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’re no strangers to Hilton Hotels. In fact, we’re a little partial to them (not sponsored… yet — Hilton, call us!) because of how reliably pet-friendly they are. The Drake was no exception. Located at the north end of Michigan Avenue, it’s not just steeped in elegance and old-school charm—it’s also wonderfully convenient for traveling with a pup.
Our room was spacious, the staff was warm, and best of all, there’s a small park directly across the street from the hotel’s back entrance—ideal for those early morning or late-night potty breaks with your four-legged travel buddy. No need to wander far or stress about finding green space in the middle of the city.
Bonus perk: If you’re a Hilton Diamond member, you’ll also get a daily food and beverage credit (we got $18 per day), which can be used at the hotel restaurant or the in-house market. Check your specific benefits before you book, as they may change over time.
Dog-Friendly Sights Near the Drake
The Drake’s location is a dream if you enjoy mixing upscale relaxation with easy access to Chicago staples. It’s a short walk to The 900 Shops, Water Tower Place, and yes… The American Girl Store—which my inner child could not resist visiting. 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 the trip: a dog-friendly architecture river tour with Shoreline Sightseeing! We went back and forth between this and the Seadog tour, but since it was Luna’s first time on a boat, we opted for Shoreline’s calmer cruise. (The Seadog includes a short speedboat ride at the end—we figured we’d save that thrill for another day.)
The ride was peaceful, the guide was funny and informative, and the views of the city from the water were stunning. Luna absolutely loved it—ears flopping in the breeze, eyes glued to other dogs sailing past. It was the perfect blend 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 how dog-friendly it can be. 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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