Staypineapple, An Iconic Hotel, The Loop

Hotels
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StayPineapple Hotels
9 (1535 reviews)
1 West Washington , Chicago , us

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Children allowed
Pets allowed

Facilities

Fitness facilities (surcharge)
Non-smoking rooms
Air conditioning
Restaurant
Pets allowed
Lift / Elevator
Luggage storage
Facilities for disabled guests
Non-smoking throughout
Wheelchair accessible
See all facilities

Review Highlights

Pros:
Excellent location
Friendly staff
Well-maintained hotel
Cons:
Price concerns
Small room size
Missing amenities

Categories

Cleanliness
8.89
Multiple reviews mention the hotel is well maintained and clean.
Service
9.36
Numerous reviews highlight excellent and friendly staff.
Location
9.9
Guests repeatedly praise the fantastic location.
Room Quality
8.85
Rooms described as beautiful but some mention small size.
Amenities
8.38
Some concerns about missing comfort items in the room.
Value for Money
8.34
Some guests feel the price is high considering certain issues.
Food and Beverage
8.89
Breakfast and restaurant service received positive feedback.
Overall Experience
9.36
Overall satisfaction is high with many positive remarks.
* This sentiment is summarized by AI based on user reviews.
Updated at: 2026-01-06 21:54

Property Description

Historic Architecture and Luxury Design
Experience the grandeur of historic Chicago architecture at Staypineapple, An Iconic Hotel, The Loop. Designed by renowned architect Daniel Burnham, the hotel boasts mosaic floors and marble ceilings, offering a luxurious stay in the heart of Chicago's Loop.

Modern Amenities and Stunning Views
Indulge in the perfect blend of classic elegance and modern comfort in our rooms. Enjoy white and gray decor with mahogany furnishings, flat-screen TVs, and plush bedding. Upgrade to a suite for breathtaking views of Millennium Park and Lake Michigan.

Convenient Location and Special Amenities
Explore Chicago's top attractions with ease - from shopping on Michigan Avenue to visiting Millennium Park. Take advantage of our fitness center, bicycle rental service, and special perks for your furry friends. Don't miss out on experiencing Navy Pier and other nearby entertainment venues during your stay.

Book now for an unforgettable stay at Staypineapple, An Iconic Hotel, The Loop!

Important information:

Reservations for 10 rooms or more need to be contracted as a Group with the hotel directly.Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply.

Check-in and check-out hours:
Check-out: 12:00 PM
Airport code: ORD

Property Policies

  • Children and extra bed policy

    Children of any age are allowed.
    Children up to and including 17 years old stay for free when using an existing bed.
    You haven't added any cots.
    You haven't added any extra beds.

  • Pets

    Pets are allowed. Charges may be applicable.

  • Internet

    WiFi is available in the hotel rooms and is free of charge.

  • Groups

    When booking more than 9 rooms, different policies and additional supplements may apply.

  • Parking

    Private parking is possible at a location nearby (reservation is not needed) and costs USD 75 per day.

Location

Guest Reviews

9
Based on 1535 reviews
Cleanliness: 8.89
Service: 9.36
Location: 9.9
Room Quality: 8.85
Amenities: 8.38
Value for Money: 8.34
Food and Beverage: 8.89
Overall Experience: 9.36
A
Aromal Ram • solo_traveller • in
1
2026-04-17 • via Nuitee
A
ANA MARIA ISABEL • couple • us
9
Nice cozy hotel in a great location of Chicago. Walking distance to Millenial Park and the AIC and many restaurants.
Pros:

Fantastic location. Nice converted wrt deco building. Staff was very helpful and nice.

Cons:

May I suggest that they change the bedstand where the mattress was set on? The edges were really dangerously sharp. As in you can hit your leg a few times a day since the room is not large.

2026-04-17 • via Nuitee
A
Ang • couple • cn
10
2026-04-17 • via Nuitee
Z
Zrinka • family_with_children • hr
9
Pros:

Location, rooms/beds

Cons:

No breakfast

2026-04-15 • via Nuitee
J
Jacqueline • couple • us
10
Absolutely recommend.. quaint, cute, whimsical, staff-hospitable.
Pros:

Vintage aesthetic..

Cons:

Entrance… could be a bit more captivating… curbside could use more appeal.

2026-04-13 • via Nuitee
G
Gander • solo_traveller • us
10
Cons:

The lobby/bar was under construction.

2026-04-13 • via Nuitee
I
Inspire41364317527 • Family • Ann Arbor, Michigan
10
Pineapples mean Welcome!
Pros:

Fantastic stay. Darnell heldour lu before and after check in/out. We loved the water bar! e

2026-04-11 • via Tripadvisor
K
Kelly • solo_traveller • us
7
2026-04-11 • via Nuitee
P
Petra-Alexandra • extended_group • ch
8
Würde es wieder wählen. Sobald das Restaurant/Empfang neu fertiggestellt wurden. War z.Z. im Umbau.
Pros:

Kuschliges Bett. Lage vom Hotel.

Cons:

bessere Kosmetkprodukte im Bad. Eine Lampe mehr.

2026-04-09 • via Nuitee
V
Vallaci • couple • br
10
2026-04-08 • via Nuitee
I
IndianaNif • Couples
10
Warm welcoming and fun for downtown
Pros:

My husband and I stayed for a night to go see a concert downtown, and Staypineapple Chicago was *perfect* and exceeded our expectations.
Immediately at check in, staff was warm and welcoming, and the amenities are stellar. Being able to enjoy a complimentary drink and treat upon arrival was a welcome touch. And later on at night when we returned to our room from cold and rain, William at the front desk helped ensure we had what we needed to stay comfortable and to feel cared for during the rest of our stay.

The hotel was incredibly clean and comfortable—even the comforters are freshly laundered duvets which is a big deal for me as someone who dreads the typical gnarly looking comforters at hotels. And the fun decor and kitsche-y flare in a beautiful boutique space was lovely.

We will definitely be back and recommend to friends!

2026-04-04 • via Tripadvisor
M
Marla • couple • us
10
2026-04-03 • via Nuitee
K
Kevin • couple • gb
10
Pros:

Great location and comfy bed.

2026-04-02 • via Nuitee
D
De Ovando • couple • mx
10
2026-03-31 • via Nuitee
A
Abril • couple • ar
10
2026-03-28 • via Nuitee
N
nicolinat185 • Friends getaway
10
Excellent experience
Pros:

We stayed on Sat March 14th. Centrally located within the theater district. We also saw the river being dyed for St. Patrick's Day and did the architectural boat tour. Everything was within easy walking distance.

We received excellent service from Sashon & DJ who were very friendly and went above and beyond to make us feel welcome. They were very accommodating not only to us, but as I was waiting in line, I witnessed them helping other customers with directions and suggestions to local attractions.

This is the 2nd time we have stayed when seeing a show, and this is our go to when staying in the theater district. Rooms are very clean, with great views of the city. Beds are very comfortable. Will definitely stay again.

2026-03-24 • via Tripadvisor
K
khristianm2013 • Family
10
An Iconic Experience
Pros:

My wife got tickets to the Theater District and after reading several reviews, I booked a room at Staypinapple, Chicago. We were greeted by Sasoon and Darnell. My wife told them this was for my birthday and WOW! I would have thought these two and the entire staff, were in my family. What a wonderful experience. Our room was amazing and they even decorated it for my birthday! What a great experience! Totally recommend Staypinapple to anyone looking for "an Iconic experience."

2026-03-19 • via Tripadvisor
B
Bernard • couple • de
10
Pros:

very good

2026-03-18 • via Nuitee
D
David • solo_traveller • gb
9
Pros:

A charming old world hotel in an excellent location to explore Chicago. Nice theme and large rooms & bathrooms. Very pleasant reception and welcome

2026-03-18 • via Nuitee
B
Bernard • couple • de
9
2026-03-17 • via Nuitee