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Staypineapple, An Iconic Hotel, The Loop

4.0 star property

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Meeting facility - Staypineapple, An Iconic Hotel, The Loop (Chicago)
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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.

Reviews

9.4 out of 10
Exceptional

Popular amenities

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

Room options

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Showing 10 of 10 rooms

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Burnham King

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

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Atwood Queen

7.8 out of 10
Good
(9 reviews)
  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed

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Atwood Queen Mobility Accessible w/Tub

  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed

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Atwood Queen Mobility Accessible w/Roll-in Shower

  • 1 bedroom
  • Sleeps 3
  • 1 Queen Bed

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Burnham Two Double Mobility Accessible w/Tub

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

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Burnham Two Double Mobility Accessible w/Roll-in Shower

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

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Burnham 2 Two Queen

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

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Reliance King Suite

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

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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

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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

  • Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept
    Michigan Avenue
    3 min walk - 0.2 miles
  • Reflection of a Chicago buildings in a mirror of Chicago Bean, Millennium Park, Chicago city, USA., Shutterstock ID 1129809965, Purchase Order: SP-2109, Order Number: SP-2109 Qantas AU US Sale New Ads
    Millennium Park
    3 min walk - 0.2 miles
  • Chicago, United States - November 3, 2019: Cloud Gate, a public sculpture at Millennium Park in the Loop community area of Chicago
    Cloud Gate
    5 min walk - 0.3 miles
  • Chicago Riverwalk
    Chicago Riverwalk
    6 min walk - 0.4 miles
  • Art Institute of Chicago
    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
  • The Walnut Room
    1 min walk
  • Starbucks
    2 min walk
  • Garrett Popcorn Shops
    2 min walk
  • Chipotle Mexican Grill
    2 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 Cloud Gate. Chicago Riverwalk 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. 845 out of 1103 reviews
Rating 8 - Good. 166 out of 1103 reviews
Rating 6 - Okay. 56 out of 1103 reviews
Rating 4 - Poor. 17 out of 1103 reviews
Rating 2 - Terrible. 19 out of 1103 reviews

Reviews

Verified

8/10 Good

Philip

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

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

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

10/10 Excellent

Robert

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

10/10 Excellent

Jessica

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Darnell at the front desk was so warm and helpful. Our room was as pretty and cozy as it gets, the view to die for. The restaurant downstairs has the best French toast on earth. For reals!
Stayed 1 night in Jun 2026
Verified

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
Verified

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

8/10 Good

Analicia

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

10/10 Excellent

Diane

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Convenient location, walked everywhere. Great staff, so helpful amd accommodating.
Stayed 1 night in Apr 2026
Verified

10/10 Excellent

Barbara

Liked: Cleanliness, staff & service, amenities
Amazing hotel and amazing staff.
Regular King room
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Irasema

Liked: Cleanliness, amenities, property conditions & facilities
Great location
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Julie

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great property, so many cute details in this historic hotel. The staff was friendly, the property was pristine, and it’s close to so many things to visit and do in Chicago. A close walk to Millennium Park, and many shops.
Stayed 1 night in Mar 2026
Verified

10/10 Excellent

Joseph

Liked: Cleanliness, staff & service, property conditions & facilities
Close to shops, theater and restaurants.
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Jolyn

Liked: Cleanliness, staff & service, amenities
Everything was great, including the staff
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Timothy

Liked: Cleanliness, staff & service, amenities
The whole ambience of the hotel, room was very clean, staff was very friendly.
Stayed 1 night in Feb 2026
Verified

10/10 Excellent

Lou Ann

Liked: Cleanliness, staff & service, amenities
Great staff and the location was perfect.
Stayed 2 nights in Nov 2025
Verified

10/10 Excellent

Philip

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Center of the Loop, easy walk to a majority of landmark sights.
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Lori

Liked: Cleanliness, amenities, property conditions & facilities
Location was great, staff was very friendly, and the rooms were clean.
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Kathleen

Liked: Cleanliness, amenities, property conditions & facilities
Great hotel location and friendly staff!
Stayed 1 night in Dec 2025
Verified

10/10 Excellent

Robin

Liked: Cleanliness, staff & service, amenities
Very friendly and attentive staff. The bedding is super comfortable.
Stayed 1 night in Nov 2025
Verified

10/10 Excellent

Samantha

Liked: Cleanliness, staff & service, amenities
The staff was amazing and even sent a bottle of wine with a hand written card! The room was clean and comfortable and I was happy with how close everything was!
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Jennifer

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice clean room with tons of historic charm. Love the duvets and view to Millennium Park
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Jane

Liked: Cleanliness, staff & service
Enjoyed our stay. Bummed that the bar/restaurant was closed for renovations though. Otherwise, the hotel was in a great location, clean rooms, comfy beds, overall good experience!
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

MICHELE

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very clean and staff was very friendly.
Stayed 1 night in Nov 2025
Verified

10/10 Excellent

cheryl

Liked: Cleanliness, amenities, property conditions & facilities
Friendly, helpful staff, great bedding, perfect location especially if you're visiting the Christkindlmarket
Stayed 3 nights in Dec 2025