Boats, Parks, and Paws: A Dog-Friendly Stay at The Drake in Chicago

Chicago is one of those cities that keeps getting better the more you explore it, and it turns out, it gets even better when you explore it by boat with a golden retriever who has strong opinions about other dogs on the river.

On this trip, Luna and I based ourselves at The Drake Hotel on the Magnificent Mile, took a dog-friendly architecture river tour, found a perfect little park right outside the hotel’s back door, and ate one of the better steaks in the city. Here’s how it went.

Checking In: The Drake Hotel

We’re partial to Hilton hotels — we’ve always had great experiences with them when traveling with Luna, and The Drake was no different. (Not sponsored. Hilton, if you’d like to change that, we’re ready.)

The Drake sits right at the north end of Michigan Avenue, and the location is genuinely ideal: historic architecture, spacious rooms, and a beautiful stretch of the city right outside the front door. After a day of adventures, the room felt like a proper retreat — the kind of place where you actually want to spend time between outings rather than just sleeping.

The practical detail that puts this at the top of the list for dog owners: there’s a park directly across the street from the hotel’s back entrance. No hunting for a patch of grass in the middle of the city, no long walks before coffee. It’s right there, which makes the early morning and late night routine considerably easier.

If you’re a Hilton Diamond Honors member, you’ll receive a daily $18 food and beverage credit usable at the hotel restaurant or the in-house market. Worth knowing before you book — and worth confirming, since benefits can change.

The Magnificent Mile (And One Detour)

The Drake’s location puts you within easy walking distance of the 900 Shops and Water Tower Place off Michigan Avenue. Most of the shops inside aren’t dog-friendly, but the stretch itself is a great area for a stroll — especially if window shopping counts as a workout.

I’d be remiss not to mention the American Girl Store at Water Tower Place, especially for anyone who grew up with the books and dolls the way I did. Coconut was my first “dog” — which, in hindsight, probably explains a lot about where Luna and I ended up. Luna waited patiently while I took longer than any adult should reasonably take in an American Girl store.

Dinner: Rosebud Steakhouse

We didn’t bring Luna to dinner on the first night, but Rosebud Steakhouse on the Magnificent Mile is worth calling out for anyone who does want to bring their dog — they offer limited pet-friendly outdoor seating. Call ahead and make a reservation if you’re planning to bring your pup, especially on good weather days, because outdoor spots fill up quickly.

The food is excellent: one of the better steaks in the city, and the sides are large enough to share with the whole table. It’s our go-to for a classic Chicago steakhouse experience on the north side of the city.

The Architecture River Tour (By Boat, With a Dog)

This was the clear highlight of the trip. We went back and forth between two options: Shoreline Sightseeing’s architecture river tour and the Seadog tour. We landed on Shoreline because it was Luna’s first time on a boat, and the Seadog includes a short speedboat stretch at the end of the tour — not the ideal introduction to boat life for a dog who had never done it before.

The right call. The Shoreline cruise is calm, well-paced, and genuinely enjoyable — the guide was entertaining, the city from the water looks completely different from the city at street level, and the breeze was perfect. Luna spent most of the tour stationed at the railing, ears going in the wind, eyes locked on every other dog she spotted on passing boats. She took to boat life immediately and without any caveats.

The Full Chicago Itinerary at a Glance

Planning a Chicago trip around the 4th of July? We’ve done that too — read about our dog-friendly Chicago 4th of July for a completely different angle on the city.