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Staypineapple, An Iconic Hotel, The Loop

Property class: 4

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Photo gallery for Staypineapple, An Iconic Hotel, The Loop

A corridor with ornate black metal railings and a patterned carpet. - Staypineapple, An Iconic Hotel, The Loop (Chicago)
A bed with a pillow featuring a pineapple design and the text "Sleep with me." A window reveals a cityscape at night. - Staypineapple, An Iconic Hotel, The Loop (Chicago)
A modern hotel room with a sofa, a small table, a bench, a TV, and a cabinet. - Staypineapple, An Iconic Hotel, The Loop (Chicago)
A multi-story building with a grid of windows, surrounded by other high-rise buildings. - Staypineapple, An Iconic Hotel, The Loop (Chicago)
A dining area with tables and chairs, a hanging light fixture, and a view of the street through a window. - Staypineapple, An Iconic Hotel, The Loop (Chicago)
Located close to Chicago Cultural Center and Chicago City Hall, Staypineapple, An Iconic Hotel, The Loop provides dry cleaning/laundry services and a gym.

Reviews

9.4 out of 10
Exceptional

Popular amenities

  • Air conditioning
  • Gym
  • Parking available
  • Business services
  • Laundry

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Skip the crowds, keep the savings. AARP members save more after Labor Day. Book by Oct 7, 2026.

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

7.2 out of 10
Good
(12 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

About the neighborhood

Located near the beach, 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 grand hall with a high, ornate ceiling and intricate architectural details.
    Chicago Cultural Center
    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
  • A grand staircase in a historic building with classical architecture, including columns and ornate railings.
    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
  • Starbucks
    2 min walk
  • Petterinos
    3 min walk

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Property amenities

Internet

  • Available in all rooms: Internet access (surcharge)

Parking and transportation

  • Valet parking on site (USD 75 per night)

Food and drink

  • Coffee and tea in common areas

Things to do

  • Free bicycle rentals
  • Gym

Family friendly

  • In-room crib

Conveniences

  • 24-hour front desk
  • Free newspapers in lobby
  • Luggage storage
  • Safe at front desk
  • Water dispenser

Guest services

  • Dry cleaning/laundry service
  • Housekeeping (on request)
  • Multilingual staff
  • Porter/bellhop
  • Tour and ticket assistance
  • Turndown service

Business services

  • Meeting room

Accessibility

  • No elevator

More

  • 15 floors
  • Ballroom
  • Banquet hall
  • Built in 1895
  • No plastic water bottles
  • Smoking not allowed
  • Water dispenser usage encouraged

Room amenities

Bedroom

  • Down comforter
  • Free crib
  • Hypo-allergenic bedding
  • Pillowtop mattress
  • Premium bedding

Bathroom

  • Bathrobes
  • Designer toiletries
  • Hair dryer
  • Private bathroom
  • Shower/bathtub combination
  • Towels provided

Entertainment

  • 50-inch LCD TV with premium cable channels
  • iPod dock
  • Streaming services

More

  • Air conditioning (climate-controlled)
  • Connecting rooms available
  • Desk
  • Free daily newspapers
  • Iron/ironing board
  • Laptop-compatible safe
  • Phone

Policies

Check-in

Check-in start time: 4:00 PM; Check-in end time: midnight
Minimum check-in age: 18

Check-out

Check-out before noon
Contactless check-out available
Express check-out available

Special check-in instructions

Front desk staff will greet guests on arrival at the property
This property doesn't offer after-hours check-in
Information provided by the property may be translated using automated translation tools

Access methods

Staffed front desk

Pets

Pets allowed for an extra charge of USD 29.95 per accommodation, per night
Service animals are welcome, and are exempt from fees
Welcoming dogs only
Food and water bowls are available

Children and extra beds

Children are welcome
Rollaway/extra beds are not available
Free cribs are available on request at the property

Property payment types

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • Resort fee: USD 29.66 per accommodation, per night
The resort fee includes:
  • Fitness center access
  • In-room bottled water
  • In-room coffee
  • In-room safe
  • Internet access
  • Sporting facilities or equipment

We have included all charges provided to us by the property.

Optional extras

  • Valet parking fee: USD 75 per night
  • Pet fee: USD 29.95 per accommodation, per night
  • Service animals are exempt from fees

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Special cancellation policies or charges may apply for group reservations (more than 8 rooms for the same property / stay dates)
This property accepts credit cards; cash is not accepted
Cashless transactions are available
Safety features at this property include a fire extinguisher and a smoke detector

We should mention

This property does not have elevators
Only registered guests are allowed in the guestrooms
The property has connecting/adjoining rooms, which are subject to availability and can be requested by contacting the property using the number on the booking confirmation
This property welcomes guests of all sexual orientations and gender identities (LGBTQ+ friendly)

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 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. 898 out of 1184 reviews
Rating 8 - Good. 190 out of 1184 reviews
Rating 6 - Okay. 57 out of 1184 reviews
Rating 4 - Poor. 19 out of 1184 reviews
Rating 2 - Terrible. 20 out of 1184 reviews

Reviews

Verified review

8/10 Good

Jennifer

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

Nathan

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

Caroline

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

Teresa

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

Melissa

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

Beth

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

10/10 Excellent

Chelsea

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

SHAWN

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

Joshua

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

Philip

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

10/10 Excellent

Amy

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

Debby

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

Anna

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This hotel really is iconic. It offers a prime location in a great section of downtown, less than a block from the Blue Line train and within walking distance of Michigan Avenue. The aesthetic is classy, from the lobby and restaurant to the elevators to the rooms; everything looks chic and arty. We especially enjoyed the daily cookie, the refillable water bottle in the room, and all the pineapple-themed decor. Every time we encountered any staff, they were friendly and accommodating. The stay here really made our Chicago trip amazing; I highly recommend Staypineapple and will definitely return!
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Michael

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

Ashley

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Really lovely historic space close to transit and many sights in downtown Chicago! The staff were excellent and kind. Bed was very comfortable. Nice amenities like coffee in the afternoons and breakfast in the morning. Very close to L trains and walkable to lots of great architectural sights (go across the street to the Macy’s and see the interior Tiffany mosaic atrium, you won’t be disappointed). A great spot for solo travel as well! Thanks to everyone who made my stay cozy.
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

George

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Usually, I have difficulty falling asleep on the first night. Enjoyed the bed, slept well every night, very comfortable. Rooms were clean and had a good view of the city. Also, easy access to River Walk and Millennium Park.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Christine

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great location, rustic but feeling super clean, comfortable bed, great city view, walking distance to the millennium park and pretty much everywhere. Helpful and friendly staffs. Definitely will come back!
Stayed 5 nights in Jun 2026
Verified review

8/10 Good

Leslie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice hotel, fun, great location! I do wish there were places to refill your water bottles on each floor, but I love that hotels are starting to do this.
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful restaurant, amazing food.
Stayed 1 night in Jan 2026
Verified review

10/10 Excellent

Marlena

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great spot in the city with convenient valet parking. Big, clean rooms with tall ceilings. Comfy beds and great water pressure. Would definitely stay again. Dog and baby friendly
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

Tammy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful hotel. Great location at a great price.
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Lisa

Liked: Cleanliness, staff & service, property conditions & facilities
Great location with excellent beds
Stayed 1 night in Mar 2026
Verified review

10/10 Excellent

Carrie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Location is perfect!!! Directly adjacent to bus and train. Held our bags both before check in and after checkout. The hotel and rooms are quirky and fun, everything was very comfortable and we enjoyed it. The breakfast restaurant (not included) was spectacular!!!
Stayed 1 night in Jun 2026
Verified review

8/10 Good

Analicia

Liked: Cleanliness, staff & service
Lots of places to eat and shop nearby
Stayed 1 night in Mar 2026
Verified review

10/10 Excellent

Jeremy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff is super friendly and easy to talk to so you don’t have to worry about much! The location is amazing if you wanna explore downtown Chicago!
Stayed 3 nights in May 2026