The Best Hotels in Chicago
By Jamie Dutton
Chicago’s hotel scene is an adventure worthy of a trip to the Windy City alone. From iconic skyscrapers to tucked-away gems, the city’s lodgings cater to every kind of traveler, from the lavish to the low-key. Here are five of the best hotels in Chicago that promise a stay as memorable as the city itself.
1. The Peninsula Chicago
The Peninsula Chicago isn’t just a hotel; it’s where you go to feel like a movie star. The service is so attentive that you’ll start to wonder if they’re reading your mind. The rooftop bar is the stuff of legends, with views that make you consider extending your stay indefinitely. If you’re feeling extra indulgent, the hotel’s spa offers a chocolate-themed massage. Yes, you read that right: chocolate. Just remember to save room for dessert at their restaurant afterward.
2. The Langham, Chicago
Walking into The Langham, Chicago feels like stepping into a sleek dream where everyone is better dressed than you. Perched right along the Chicago River, it boasts some of the best views in the city. The rooms come with floor-to-ceiling windows, which is perfect for people-watching or pretending you’re in a Hitchcock film. And the afternoon tea service? It’s the kind of experience that makes you wish your pinky finger was naturally more erect.
3. The Robey
Located in Wicker Park, The Robey is the kind of place you’d expect to find in Brooklyn, but better because it’s in Chicago. A converted Art Deco office building, the hotel blends history with a touch of hipster charm. The rooftop bar is a local favorite, perfect for Instagram shots that scream, "I’m cool, but not trying too hard." And if you’re really feeling yourself, you can rent one of their bikes and pretend you’re a local—just don’t forget which side of the lake is which.
4. The Drake
The Drake is what you imagine when you think of old Chicago glamour, where Marilyn Monroe sipped drinks and Sinatra might have crooned. The lobby is grand enough to make you feel like you’ve accidentally stumbled onto a movie set, which is accurate considering all the films shot here. Afternoon tea at Palm Court is a Chicago tradition, and it’s the perfect excuse to wear that fancy hat you bought for the Kentucky Derby and never wore again.
5. The Hoxton, Chicago
The Hoxton is for those who want a little London in their Chicago experience. With its lively common areas, it’s more of a social hub than just a hotel. The rooftop pool is ideal for pretending you’re in a music video, and the lobby is filled with enough hipster types to make you feel like you’ve walked into an influencer convention. But don’t worry, the rooms are blissfully quiet, allowing for a good night’s sleep after a day of exploring.
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Chicago’s hotel scene is an adventure worthy of a trip to the Windy City alone. From iconic skyscrapers to tucked-away gems, the city’s lodgings cater to every kind of traveler, from the lavish to the low-key.
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