wintery gusts that blow off from Lake Michigan. Others insist it was nicknamed for local politicians who were full of hot air.

Either way, your dog won’t care, because Chi-town, as it’s also known, welcomes canines and their owners. In a survey posted on, it ranked fifth among the top ten, dog-friendly US cities.

Chicago Lodgings That Invite Your Dog to Sit and Stay

At the Alise Chicago, a Staypineapple boutique hotel in Chicago’s Loop district, a dog-friendly room comes with a dog bed, water bowl, treats and a baggie dispenser with bags, and they’re all yours to take home. While you’re there, tag your photos with #pineapplepups and ask the staff to post them on social media.

You’ll find all the creature comforts at the award-winning Radisson Blu Aqua Hotel, near Chicago’s Magnificent Mile and Millennium Park. The ViPup package, available for a limited time, offers overnight accommodations, a dog bed and dish, a toy, portable food and water bowl, waste bag dispenser, food and drink mat, and gourmet doggie treats. Book ahead for an optional one-hour photo shoot—appointments are limited. If your pup gets tired when you’re out for a walk, request a dog stroller, subject to availability

At the Dana Hotel and Spa, your best four-legged friend can join you for yappy hour on the outdoor patio. For a small fee, you can upgrade to a room with a doggie bed and bowls to use during your stay, an organic pet treat, and a collar tag keepsake. The concierge can book an in-room pup massage or send up a pet physic.

Playful Places to Take Your Pet in Chicago

Each year, the Chicago White Sox hold a “Dog Day,” so fans can bring their pups to the ballpark. In 2016, the team broke a Guinness World Record, with 1,122 dogs on hand, many sporting White Sox caps and chowing down on hot dogs.

For dog-welcoming parks, visit Windy City Paws, where you’ll find details and video tours. Amenities vary, but many offer separate areas for small dogs, drinking fountains, and seating for humans. Some, like Lake Shore East Dog Park, have fun water features for dogs.

When your pup is ready for a walk, snap on his leash and head to The 606, a path and trail system that runs through Logan Square and other neighborhoods around the former Bloomingdale rail line.

If Fido wants to make a splash, take him to Montrose Dog Beach, one of Chicago’s top off-leash dog areas. He’ll need a tag, available for a small fee from local veterinarians, and he must have a current license and all required shots. After he’s splashed in the water and rolled in the sand, clean him up at Mutt Jackson, a self-service dog wash located nearby.

Dining Out with Dogs in Chicago

Hundreds of Chicago area eateries welcome leashed dogs. Harry Caray’s Tavern, at Chicago’s historic Navy pier and other locations, allows pups on outdoor patios. The Four Moon Tavern, a pub in Roscoe Village, will pour your pup a bowl of fresh water while you enjoy a beverage or the daily special on the patio.

Clark Street Ale House, in the River North neighborhood, has a large beer garden open to canines and their people. The owners have known to host “dog parties” where everyone can socialize and nosh.

Order from the doggie menu at 312 Chicago, where on “Wagging Weekends” (Saturdays and Sundays from 11 a.m. to 2 p.m.) canines can feast on chicken and pasta, salmon with white rice, and peanut butter biscuits or “beefsicles” for dessert. You’ll dine on the patio of this Italian restaurant, located in the Loop.

There are many more places to discover in Chicago that will welcome your best fur-friend. Take his leash, and see what adventures await the two of you!

Lynn Coulter is owned by two rescue dogs—Molly and Miss Paws—and occasionally blogs at She’s also the author of three books and a freelancer who writes about travel, gardening and more. She and her husband live in metro Atlanta, where they cheer for the Georgia Tech Yellow Jackets and spend their money on dog biscuits.

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