Love Your Pets Day: Enjoy a Pet-Friendly Road Trip with Your Dog to Chicagoland (And Wisconsin, too!)

Feb 20, 2024

Let’s face it, if you’ve got pets you know that every day is Love Your Pet Day. However, that’ also means it is extremely likely that you’ll never turn down a reason to spoil your favorite companion a little bit extra on days like today! We’re sharing our love for all of our pet companions from small to large and celebrating with some great ideas for day trips and weekend getaways in the Chicago area and Wisconsin (especially the Milwaukee area.)

A gentle reminder: while it’s wonderful to take your companion animals everywhere you go, be mindful that there are some places that aren’t appropriate to bring your canine companion (or other well-trained pet) due to health codes or other regulations. Others may be restricted to service task oriented animals only, so please be mindful of store and business guidelines and check their websites or call to verify before bringing your canine companion or other animal with you.

Without further ado, here’s some wonderful pet-friendly places to put on your pet pal bucket list!

Best dog-friendly attractions in Chicago:

Mercury’s Canine Cruise
Seadog Cruises Chicago by Hornblower
Montrose Dog Beach
Chicago Riverwalk
Jackson Bark
Navy Pier
Midwest Coast Brewing Company
Puptown at MargatePark
Lake Shore Park
Chicago Lakefront Trail
Alarmist Brewing & Taproom
Begyle Brewing
Kayak Chicago

Dog Friendly Milwaukee Activities:

Milwaukee Boat Line
Lakeshore Paddle Sport Rentals
Salty Paws
Granville Dog Park
Black Husky Brewing
Lost Valley Cider Co
Milwaukee RiverWalk
Oak Leaf Trail
Broken Bat Brewing Company
Twisted Path Distillery
MOD GEN
Stigler Nature Preserve

Many restaurants may not allow canine companions or felines to join you for a meal due to health code regulations, but these special venues are designated pet-friendly!

Five Fabulous Dog-Friendly Chicagoland Area Eateries:

Barrio in River North is a popular Mexican restaurant with a special pup-friendly menu in a rustic-industrial chic setting! They offer a wonderful selection of specialty cocktails and expansive Mexican menu for humans, too.

Park & Field in Logan Square has a fantastic dog-friendly patio setup that’s just perfect for a Spring lunch date. You and your pup can lunch together in the sunshine! As you enjoy a handcrafted cocktail or craft beer and some games, your pet may chow down with a wonderful menu catered just to pups including a Bird Dog or Pooch Patty option with an exquisite Pup Cup for dessert.

Big Star on N Damen Ave has the perfect patio for your pooch to catch some rays while you sip on a signature margarita and some fine mexican food from the outdoor pick-up window. The restaurant loves dogs so much, in fact, they even have their own Instagram hashtag: #dogsofBigStar

Benchmark in the Old Town area is another fantastic pet-friendly spot with the best “bar food” in town, including six custom types of french fry, 10 types of wings, a plethora of beers on tap, delicious pizza and burgers, and more. Plus, they love pups so much your dog can choose from their house doggie menu. And don’t forget to document your doggie date, as the bar has its own dedicated hashtag #4CPatioPuppies, and they do gift card giveaways for the posts with hte most likes!

Howells & Hood in the heart of downtown Chicago is a surefire win for dining with your pup next to your side. You and your human companions can select from more than 100 craft beers, and enjoy a dish off their expansive menu including their signature Sweet Chili Chicken or Smoked BBQ ribs. If your pup requires a drink, too, you can ask your server for a water bowl and they’ll deliver it tableside for you!

Three Terrific Dog Friendly Eateries in Southern Wisconsin:

The Dog House Bar & Grill in Mt Horeb has a spacious outdoor patio that’s allows dog-friendly dining! Their Monster Burger is the stuff of legends, and we’re sure your dog won’t be sad if they get a tiny taste of it, too! (but not too much, because it’s very rich for pups!)

Grateful Shed in Wisconsin Dells is a standout due to the fact that it offers dog-friendly dining both inside and outside! With a variety of food trucks and cuisines to choose from, there’s definitely something for everyone to enjoy. Hang out with your friends and your pups and enjoy some fresh spring air and a delicious snack, no matter what your tastes are!

Riley’s Social House in Milwaukee is welcome to all your well-behaved canine companions whether you join in a local dog meet-up group or just a date for two (or three or four…we don’t blame you for collecting pups like potato chips!) It’s not just a dog friendly bar and restaurant in their outdoor space, but inside as well! The drinks and the dining are spectacular, and the owners gain high marks with dog lovers and dogs alike for their friendliness and cheer. What’s not to love?

Traveling with Fido overnight? Here’s some wonderful Dog-Friendly Lodging options to try while taking your next road trip together!

A Selection of Chicago’s Dog Friendly Stays:

The Guesthouse Hotel allows two dogs of any size in special pet-friendly rooms at no extra charge, and you’ll have your own canine concierge! As a special bonus, dog bowls and beds are available if needed, and it’s fine for dogs to be left unattended in rooms. It’s also very close to the biggest dog beach in Chicago, making it perfect for dogs who love some fun in the sun and sand!

The Emily Hotel allows big dogs, small dogs, and everything in between, and accommodates families with two dogs for a fee of $100 per stay. They’ll be treated like royalty at check-in with a designated grassy pet relief area, a special treat all their own, and beds and bowls at the front desk. The only request from housekeeping is that your dogs are crated when they enter the room for cleaning and restocking amenities.

Ray’s Bucktown Bed and Breakfast allows doggy guests of any size for an additional pet lodging fee of only $20 per night. Your furry friends will be well received at check-in with plenty of puppy cuddles, kisses, spare doggy bags, their very own treats, and water bowls or the room.

Just Some of Wisconsin’s Special Dog Friendly Hotels:

Justin Trails B&B Resort offers 200 acres of meadow and woodlands with three ponds, trails for on or off-leash adventures, and if your pup is extra friendly and well-mannered, they may enjoy a romp with the resident husky and llamas on the grounds! There is a small daily pet free as part of your lodging costs, but there are no weight restrictions on canine companions for suites or cabins.

Grand Geneva Resort and Spa allows 1 or 2 small canine companions in tow fo ra small pet fee, which includes a designated dog-in-room tag, a special food bowl, “Guest of Grand Geneva” collar tags for each pup, and a special clean-up packet for the pup relief areas.

The Iron Horse Hotel is a historic industrial warehouse turned hotel that offers incredible loft lodgings that are assuredly pet friendly. In fact, your dog will get their own in-room pet bed, bowls, gourmet treats, and more as part of the “Big Dog Special” package – they’ll even be welcomed on the special guest board in the lobby! Plus, you can get reccs from the front desk with local dog friendly areas and eateries!

The Jefferson Street Inn is so animal friendly that it once hosted the beloved animal handler Jack Hanna and his menagerie (including a tiger, snake, flamingo and penguin in tow!). You and your pup can book a pet-friendly accommodation for a small fee, and it includes a special welcome bag of treats for your furry friend as well as special pet dishes for your room!