Staypineapple, An Iconic Hotel, The Loop

Property class: 4

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Located close to Chicago Cultural Center and Chicago City Hall, Staypineapple, An Iconic Hotel, The Loop provides dry cleaning/laundry services and a gym.
VIP Access

Reviews

9.4 out of 10
Exceptional

Popular amenities

  • Air conditioning
  • Gym
  • Business services
  • Laundry

Room options

Available filters for rooms
Showing 10 of 10 rooms

View all photos for Burnham King

A hotel room with a large bed, a desk with a flat-screen TV, a bench, and a window with a city view.

Burnham King

9.4 out of 10
Exceptional
(23 reviews)
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed

View all photos for Atwood Queen

A hotel room with a large bed, a desk, a chair, a TV, and a window with curtains.

Atwood Queen

7.4 out of 10
Good
(13 reviews)
  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed

View all photos for Atwood Queen Mobility Accessible w/Tub

A hotel room with a large bed, a desk, a chair, a TV, and a window with curtains.

Atwood Queen Mobility Accessible w/Tub

  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed

View all photos for Atwood Queen Mobility Accessible w/Roll-in Shower

A hotel room with a large bed, a desk, a chair, a TV, and a window with curtains.

Atwood Queen Mobility Accessible w/Roll-in Shower

  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed

View all photos for Burnham Two Double Mobility Accessible w/Tub

A hotel room with two beds, a desk, a TV, and large windows with curtains.

Burnham Two Double Mobility Accessible w/Tub

10.0 out of 10
Exceptional
(3 reviews)
  • 1 bedroom
  • Sleeps 4
  • 2 Double Beds

View all photos for Burnham Two Double Mobility Accessible w/Roll-in Shower

A hotel room with two beds, a desk, a TV, and large windows with curtains.

Burnham Two Double Mobility Accessible w/Roll-in Shower

10.0 out of 10
Exceptional
(2 reviews)
  • 1 bedroom
  • Sleeps 4
  • 2 Double Beds

View all photos for Burnham 2 Two Queen

A hotel room with two beds, a TV, a desk, and a window with a city view.

Burnham 2 Two Queen

9.4 out of 10
Exceptional
(10 reviews)
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Reliance King Suite

A hotel room with a large bed, a TV on a wooden nightstand, a window with curtains, and a cityscape view.

Reliance King Suite

9.4 out of 10
Exceptional
(3 reviews)
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed

View all photos for Reliance King Suite Mobility Accessible w/Tub

A hotel room with a bed, a sofa, a desk, and a window with a city view.

Reliance King Suite Mobility Accessible w/Tub

9.4 out of 10
Exceptional
(3 reviews)
  • 1 bedroom
  • Sleeps 4
  • 1 Double Sofa Bed and 1 King Bed

View all photos for Millennium Park View King Suite

A hotel room with a large bed, a television, a window with curtains, a city view, and a painting on the wall.

Millennium Park View King Suite

10.0 out of 10
Exceptional
(2 reviews)
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed

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About the neighborhood

In the entertainment district, Staypineapple, An Iconic Hotel, The Loop is in Downtown Chicago, a walkable area in Chicago with good shopping. Art Institute of Chicago and Money Museum are cultural highlights, and some of the area's notable landmarks include Cloud Gate and Buckingham Fountain. Don't miss out on a visit to Chicago Cultural Center. Spend some time exploring the area's activities, including golfing. Guests appreciate the hotel's location for the sightseeing. Visit our Chicago travel guide
Map
1 W Washington St, Chicago, IL, 60602

What's nearby

  • A city street at night with illuminated buildings, a snow-covered sidewalk, and light trails from moving vehicles.
    Michigan Avenue
    3 min walk - 0.2 miles
  • A large metallic sphere sculpture in a public square surrounded by tall buildings.
    Millennium Park
    3 min walk - 0.2 miles
  • A cityscape at night with illuminated buildings, a river, and a bridge.
    Chicago Riverwalk
    5 min walk - 0.3 miles
  • A cityscape with a prominent modern sculpture in the foreground and a mix of historic and contemporary buildings in the background.
    Cloud Gate
    5 min walk - 0.3 miles
  • The Art Institute of Chicago building with classical architecture, a lion statue, and banners advertising events.
    Art Institute of Chicago
    6 min walk - 0.4 miles

Getting around

  • Washington Station
    1 min walk
  • Millennium Station
    5 min walk
  • Chicago Midway Airport (MDW)
    37 min drive

Restaurants

  • Magnolia Bakery
    1 min walk
  • Macy's Marketplace Grill
    3 min walk
  • The Dearborn
    3 min walk
  • Dunkin'
    3 min walk
  • Starbucks
    2 min walk

About this property

Staypineapple, An Iconic Hotel, The Loop

  • Upscale boutique hotel near Chicago Cultural Center
  • Located close to Chicago City Hall and Cloud Gate, Staypineapple, An Iconic Hotel, The Loop provides dry cleaning/laundry services and a gym.
  • You'll also find perks like:
    • Free bicycle rentals, valet parking (surcharge), and express check-out
    • A ballroom, free newspapers, and multilingual staff
    • 1 meeting room, a 24-hour front desk, and a porter/bellhop
    • Guest reviews speak highly of the dining options, helpful staff, and location
  • Room features
  • All 122 rooms include comforts such as premium bedding and laptop-compatible safes, as well as perks like air conditioning and bathrobes. Guest reviews speak positively of the clean rooms at the property.
  • More conveniences in all rooms include:
    • Hypo-allergenic bedding, pillowtop mattresses, and down comforters
    • Bathrooms with designer toiletries and shower/tub combinations
    • 50-inch LCD TVs with streaming services and premium channels
    • Recycling, free infant beds, and housekeeping

Awards and affiliations

  • Sustainability Certifications
  • This property is certified by this third-party sustainability certification scheme: Green Key Global. For more information on what this certification requires and verifies, please visit their website.

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Frequently asked questions

Is Staypineapple, An Iconic Hotel, The Loop pet-friendly?

Yes, dogs are allowed at this property. There's a fee of USD 29.95 per accommodation, per night. Service animals are exempt from fees.

How much does it cost to stay at Staypineapple, An Iconic Hotel, The Loop?

As of Oct 24, 2026, prices found for a 1-night stay for 2 adults at Staypineapple, An Iconic Hotel, The Loop on Nov 22, 2026 start from $227, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Valet parking is available for USD 75 per night.

What time is check-in at Staypineapple, An Iconic Hotel, The Loop?

Check-in start time: 4:00 PM; Check-in end time: midnight. After-hours check-in is not available.

What time is check-out at Staypineapple, An Iconic Hotel, The Loop?

Check-out is at noon.

Where is Staypineapple, An Iconic Hotel, The Loop located?

Located in Downtown Chicago, this boutique hotel is within a 10-minute walk of Chicago Cultural Center, Chicago City Hall, and Chicago Riverwalk. Cloud Gate and Art Institute of Chicago are also within 10 minutes. Washington Station is only a 2-minute walk and Lake Station is 3 minutes.

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on select room rates, because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

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Reviews

Staypineapple, An Iconic Hotel, The Loop Reviews

9.4

Exceptional

9.6

Cleanliness

8.8

Amenities

9.6

Staff & service

9.4

Property conditions & facilities
Rating 10 - Excellent. 900 out of 1189 reviews
Rating 8 - Good. 191 out of 1189 reviews
Rating 6 - Okay. 59 out of 1189 reviews
Rating 4 - Poor. 19 out of 1189 reviews
Rating 2 - Terrible. 20 out of 1189 reviews

Reviews

Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very comfortable beds and friendly, helpful staff.
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff were welcoming and helpful. The location was great. We had a great view from our room. The beds were very comfortable too. We did not eat at the restaurant/bar but it was a nice ambiance for those who did.
Stayed 2 nights in Oct 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice place in a great location,
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful architecture and aesthetics. On site restaurant is superb, above par. Fabulous place.
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Such a cute hotel. Great downtown views. Stylish cutie
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
StayPinapple Chicago is a really beautiful restored hotel just off of Michigan Ave. You have old fashioned turn key doors and a small, but very functional hotel room. The split duvet was a nice touch. The bed was comfortable, and the bathroom had an endless supply of hot water. The restaurant downstairs was nice, but a bit over the top for my taste, however breakfast was really good, and their coffee was excellent.
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location for Lollapalooza, lots of character (in a good way). Loved the keys and super heavy doors. Nice stay.
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fantastic reno of a beautiful Art Deco historical building. One of the most comfortable hotels I’ve stayed at. Love the lobby bar and restaurant which has a fantastic happy hour! Highly recommend and will make a point of staying again.
Stayed 1 night in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, property conditions & facilities
Disliked: Amenities
It was nice and in the perfect location.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location and easy public transportation to explore the city and Wrigley field. Lovely room with great view.
Stayed 4 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Good hotel with a great location, make sure you do not get a room in the light well if the building.
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everyone was very welcoming. Great spot, close to everything. The restaurant downstairs had excellent coffee and staff. We were very thankful for valet service. Again, great location. Loved the whole theme of the place.
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Right next to The Loop and Millennium Park; great location.
Stayed 2 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Good location, friendly staff
Stayed 5 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property was in a wonderful area where you could easily walk to any attractions without having to find an Uber. The staff were extremely kind and helpful! I recommend for anyone visiting Chicago who wants everything in walking distance!
Stayed 2 nights in Aug 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Room was clean but maybe needs a little TLC, especially a new bed. Otherwise the stay was great!! Drinks were great, staff was great, and close to tourist things.
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Always very nice, great location and building
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Absolutely spectacular hotel- loved the real key locks, soap dispensers instead of wasted plastic, and water fillers. Incredible views from the room too!
Stayed 1 night in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was very helpful with wayfinding and suggestions for activities
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We really appreciated the baby-friendly amenities, well lit room, and comfortable bed. We will definitely stay again.
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The room was spacious for Chicago & the bed was very comfortable. The staff was very friendly and accommodating. I would definitely stay here again.
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Fantastic place to stay, especially if you are looking to walk around the city. Super convenient location and amazing accommodations. The staff were super helpful and valet parking made getting in and out super easy.
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Such a lovely hotel with a beautiful, excellent staff, and lots of character!
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great staff! Hosted at restaurants was excellent ‘!
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities
Really nice historic hotel. Love the old school touches (physical key for room!). Really friendly and welcoming staff. Great location. Nice comfortable room. Gym was a bit on the small side.
Stayed 5 nights in Jul 2026