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Staypineapple, An Iconic Hotel, The Loop Chicago

Top-Rated Chicago Escape in the Heart of Stylish Downtown

Staypineapple, An Iconic Hotel, The Loop Chicago logo

Stay in the heart of Chicago’s thriving metropolis at the stylish Staypineapple, An Iconic Hotel, The Loop Chicago. Find the brand's cheeky signature yellow pineapple touches throughout this boutique hotel; from the pineapple-shaped welcome cookies to the emblazoned phone chargers and embroidered pillows. Visit Atwood restaurant and bar and order yourself a signature cocktail before hitting the town, then borrow a beach cruiser bicycle and cycle along the lake or simply spend your time exploring the city on foot.

Housed in a National Historic Monument building, smack-bang in the thick of the Chicago Loop, the hotel affords easy access to a plethora of eateries, shopping, cafés, theatres, parks and the Art Institute of Chicago. You’re only steps from the instantly recognisable Millennium Park, home to the Crown Fountain, The Bean and Jay Pritzker Pavilion. This chic hotel received a Tripadvisor Travellers’ Choice 2021 award, placing it among the top 10% of properties worldwide on the review site.

Luxury Escapes inclusions (select packages):
  • Refuel with US$10 food and drinks credit per person, per stay
  • Waived amenity fee, covering high-speed wireless internet, in-room coffee/tea and more
1 to 30 Nights packages available
Interest-free payment options available 
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Interest-free payment options available 
Klarna PayLatitude PayAfter Pay

package Options

Select duration
Deluxe Queen
Deluxe Queen
Comfortable and stylish, with those signature Staypineapple touches, these rooms feature a plush queen bed, city views and a modern ensuite
Size: 16
Members get access to exclusive rates
Option 1
Flexible Rate (inclusions valid for all guests)
  • Waived amenity fee for all guests (Wi-Fi, STREAMPINEAPPLE streaming service, in-room tea and coffee, unlimited bottled water and access to the hotel's beach cruisers)
  • US$10 food & drink credit per person, per stay
Deluxe King
Deluxe King
Panoramic windows afford gorgeous Chicago city views, while a generous king bed and 50” HD television greet you at the end of the day
Size: 16
Members get access to exclusive rates
Option 1
Flexible Rate (inclusions valid for all guests)
  • Waived amenity fee for all guests (Wi-Fi, STREAMPINEAPPLE streaming service, in-room tea and coffee, unlimited bottled water and access to the hotel's beach cruisers)
  • US$10 food & drink credit per person, per stay
Deluxe Two Queen
Deluxe Two Queen
These light-filled rooms offer double the fun with two ultra-comfy queen beds, panoramic windows with city views and a sleek ensuite
Size: 16
Members get access to exclusive rates
Option 1
Flexible Rate (inclusions valid for two)
  • Waived amenity fee for all guests (Wi-Fi, STREAMPINEAPPLE streaming service, in-room tea and coffee, unlimited bottled water and access to the hotel's beach cruisers)
  • US$10 food & drink credit per person, per stay
*Price is indicative and based on sample return fares (inclusive of booking fees on Low Cost Carriers). To view live pricing, conduct a full search. Luxury Escapes full Terms and Conditions apply
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