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Staypineapple, An Iconic Hotel, The Loop

1 W Washington St | Chicago, IL 60602-1603  [SEE MAP]Chicago, IL  [SEE ADDRESS]

Courtesy of Staypineapple, An Iconic Hotel, The Loop

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Located in the iconic Reliance Building
Smaller rooms than comparable hotels
Occupying a National Historic Landmark building in the Loop, Staypineapple Chicago is lauded by recent visitors for its historic ambiance and convenient Chicago location. Tucked in the Reliance Building (an old office skyscraper built in 1895), Staypineapple Chicago channels its ornamental decor with features like mahogany office doors, terrazzo tile floors and white marble wainscoting. The distinct style carries into the rooms, which are dressed in gold and navy hues but come outfitted with contemporary amenities like flat-screen TVs and honor bars. Although they love the look of the Staypineapple Chicago's accommodations, some travelers warn that the rooms – originally built as office spaces – are a bit cramped. Still, visitors say that a stay here is worth sacrificing a few square feet. The Staypineapple Chicago houses a fitness center and American restaurant, Atwood. Plus, it offers numerous signature amenities, including a pet-friendly atmosphere, robes and slippers and yellow beach cruisers to use around the city.
Chicago, IL
Hotel Class
Property Type
Boutique hotel, 122 rooms
Primary View
City center



  • 4.0Hotel Class
  • GOODCritic Rating


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Critic Reviews

Other Awards

  • Frommer's Very Highly Recommended


This 122-room boutique located in an 1895 building pays homage to its past with cool historic details, including wrought iron, mosaic tiles, and marble stairs.

The Telegraph


Vintage details inside include iron filigree stairwell railings, flowery Deco-style ceiling lights, Italian marble walls and mosaic-tile floors. A sense of historic cool pervades throughout.

Other Awards

  • Frommer's Very Highly Recommended

Guest Reviews

A hotel's guest rating is calculated using data provided under license by Tripadvisor. A total of 2736 have reviewed the Staypineapple, An Iconic Hotel, The Loop, giving it a rating of 4.5, on a scale of 1-5.

Tripadvisor Travel Rating: 

Tripadvisor Travel Rating: Tripadvisor Traveler Rating 4.5 based on 2736 reviews 4.5 (based on 2736 reviews)

Guest Rooms

A National Historic Landmark building houses the Staypineapple hotel, and many of the accommodations still carry original touches from one of the oldest skyscrapers in America. Rooms and suites come decorated with white walls, grey fabrics, and dark wooden furniture and floors. The property isn't stuck in the past though, and guests can expect modern amenities ranging from flat-screen TVs to complimentary Wi-Fi access. Visitors will also find an abundance of pineapples, the hotel chain's signature touch, around their rooms. In-room Wi-Fi is complimentary on unlimited devices.
  • $15 per night amenity fee added to all room rates

Standard room size175 square feet

  • Premium channels
  • Workspace/desk
  • Minifridge
  • Bathrobes/slippers
  • Minibar
  • Shower/tub combo
  • Separate shower
  • Separate tub
  • Internet
  • Wireless internet
  • Free internet
  • Fee for internet usage
  • Guest rooms with patios and balconies
  • Adjoining rooms available

Location & Parking

Situated in the Loop area of Chicago, Staypineapple is centrally located near many of the city's top tourist destinations. Millennium Park is just two blocks east and the Chicago Theatre is two blocks north of the property.
  • Self-parking is available at nearby unaffiliated parking lots
  • Walking distance to multiple L train stations and bus stops
  • Navy Pier and Ohio Street Beach located less than 2 miles away
  • 24-hour valet parking ($62)
  • 24-hour self-parking
  • Airport shuttle
  • Car service

Within walking distance of:

  • Bus stop
  • Restaurants
  • Movie theater
  • Train station
  • Beach
  • Theater
  • Subway/metro stop
  • Grocery store
  • Shopping


The Atwood restaurant at Staypineapple Chicago serves American comfort food dishes made from fresh, seasonal ingredients. Private dining is available, and room service is offered 24 hours a day.
  • Breakfast available Monday to Friday from 7 to 10:30 a.m. and lunch available Monday to Friday from 11:30 a.m. to 2:30 p.m.
  • Brunch available Saturday and Sunday from 8 a.m. to 2:30 p.m.
  • Dinner available from 4:45 to 9 p.m. Sunday through Thursday and 10 p.m. Friday and Saturday

Number of restaurants1

Cuisine TypesAmerican

  • Fine dining
  • Casual dining
  • Quick service cafe/coffee shop/marketplace
  • Bar/lounge
  • Room service
  • 24-hour room service
  • free breakfast


The Staypineapple Chicago has an on-site fitness center that is open 24 hours a day. The fitness center features cardio equipment, medicine balls and weight-training machines.
  • Guests can borrow bikes and helmets and locks to explore Chicago
  • Weight equipment
  • Cardio equipment
  • Yoga mats
  • Free fitness classes
  • Premium fitness classes (with fee)


The property offers space in which to host business meetings for up to 40 guests in The Burnham Room.
  • Business center is accessible 24 hours a day
  • Catering provided by Atwood restaurant
  • Business center
  • Meeting rooms
  • Meeting and event planners available


The Staypineapple Chicago welcomes up to two dogs, with no weight or breed restrictions. Pets are welcomed with a goodie bag that includes a dog bed, water bowl, tasty treats and a baggie dispenser with bags.
  • $25 daily pet fee applies
  • Pet-sitting and dog-walking services from outside providers can be recommended by hotel staff
  • Pets allowed (free)
  • Dog walking (with fee)
  • Pet-sitting (with fee)


Space for wedding ceremonies is limited at Staypinapple Chicago, but guests are welcome to host small events in The Burnham Room. This room can accommodate up to 28 guests for a seated dinner, or 50 guests for a cocktail reception.
  • Catering available through Atwood restaurant

Maximum wedding guest capacity50

  • Hotel hosts weddings
  • Outdoor space for weddings
  • Wedding planners available

Editor’s note: Hotel information is updated periodically. If this is your property and you notice any inaccuracies, please let us know.

Find the Best Price

at the Staypineapple, An Iconic Hotel, The Loop

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