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Staypineapple, An Iconic Hotel, The Loop Chicago

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Traveller (779)
Panoramas (32)
Certificate of Excellence


Certificate of Excellence
GreenLeaders Gold level
Chosen by Conde Nast Traveler as one of the best hotels in the world, Staypineapple Chicago is an intimate boutique hotel like no other. Housed in the landmark Reliance Building, now beautifully restored, Staypineapple Chicago provides an authentic, luxurious and historic taste of the Windy City. In the heart of the Chicago Loop, across from Millennium Park, and home of the Atwood Restaurant, Staypineapple is near Chicago's top destinations and attractions. See the Windy City with the perfect homebase: Staypineapple, An Iconic Hotel, The Loop Chicago
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Property amenities
Room Service
Fitness Centre with Gym / Workout Room
Free High Speed Internet (WiFi)
Business Centre with Internet Access
Conference Facilities
Dry Cleaning
Laundry Service
Meeting Rooms
Multilingual Staff
Non-Smoking Hotel
Paid Internet
Paid Wifi
Pets Allowed ( Dog / Pet Friendly )
Wheelchair access
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Room features
Air Conditioning
Non-Smoking Rooms
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Hotel links
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Full view
100Great for walkers
Grade: 100 out of 100
355Restaurantswithin 0.3 miles
73Attractionswithin 0.3 miles
Downtown / The Loop
Often visitors' first stop in Chicago, The Loop is a good starting point to sample the city's energy and flavor. This central business district boasts Michelin-rated restaurants, upscale hotels, premier shopping, and enough arresting architecture to keep your camera busy for hours. You won’t find too many photo galleries of downtown Chicago without a shot of Millennium Park and Cloud Gate (“The Bean”), one of the most iconic landmarks in the city. A stunning skyline coupled with cultural attractions like the Art Institute of Chicago present a Downtown where work and play peacefully coexist.
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100Room tips
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Popular mentions
Amazing location, staff is so helpful and friendly. Great views and unique ambience inside. My room had a beautiful view of the Chicago theater. Can’t beat the price! Food and drinks are great as well.
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Review collected in partnership with this hotel
Hotel's Favourite
The hotel was beautiful, clean. Front desk always friendly and helpful. Best place I have stayed in Chicago. Amazing views from the windows of the hotel. Definitely a gem in Chicago in a beautiful neighborhood
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Review collected in partnership with this hotel
Response from AbbyG450, Front Office Manager at Staypineapple, An Iconic Hotel, The Loop Chicago
Responded 5 Dec 2018
Dear HeatNew, You are a gem for leaving us those nice comments! Our rooms have been set up to provide our guests postcard perfect views from almost every window and I am so glad you enjoyed. The front desk has a passion for helping people, and I am delighted to hear they made you feel welcome. We can't wait to host you again soon!
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Love the beds and bedding Staff is very accommodating and rooms are very clean. Also like having water and Kurig coffee. Such a great location. Right by Nacys State street and many great restaurants including the Atwood’s
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Review collected in partnership with this hotel
We had a fantastic stay! Everyone was very nice and helpful. We were given the wrong room initially, but after a call to the front desk, a bellman quickly came and brought our things to the correct room. We stayed in the Millennium Park View King Suite, which was perfect for
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Response from TabithaL144, Supervisor at Staypineapple, An Iconic Hotel, The Loop Chicago
Responded yesterday
Dear mvsap, Wow five stars, Awwww Thank you, for this fantastic review! We are so glad that you found all of our hotel staff friendly, helpful and quick service for your stay. Yes, our famous millennium park view king suite is to die for, accommodating with enough space for a family of 5 and with a great view to add extra pineapple happiness!. Our location is tooo perfect to talk about! We love the exact description you gave mvsap with all the greatness surrounding us. As you mention Block 37 with has movies theaters , shopping areas( indoor/outdoor and a bakery. Wild berry which is a high servicing of yummy breakfast foods. And who can forget the Cloud gate, so enjoying. We look forward to seeing you the next time you all visit Chicago! Best regards,
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My boyfriend booked this hotel for us to celebrate after our engagement in downtown Chicago. This hotel's pineapple theme with a dog mascot makes it so fun and eclectic. This hotel is also historic with their old style room keys and marble features. A perfect mix of historic and
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Review collected in partnership with this hotel
Response from TabithaL144, Supervisor at Staypineapple, An Iconic Hotel, The Loop Chicago
Responded 3 days ago
Dear Maps18138173495, Thank you for the wonderful review! We are so happy you found our amazing staff(Lindsay and Devon) very friendly helpful and perfect models of employee during your stay. Congrats on your engagement. We look forward to seeing you and celebrating every occasion with you. We are glad that out staff made you special day that much sweeter. Look forward to seeing you all soon! Best regards,
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Professional photo exclusively commissioned by TripAdvisorStaypineapple, An Iconic Hotel, The Loop Chicago
The Queen Room at The Staypineapple, An Iconic Hotel, The Loop
Professional photo exclusively commissioned by TripAdvisorStaypineapple, An Iconic Hotel, The Loop Chicago
The King Room at The Staypineapple, An Iconic Hotel, The Loop
Hello ramayo66, A taxi or rideshare can be anywhere from $35 to $60 depending on when you are traveling. We always recommend taking the CTA Blue Line subway. It begins at the O'hare Airport and takes about 45 minutes the Washington Street stop, where you are about 100 yards from our front door! The subway ticket is $3.00 one way. I hope this answers your question!
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Mine did not (that I was aware of). I know you can get they can provide a cot per request
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Union Station is about a $7 cab ride to the hotel. Luggage is pretty easy to deal with by taxi or Uber. I'd feel uncomfortable using the bus or other transportation to get to either airport. I've heard it is about a $45 cab ride from O'Hare to downtown.
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Thank you for asking Kay! Yes! You can keep Dash, our mascot. He is $25+tax and when he is purchased all proceeds go to the local no-kill shelter PAWS Chicago! Abby G. Front Office Manager
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"Floors in bathroom are marble so can be chilly-take advantage of the free slippers from front desk if your forget yours!"
"The suite we stayed in was at the end of the hall and was quiet."
"Corner rooms, suites are the best!"
"You won't want to get out of bed!"
"The eight floor and up are great views."
US$131 - US$483 (Based on Average Rates for a Standard Room)
hotel burnham kimptonhotel burnham chicago
Hotel Burnham
United StatesIllinoisChicagoCentralDowntown / The LoopTheater District
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