Nestled along Chicago’s glittering Gold Coast, The Drake Hotel is the epitome of classic Chicago hospitality — a beacon of old-school elegance that feels like stepping into a bygone era of glamour and grace. Opened in 1920 by John Drake and his sons as a luxurious East Lake Shore Drive landmark, this Beaux-Arts beauty has hosted legends from Frank Sinatra to Amelia Earhart, and even served as a WWII USO hub. With its storied past, The Drake isn’t just a hotel; it’s a slice of Windy City history that radiates an authentic, nostalgic vibe from every polished marble floor to its iconic brass details. Take a look at the photo above and you’ll get a sense of the classic vibe.
The lobby reinforces that vibe as soon as you walk in. A breathtaking expanse of crystal chandeliers, soaring ceilings, and intricate moldings, it’s a grand salon where afternoon tea feels like a ritual and live piano melodies set the perfect tone for people-watching. Service here elevates the experience — attentive staff with genuine Chicago warmth anticipate your needs, from seamless concierge recommendations to flawless check-in, making you feel like a VIP without the fuss. The hotel has plenty of energy and bustle, and you’ll probably see a wedding party or two if you’re there on the weekend.
Location-wise, The Drake is unbeatable: steps from the Magnificent Mile’s endless shopping on Michigan Avenue, with the glittering Lake Michigan waterfront just a short stroll away. Whether you’re diving into Nordstrom hauls or sunset walks along the lakefront trail, it’s the ideal launchpad for soaking up Chicago’s vibrant energy—from world-class museums to deep-dish delights. If you’re heading to Chicago with a female friend, The Drake offers a great choice, unless you’re both into the ultra-modern hotels.
Which brings us to the rooms. They’re undeniably comfortable with plush bedding, spacious layouts, and thoughtful touches like turndown service. But some friends noted they were a little musty and that’s not a suprise given the age of the hotel. I love the old school vibe, and that can lend itself to a very romantic vibe, but everyone’s taste’s vary. Many will appreciate the real charm of the old-school decor: think velvet accents, antique-inspired furnishings, and subtle Art Deco flourishes. It’s understated luxury that invites you to linger, evoking the golden age of rail travel and jazz lounges. If your partner gets all decked out for an evening on the town, returning to this room will heighten the experience.
In a city of skyscrapers and speed, The Drake offers a serene, sophisticated escape that’s perfect for first-timers or romantics. It’s more than a stay—it’s a love letter to Chicago’s enduring spirit. We’ll give this an enthusiastic 5 stars.
