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Staypineapple, An Iconic Hotel, The Loop

4.0 star property

Choose dates to view prices

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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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, multilingual staff, and free newspapers
    • Luggage storage, coffee/tea in the lobby, and a front-desk safe
    • 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
    • Free infant beds, housekeeping, and desks

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

As of May 22, 2026, prices found for a 1-night stay for 2 adults at Staypineapple, An Iconic Hotel, The Loop on May 25, 2026 start from $197, 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 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

Reviews

9.4

Exceptional

9.6

Cleanliness

9.0

Amenities

9.6

Staff & service

9.4

Property conditions & facilities
Rating 10 - Excellent. 823 out of 1069 reviews
Rating 8 - Good. 160 out of 1069 reviews
Rating 6 - Okay. 51 out of 1069 reviews
Rating 4 - Poor. 16 out of 1069 reviews
Rating 2 - Terrible. 19 out of 1069 reviews

Reviews

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

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

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

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

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

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

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

Kathleen

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

10/10 Excellent

James

Liked: Staff & service
Very friendly and courteous staff. The room was beautiful and very comfortable. We had a view of the lake in millennium Park the perfect place to stay!
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Marquette

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Clean, easy checkin, great staff
Stayed 1 night in Dec 2025
Verified

10/10 Excellent

Susan

Liked: Cleanliness, staff & service, amenities
Rooms were very comfortable. The staff was very friendly upon check in. Loved the location to everything downtown.
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Lauren

Liked: Cleanliness, staff & service, amenities
Hotel was great, bedding was very comfortable. I have trouble sleeping in hotels where the bed is too firm or sheets are too stiff, they did a great job with comfort.
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Anthony

Liked: Cleanliness, staff & service, amenities
Fantastic location, excellent service, great clean room w/ comfortable bed. For the price this was a great stay and would definitely go back. The restaurant/bar was pretty good too!
Stayed 2 nights in Dec 2025
Verified

10/10 Excellent

Christiano

Liked: Cleanliness
Clean room, helpful staff
Stayed 3 nights in Jan 2026
Verified

8/10 Good

Sarah

Liked: Cleanliness, staff & service
Disliked: Amenities
This property is in a great location. The staff were friendly and the room was clean. The room we were in was very small and used. The building is really cool but we were super disappointed with it being under construction with no place to hang out and have a drink. We weren’t notified of the construction until right before our stay. We would have chosen somewhere else because of this.
Stayed 3 nights in Apr 2026
Verified

10/10 Excellent

Richard

Liked: Cleanliness, property conditions & facilities
Great location, clean, and very helpful and friendly staff
Stayed 2 nights in Nov 2025
Verified

10/10 Excellent

Aidee

Liked: Cleanliness, amenities, property conditions & facilities
This is my favorite hotel downtown. I book here when I can. The hotel is clean and the architecture is so beautiful. Stay is always welcoming and you get a free drink from the bar as well as cookies!
Stayed 1 night in Dec 2025