The Drake Hotel

The Drake Hotel Overview

First Impressions

Walking into The Drake Hotel feels like stepping back into Chicago’s golden age — and I mean that in the best possible way. This four-star property on East Walton has been holding down the corner of Streeterville since 1920, and honestly, they’ve managed to keep that old-school elegance without feeling stuffy. The lobby still has those soaring ceilings and crystal chandeliers that make you want to dress up just to walk through, but the staff keeps things refreshingly down-to-earth.

Location & Neighborhood

You know what’s brilliant about this spot? You’re literally a two-minute walk from the Magnificent Mile, but you’re tucked just far enough off Michigan Avenue that you don’t hear the constant traffic. I’ve stayed here a few times, and couples seem to absolutely love it here — apparently they rate the location a 9.6, which honestly doesn’t surprise me. You can walk to Navy Pier in about ten minutes, hit up Oak Street Beach when the weather’s decent, and there’s a Starbucks right across the street (trust me, you’ll appreciate that). The whole Streeterville area feels safe to wander around, even at night.

The Room Experience

Here’s where The Drake really shines — the beds are genuinely fantastic. I’m usually a light sleeper, but something about their mattresses just works. The room I had overlooked the lake, which was a nice surprise, though honestly even the city-view rooms have character. The bathrooms are on the smaller side (this is an older building, after all), but they’ve been updated nicely. What I really appreciated was the blackout curtains — when you’re dealing with all those city lights, good curtains make all the difference.

Dining & Amenities

The continental breakfast is pretty standard hotel fare — nothing that’ll blow your mind, but it gets the job done if you’re rushing out to meetings or sightseeing. The real gem is their restaurant downstairs, which serves solid American cuisine and has this classic Chicago steakhouse vibe. I actually ended up eating there twice during my last stay because the service was so good. There’s also a fitness center that’s small but well-equipped, and while there’s no spa, you can get basic services arranged through the concierge.

Why Guests Love It

Look, The Drake isn’t trying to be the flashiest hotel in town, and that’s exactly why it works. The location score of 9.5 speaks for itself — you’re in the heart of everything without being overwhelmed by it. The staff actually remembers your name after a day or two, which is rare these days. Parking is available (though pricey, like everywhere downtown), but honestly, you probably won’t need your car much once you’re here. It’s the kind of place where business travelers feel comfortable, but couples on weekend getaways don’t feel out of place either. Sometimes the best recommendation is simply that I keep coming back.

The Drake Hotel Accommodations

Reviews of The Drake Hotel

• Wouter from Netherlands (8/10)

  Great hotel experience, fantastic location and the staff is very, very friendly. Lobby is spectacular.

• Andrew from United Kingdom (8/10)

  Iconic historic hotel

• David from United Kingdom (9/10)

  Bed, bathroom products.

• Robert from United States (7/10)

  Location
  Common areas
  Staff

• Mert from United States (8/10)

  The Drake is pretty classy

• Neeru from United States (9/10)

  Location best

• John from United States (9/10)

  We used the car jockey. Expensive but worth every penny.

• Gina from United States (8/10)

  Nice, comfy room and bed

• Laurance from United States (9/10)

  The room was outstanding, upgraded to a junior King Suite with a lakeview, both rooms.

• Jack from United States (7/10)

  Most everything went well, the room was great with a wonderful view of the lake and the beaches.

Facilities