Staypineapple, An Iconic Hotel, The Loop
Staypineapple An Iconic Hotel The Loop offers a unique and dog-friendly experience, accepting any number of pets without size or weight restrictions. They even have pet-free floors for guests with allergies.
Friendly staff, clean and close to the redline.
We have stayed at the Stay Pineapple six times and have loved it every time. It is a beautiful old bank building in downtown Chicago and is close the everything.
The room was clean, comfortable. The staff was friendly. Food and staff always excellent.
A great selection of American favorites. PINEAPPLE QUICK BITES & BEVVIES are available! Salty, sweet, or savory? Luckily you won’t need to choose, because we offer a variety of snacks, beer, wine, and other refreshments. Simply ask an Everything Person at the front desk for assistance. IN-ROOM COFFEE AND TEA: Stay fueled with our signature blend coffee and tea for use with your in-room Keurig. We even have decaf if that’s more your style. More of your favorite is just a quick tap of the Everything Button away. PLUS...UNLIMITED BOTTLED WATER! Don’t be afraid to drink that bottle of water on the desk! Enjoy unlimited bottled water replenished daily in your room. Want more? Just use the Everything Button on your in-room phone.
Valet Parking only, Rates vary.
SURF PINEAPPLE, High-speed wireless Internet access on unlimited devices, so go ahead and use your computer, phone, and tablet anytime - all the time.
Contactless check-out is available
Cashless transactions are available
Essential workers only - NO
- Picasso Statue - 0.1 mi
- Ford Center for the Performing Arts Oriental Theatre - 0.2 mi
- Haskell Building - 0.2 mi
- Goodman Theater - 0.2 mi
- Chicago Cultural Center - 0.3 mi
- The Loop - 0.3 mi
- Children's Memorial Hospital - 0.3 mi
- Chicago Gospel Music Festival - 0.3 mi
- Millennium Park - 0.3 mi
- Chicago Theater - 0.3 mi
- Jay Pritzker Pavilion - 0.3 mi
- Chicago City Hall - 0.4 mi
- Theatre District - 0.4 mi
- Art Institute of Chicago - 0.5 mi
- Worth - 0.5 mi
- Symphony Center - 0.5 mi
- Monadnock Building - 0.6 mi
- Aon Center - 0.6 mi
- Fisher Building - 0.6 mi
- Magnificent Mile - Michigan Ave - 0.7 mi
- Old Colony Building - 0.7 mi
- Chicago Public Library (Harold Washington Library Center) - 0.7 mi
- Michigan Avenue Bridge - 0.7 mi
- Taste of Chicago - 0.7 mi
- Civic Opera House - 0.7 mi
- Fine Arts Building - 0.7 mi
- Merchandising Mart - 0.8 mi
- Wrigley Building - 0.8 mi
- Roosevelt University - 0.8 mi
- Willis Tower (formerly Sears) - 0.8 mi
- Chicago Blues Festival - 0.8 mi
- Auditorium Building and Theatre - 0.8 mi
- Tribune Tower - 0.9 mi
- Chicago Jazz Festival - 0.9 mi
- 311 South Wacker Parking - ParkChirp - 0.9 mi
- Lollapalooza - 1 mi
- Grant Park - 1 mi
- Union Station - 1 mi
- Buckingham Fountain - 1 mi
- Museum of Contemporary Photography - 1 mi
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Friendly staff, clean and close to the redline.
We have stayed at the Stay Pineapple six times and have loved it every time. It is a beautiful old bank building in downtown Chicago and is close the everything.
The room was clean, comfortable. The staff was friendly. Food and staff always excellent.
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Staypineapple An Iconic Hotel The Loop offers a unique and dog-friendly experience, accepting any number of pets without size or weight restrictions. They even have pet-free floors for guests with allergies.
We are sorry, but the requested room type has just sold out since your original search. It is rare that this happens, but it is possible if a certain room type is sold out or if the rate changes from the time you search to the time you attempt to book the reservation.
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We are sorry, but the requested room type has just sold out since your original search. It is rare that this happens, but it is possible if a certain room type is sold out or if the rate changes from the time you search to the time you attempt to book the reservation.
Please select another room type from the options below.
We are sorry, but the requested room type has just sold out since your original search. It is rare that this happens, but it is possible if a certain room type is sold out or if the rate changes from the time you search to the time you attempt to book the reservation.
Please select another room type from the options below.
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