Dear Chicago, you might be surprised that we never refer to you as the “Second City.” Anyone who has ever been on an architecture tour knows that moniker doesn’t do justice to your grandeur compared to your Big Apple rival. With Chicago’s summer season in full swing, we’ve compiled a list of the eight best boutique hotels so you can experience firsthand why the Windy City is a popular year-round destination (and, dare we say, America’s best metropolis?).
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• Website |
Equipment:
• Outdoor pool |
Housed in the former Northwest Tower, Robey transforms its original 1929 office buildings, lobby and rooftop spaces into understated elegance thanks to Belgian design duo Nicolas Schuybroek Architects and Marc Merckx Interiors. Its 89 rooms are divided into two distinct forms: the “Tower Rooms,” with their unique triangular floor plan that lets in plenty of sunlight and warm hardwood floors, and the “Annex Lofts,” which evoke an urban warehouse atmosphere with bunk beds and polished concrete surfaces.
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• Website |
Equipment:
• Fitness center |
Located in the iconic Art Deco building Carbide & Carbon, a 37-story marvel on Chicago’s famous Michigan Avenue, Pendry Chicago is the epitome of modern luxury. Rooms and suites showcase a classic monochrome color palette interwoven with authentic 1920s fashion. Stunning views of the Chicago River and Michigan Avenue are offered through bay windows that let in plenty of natural light. On the ground floor, the spacious Pendry Bar exudes the atmosphere of a dark, classic 1920s lobby bar, perfect for a nightcap (or two) after a night on the town.
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• Website |
Equipment:
• Facilities for guests with disabilities |
The Publishing House, West Loop’s premier B&B, is housed in a stately three-story brick building built in 1909. This design-focused establishment seamlessly blends old and new: jewel-toned tufted velvet sofas, modern dining table sets, and unique light fixtures create cozy seating areas, while vintage art in graceful gallery walls adds to the bed and breakfast’s charm. Breakfast is said to be exceptional, featuring dishes like poached eggs with smashed sweet potatoes and crispy kale.
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• Website |
Equipment:
• Free WiFi |
Located in the heart of Chicago’s Gold Coast, Thompson Chicago offers a posh retreat for a restful night’s sleep. Elegance reigns supreme in its 247 guest rooms, where mid-century modern furnishings, custom artwork, luxurious linens and private bathrooms with rain showers ensure a luxurious stay. To experience local life, guests can opt for one of the two-story penthouse suites with floor-to-ceiling windows that offer stunning views of Lake Michigan and the cityscape below.
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• Website |
Equipment:
• Outdoor pool |
Located in the West Loop’s trendy Fulton Market District, The Hoxton, Chicago is a stylish, mid-century modern hangout for locals and visitors alike. This 182-room hotel offers everything a guest could need: a co-working space, two restaurants (Cabra and Cira), a speakeasy cocktail lounge (Lazy Bird), a fitness center, a HOXSHOP boutique, and a rooftop pool. Guests could check in and not leave for the rest of their stay if they so chose, but the up-and-coming area is too tempting to resist exploring.
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• Website |
Equipment:
• Free WiFi |
Located directly across from Millennium Park (yes, the one with The Bean), the Chicago Athletic Association is a historic landmark converted into a luxury hotel. Elegant rooms feature custom-made, vintage-inspired upholstery and masculine touches like dark hardwood accents and Carrara marble bathrooms. On the ground floor, the authentic Drawing Room invites guests to dine and drink as if they were traveling back to the 1890s.
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• Website |
Equipment:
• Free WiFi |
The Guesthouse Hotel is often hailed as one of the Windy City’s coolest places to stay, and it’s easy to see why. Inside, the Clubroom blends classic and mid-century modern design with crystal chandeliers, leather and velvet furnishings, and sleek concrete floors. One-, two-, and three-bedroom suites offer fully equipped kitchens, relaxing living areas, and private balconies, so guests can enjoy downtown like a local.
| Important points:
• Website |
Equipment:
• Outdoor pool |
Housed in a 120-year-old building, the Viceroy Chicago seamlessly blends past and present inside and out. From the 18-story glass tower’s striking facade to the geometrically patterned artwork and dark-toned color palette in the rooms (think maroon, medallion yellow, and teal), an Art Deco flair comes to life. For spectacular views of Lake Michigan, the rooftop pool is the place to be during Chicago’s most beautiful season.
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