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Staypineapple, An Iconic Hotel, The Loop Chicago

1 W Washington St, Chicago, IL 60602-1603
COVID-19 update: See the added health and safety measures this property is taking.Read more
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Traveler (862)
Panoramas (32)
Room & Suite (539)
What is Travelers’ Choice?
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Travel safe during COVID-19
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What you can expect during your stay
  • Face masks required for guests in public areas
  • Face masks required for staff in public areas
  • Floors marked for social distancing
  • Hand sanitizer available to guests & staff
  • Regularly sanitized high-traffic areas
  • Staff required to regularly wash hands
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Updated 06/24/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.
A note from Staypineapple, An Iconic Hotel, The Loop Chicago
Updated 06/24/20 Safety precautions are provided by the property and are not checked by Tripadvisor for accuracy.


#33 of 215 hotels in Chicago
Travelers' Choice
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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Full view
Property amenities
Valet parking
Free High Speed Internet (WiFi)
Fitness Center with Gym / Workout Room
Bicycle rental
Pets Allowed ( Dog / Pet Friendly )
Business Center with Internet Access
Meeting rooms
Baggage storage
Paid private parking on-site
Paid wifi
Non-smoking hotel
ATM on site
24-hour front desk
Express check-in / check-out
Dry cleaning
Laundry service
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Room features
Allergy-free room
Air conditioning
Room service
Bottled water
Flatscreen TV
Hair dryer
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Room types
Non-smoking rooms
Good to know
Historic Hotel
Languages Spoken
2844Reviews38Q+A100Room tips
Traveler rating
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Popular mentions
Tour79219 wrote a review Today
6 contributions1 helpful vote
Has some flaws but would probably stay here again in a pinch Pros: -AMAZING location. Straight shot on the blue line from O'Hare with minimal walking. Very close to restaurants, shopping and public transportation. - Dark, Quiet, spacious rooms -Friendly Staff -Price Cons: -Not the cleanest hotel room. Towels had stains and there was some mold in the tub. -Bed only has a heavy down comforter with no top sheet. It made for a a night of being sweating then cold. -Pretty soft mattress which led to some back pain. However, I fully acknowledge this is a personal preference and may not bother some people.
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Date of stay: June 2021Trip type: Traveled as a couple
Geeena wrote a review Jun 9
San Francisco, California322 contributions79 helpful votes
We arrived at the same time as a few others so it was little hectic at front desk but staff was friendly and nice. Be aware $15 resort fee is charged but you get $10 in credit back for some drinks and snacks available in lobby plus Keurig coffee in room and bottled water. You have to ask about pineapple cookies I did not get any until I was leaving and only because the person checking in as I was checking out asked for them! The beds were great, towels were okay, bathrobes were a nice touch and we had a nice view of the city with tall corner windows. Our room had 2 queen very comfortable beds. The room itself was not spacious but not too crowded. We loved the style of this place and it is ideally located. We got off red line, exiting via escalator in the mall and were practically at front door of hotel. Leaving was just as easy through the same mall to the blue line. The price for this place was very reasonable for Chicago. I highly recommend it and would stay here again if I come back.
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Date of stay: June 2021
flamingogurl wrote a review May 2021
Louisiana20 contributions25 helpful votes
What an awesome hotel!! We loved everything about Staypineapple Chicago. I always look for unique hotels, and this one did not disappoint. In fact, it exceeded our expectations. Staff is super awesome with friendly greetings whenever we walked by. The “real” room key is a rarity & we loved that unique feature of this iconic hotel. Also, this hotel has the most beautiful staircase. (Actually, the word “hotel” just doesn’t seem good enough for this place.) It was really fun selecting our daily snack bar goodies! Just an added bonus that helped make this hotel one of the best we’ve ever stayed in. And the staff was always very accommodating with our snack bar selections, super friendly and always willing to pop over to help us right away. The Keurig coffee maker was so nice to have in the room, and the Staypineapple branded K-cups were really great! We’re kind of coffee snobs LOL but these medium roast cups are nice & robust and very satisfying. Liquid creamer and bottled water are also very appreciated amenities. The pineapple charging station is so convenient. Robes, bedding & towels are over-the-top soft. Kudos to the friendly & personable housekeeping staff - the room was immaculately clean from the beginning to the end of our stay. Water pressure in the shower was nice & strong, and we always had very hot water. Soap, shampoo, conditioner & lotion dispensers are filled with lovely scented Tommy Bahama products. I can’t state enough good points about Staypineapple Chicago. It was a wonderful place to stay while visiting Chicago and made our first visit to the city very memorable. It’s an extremely convenient location with so many sights & bars & restaurants in very close proximity. We were non-stop, so we didn’t get a chance to use the bikes, but maybe next time. Thanks to Cole, the head pineapple, who is obviously doing an amazing job making this one super special destination. Can’t wait to visit again :)
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Date of stay: May 2021Trip type: Traveled as a couple
Response from Cole Mansfield, General Manager at Staypineapple, An Iconic Hotel, The Loop Chicago
Responded 2 weeks ago
Thank you for the awesome review! We are so happy you enjoyed your stay and can’t wait to see you again. Let me know next time you are here or at any of our other Staypineapple locations, so we can do a little something extra for you! We appreciate you!
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CINDYROSE720 wrote a review May 2021
Denver, Colorado936 contributions213 helpful votes
2021-May: I arrived to this hotel at around 11am on a Saturday. Came through a double door towards the front desk. Staff was pleasant and professional. Our room was not ready but they were able to store and lock our luggage. The hotel has regular bicycles for customers. Elevators were... ummm... nostalgic?lol. But works efficiently. The room key is an actual key with a keychain, lol. The room was clean. Small, but decent. A bed, a night stand in one side, a desk on the other side. Lamp on each side. Two chairs, mini fridge, coffee maker, full size mirror. Desk has usb and outlet plugs. Bed is comfortable. 2 comforters were on top of the bed. Bathroom was clean. Lots of counter space around the single-sink in the bathroom. 4 bath towels, 2 hand towels, 2 face towels, and a hair dryer were available. Hotel toiletries were installed permanently on the walls of the bathroom. Shower has decent pressure. TV has HDMI hookups for my fire stick. 2 complimentary water bottles were provided. The facility requires everyone wears masks outside their room. There was no pool. If you think this review helped you in any way, please give it a thumbs up! Hope you have a great vacation!
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Date of stay: May 2021Trip type: Traveled as a couple
1 Helpful vote
Olivia B wrote a review May 2021
7 contributions
This was the coolest hotel I've ever stayed at! The history is so well preserved and beautiful, down to the doorknobs. You will get an actual key for a lock rather than a scanned card because even the doors are historic. The amenities were fantastic, especially the $10 credit for snacks each day. The staff were all extremely friendly and helpful. The hotel's location is perfect, too! You're about an equal distance from the Field museum/Aquarium on one side and stores like the American Girl Doll Place to the other. You're also less than a half mile from the water! It is RIGHT next to an L-train too. If you take the blue lune from the airport, you get off pretty much right at the hotel. The rooms were clean, the views were incredible, and the building is gorgeous. Highly Recommend!
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Date of stay: April 2021
Sleep Quality
Room Tip: Floor 15 is the highest. All rooms have a great city view!
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Response from Cole Mansfield, General Manager at Staypineapple, An Iconic Hotel, The Loop Chicago
Responded 2 weeks ago
Wow, we are almost blushing over your review! Awesome. We appreciate the kudos and are so happy you stayed with us. Come back again and let me know when you do, so we can do a little pineapple something extra for your next stay.
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$149 - $422 (Based on Average Rates for a Standard Room)
hotel burnham kimpton, hotel burnham chicago
Hotel Burnham
United StatesIllinoisChicagoCentral / Downtown / The Loop / Theater District
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Frequently Asked Questions about Staypineapple, An Iconic Hotel, The Loop Chicago
Which popular attractions are close to Staypineapple, An Iconic Hotel, The Loop Chicago?
Nearby attractions include Millennium Park (0.3 miles), Cloud Gate (0.3 miles), and The Magic Parlour (0.2 miles).
What are some of the property amenities at Staypineapple, An Iconic Hotel, The Loop Chicago?
Some of the more popular amenities offered include free wifi, a fitness center, and room service.
Is parking available at Staypineapple, An Iconic Hotel, The Loop Chicago?
Yes, paid private parking on-site, secured parking, and valet parking are available to guests.
What are some restaurants close to Staypineapple, An Iconic Hotel, The Loop Chicago?
Conveniently located restaurants include Wildberry Pancakes and Cafe, Do-Rite Donuts & Chicken, and Cherry Circle Room.
Are there opportunities to exercise at Staypineapple, An Iconic Hotel, The Loop Chicago?
Yes, guests have access to a fitness center during their stay.
Is Staypineapple, An Iconic Hotel, The Loop Chicago located near the city center?
Yes, it is 0.3 miles away from the center of Chicago.
Are any cleaning services offered at Staypineapple, An Iconic Hotel, The Loop Chicago?
Yes, dry cleaning and laundry service are offered to guests.
Are pets allowed at Staypineapple, An Iconic Hotel, The Loop Chicago?
Yes, pets are typically allowed, but it's always best to call ahead to confirm.
Does Staypineapple, An Iconic Hotel, The Loop Chicago offer any business services?
Yes, guests have access to a business center and meeting rooms during their stay.
Are there any historical sites close to Staypineapple, An Iconic Hotel, The Loop Chicago?
Many travelers enjoy visiting Garfield Park Conservatory (4.6 miles), The Rookery Building (0.3 miles), and Macy's on State Street (0.09 miles).
Is Staypineapple, An Iconic Hotel, The Loop Chicago accessible?
Yes, it offers wheelchair access, reduced mobility rooms, and facilities for disabled guests. For specific inquiries, we recommend calling ahead to confirm.