There’s something magical about returning to a city you love and discovering it in a new way—especially when you’re exploring it with your dog by your side.
On our most recent trip to Chicago, Luna and I checked into the historic Drake Hotel, explored the city by boat, and soaked up summer moments in one of the best dog-friendly stays we’ve had in the Windy City.
Checking In: The Drake Hotel
We’ve stayed at our fair share of Hilton Hotels, and honestly, we’re a bit partial to them. Not sponsored, but Hilton, if you’re listening, we’re ready! They’re always so reliably pet-friendly, and the Drake was no different. Sitting right at the north end of Michigan Avenue, the hotel is full of elegance and old-school charm, plus it’s super convenient when you’re traveling with your pup.
Our room was spacious, the staff made us feel right at home, and the best part? There’s a little park just across the street from the hotel’s back entrance. It’s perfect for those early morning or late-night potty breaks with your four-legged travel buddy. No need to wander far or worry about finding a patch of grass in the middle of the city.
If you’re a Hilton Diamond member, you’ll get a daily food and beverage credit. We received $18 per day, which you can use at the hotel restaurant or the in-house market. Just be sure to check your benefits before you book, since they can change from time to time.
Dog-Friendly Sights Near the Drake
The Drake’s location is perfect if you love a little luxury mixed with easy access to all the Chicago classics. It’s just a short walk to The 900 Shops, Water Tower Place, and, of course, The American Girl Store. I couldn’t resist stopping in—my inner child was way too excited. Did anyone else grow up with an American Girl doll and feel like Coconut was their first dog? Just me?
If you’re shopping with your pup, remember most of these stores aren’t dog-friendly inside, but it’s still a beautiful area to window shop and stroll.
Dinner at Rosebud Steakhouse
After settling in, we headed out to dinner at Rosebud Steakhouse, one of our go-to spots near the Magnificent Mile. We didn’t bring Luna with us this time, but the restaurant does offer limited pet-friendly outdoor seating. Just make sure to call ahead and make a reservation, especially if the weather is nice!
We always recommend Rosebud if you’re looking for a classic Chicago steakhouse experience. The portions are generous (you’ll want to share the sides!), the service is excellent, and the vibe is cozy but refined.
Architecture Tour… By Boat!
This might have been the highlight of our trip: a dog-friendly architecture river tour with Shoreline Sightseeing! We debated between this and the Seadog tour, but since it was Luna’s first time on a boat, we picked Shoreline’s calmer cruise. The Seadog has a short speedboat ride at the end, so we decided to save that adventure for another day.
The ride was peaceful, the guide kept us laughing and shared so many fun facts, and the views of the city from the water were just beautiful. Luna was in her element, ears flopping in the breeze and eyes glued to every dog that sailed by. It was the perfect mix of sightseeing and relaxing, and we can’t recommend it enough if you’re visiting with your pup.
Final Thoughts
Chicago continues to surprise and impress us with its dog-friendliness. Whether you’re indulging in a little luxury at the Drake, admiring the skyline from the water, or just enjoying a stroll past historic landmarks, the city has plenty to offer two- and four-legged travelers alike.
Until next time, Chicago—thanks for another unforgettable adventure.
Paws and love,
Lauren & Luna 🐾
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