Dear Chicago, you'd be surprised to know that we never consider you the "Second City" at all. Anyone who has taken the architecture tour can see that this nickname doesn't do justice to your greatness compared to your Big Apple rival. In light of Chi-Town’s glimmering summer season, we’ve curated a list of the eight best boutique hotels to stay at so you can experience firsthand why the “Windy City” is a favorite destination year-round (and, dare we say, America’s best metropolis?).
The Robey
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Key Points:
- Website
- 4 Stars
- Rooms: 89
- Chicago Midway International Airport (MDW)
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Amenities:
- Outdoor pool
- Free WiFi
- Fitness center
- 5 Bars & Restaurants
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The Robey, housed in the former Northwest Tower, transcends its original 1929 office bones, lobby, and rooftop spaces into understated elegance, thanks to Belgian design duo Nicolas Schuybroek Architects and Marc Merckx Interiors. Its 89 rooms divide into two distinct forms: the “Tower Rooms,” sporting unique triangular footprints that invite ample sunlight and warm hardwood floors, and the “Annex Lofts,” which evoke an urban warehouse vibe with bunk beds and polished concrete finishes.
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BOOK WITH US FOR PERKS
- VIP status
- A welcome card from the GM
- Daily breakfast for two
- Special amenity or local experience worth min €50 per stay on guestrooms and €100 per stay on suites
- Room upgrade subject to availability
- Early check-in/late check-out subject to availability
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Pendry Chicago
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Key Points:
- Website
- 4 Stars
- Rooms: 364
- Chicago Midway International Airport (MDW)
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Amenities:
- Fitness center
- Rooftop bar
- 24-hour front desk
- 4 Bars & Restaurants
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Nestled within the iconic Art Deco Carbide & Carbon building, a 37-story marvel gracing Chicago's renowned Michigan Avenue, the Pendry Chicago stands as a beacon of modern luxury. The rooms and suites showcase a classic monochrome palette intertwined with authentic 1920s fashion. Sweeping views of the Chicago River and Michigan Avenue peek through bay windows, allowing natural light to shine through. Downstairs, the lavish Bar Pendry exudes a swarthy-toned, classic lobby bar vibe, perfect for a nightcap (or two) after a night out on the town.
The Publishing House
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Key Points:
- Website
- 5 Stars
- Rooms: 11
- Chicago Midway International Airport (MDW)
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Amenities:
- Free WiFi
- Breakfast
- Bar
- 1 Bars & Restaurants
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The Publishing House, West Loop's premier B&B, resides in a stately three-story brick building dating back to 1909. This design-forward home seamlessly blends old and new: gemstone-colored tufted velvet couches, contemporary dining sets, and unique light fixtures create cozy seating areas, while vintage art arranged in gallery-wall formation adds to the bed-and-breakfast charm. Word has it that the breakfast is exceptional, offering dishes like poached eggs with smashed sweet potato and crispy kale.
Thompson Chicago
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Key Points:
- Website
- 4 Stars
- Rooms: 247
- Chicago Midway International Airport (MDW)
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Amenities:
- Free WiFi
- Fitness center
- Pet friendly
- 2 Bars & Restaurants
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Poised in the heart of Chicago’s Gold Coast, the Thompson Chicago provides a posh retreat for a restful night's stay. Sophistication defines its 247 guestrooms, where mid-century modern furnishings, bespoke artwork, sumptuous bedding, and en suite bathrooms with rainfall showers ensure a luxurious stay. To taste local life, guests can opt for one of the two-story penthouse suites hosting floor-to-ceiling windows, giving way to picturesque views of Lake Michigan and the cityscape below.
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BOOK WITH US FOR PERKS
- Welcome Amenity
- Complimentary Daily Breakfast for 2 per bedroom
- Property Credit
- Room Upgrade (subject to availability)
- Early Check In (subject to availability)
- Later Check Out (subject to availability)
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The Hoxton, Chicago
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Key Points:
- Website
- 4 Stars
- Rooms: 182
- Chicago Midway International Airport (MDW)
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Amenities:
- Outdoor pool
- Room service
- Free WiFi
- 2 Bars & Restaurants
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The Hoxton, Chicago, stands in the West Loop’s trendy Fulton Market District as a stylish, mid-century modern haunt for locals and visitors alike. This 182-key hotel has 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 remainder of their stay if they so desired, but the up-and-coming area is all too enticing to resist exploring.
Chicago Athletic Association
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Key Points:
- Website
- 4 Stars
- Rooms: 240
- Chicago Midway International Airport (MDW)
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Amenities:
- Fitness center
- Free WiFi
- Room service
- 5 Bars & Restaurants
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Situated directly across from Millennium Park (yes, the one with The Bean), the Chicago Athletic Association is a historic landmark turned luxury hotel. The debonair rooms feature vintage-inspired custom upholstery and masculine touches like dark hardwood accents and Carrara marble bathrooms. Downstairs, the authentic Drawing Room invites guests to dine and drink as if they were stepping back into the 1890s.
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BOOK WITH US FOR PERKS
- Welcome Amenity
- Complimentary Daily Breakfast for 2 per bedroom
- Property Credit
- Room Upgrade (subject to availability)
- Early Check In (subject to availability)
- Later Check Out (subject to availability)
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The Guesthouse Hotel
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Key Points:
- Website
- 4 Stars
- Rooms: 25
- Chicago Midway International Airport (MDW)
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Amenities:
- Free WiFi
- Spa
- Fitness center
- 0 Bars & Restaurants
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The Guesthouse Hotel is often hailed as one of the Windy City’s coolest stays, and it’s easy to see why. Inside, the Clubroom blends classical and midcentury-modern design with crystal chandeliers, leather and velvet furnishings, and sleek concrete floors. Its one-, two-, and three-bedroom suites offer fully equipped kitchens, relaxing living areas, and private balconies so guests can take advantage of downtown like the locals do.
Viceroy Chicago
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Key Points:
- Website
- 4 Stars
- Rooms: 180
- Chicago O'Hare International Airport
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Amenities:
- Outdoor Pool
- Fitness center
- Room service
- 1 Bars & Restaurants
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Housed in a 120-year-old landmark, Viceroy Chicago seamlessly blends past and present from the inside out. An Art Deco flair comes to life, from the striking 18-story glass tower façade to the geometric-patterned artworks and swarthy-toned color palette in the rooms (think: maroon, medallion yellow, and teal green). For spectacular views of Lake Michigan, the rooftop pool is the place to be during Chi-Town’s best time of year.
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