Staypineapple, An Iconic Hotel, The Loop

Hotels
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StayPineapple Hotels
9 (1596 reviews)
1 West Washington , Chicago , us

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Children allowed
Pets allowed

Facilities

Fitness facilities
WiFi available
Free WiFi
Parking
Non-smoking rooms
Air conditioning
Fitness center
24-hour front desk
Heating
Pets allowed
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.
A deposit may be required at the property.

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 1596 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
K
Karl • solo_traveller • us
9
Excellent location in a classic building.
Pros:

Location is perfect.

Cons:

No free breakfast option included

2026-06-27 • via Nuitee
2
2skinnylegs • couple • us
9
We appreciated and chuckled at the sense of humor and the small touches.
Pros:

Hotel location was convenient. We knew room would be small and, while it was, it was sufficient. The hotel is old and that adds to its charm. It was clean so that adds to my comfort. The bed, as many guest report, is super comfortable, as are the bed linens. The staff is very friendly and knowledgeable.

Cons:

Except for one small washcloth, the towels could use a refresh. The hotel is old and charming but the towels don't need to be old and look old. They appeared clean, just frayed. Newer, softer towels would be a visible improvement.

It wasn't a surprise but we didn't appreciate the daily amenity charges. We didn't use the amenities and, when we reviewed the final receipt, they did add quite a chunk to an already expensive bill. Perhaps rethink that charge?????

2026-06-25 • via Nuitee
H
Hazel • extended_group • us
8
2026-06-24 • via Nuitee
J
Jennifer • solo_traveller • us
10
2026-06-24 • via Nuitee
M
Maio • family_with_children • us
8
We would def stay there again, hopefully in newer version of it.
Pros:

Location is amazing as well as staying in an beautiful iconic building with a great view.

Cons:

Hotel probably needs un upgrade, too expensive for what it is and what amenities provides.

2026-06-23 • via Nuitee
J
Jeremy • solo_traveller • us
9
Good base for The Loop
Pros:

Great location in iconic building.
Staff was great.

Cons:

Room ceiling had water stains on them…made it feel like an old motel.

2026-06-21 • via Nuitee
G
Geoffrey • couple • gb
9
Will stay on our next trip to Chicago
Pros:

Excellent location for our purposes. Staff generally good but an issue regarding additional charges took longer than it should to resolve

Cons:

Restaurant nothing to do with hotel

2026-06-19 • via Nuitee
F
Fiona • couple • au
9
2026-06-17 • via Nuitee
R
Rachelle • family_with_children • us
10
2026-06-15 • via Nuitee
O
Olivia • solo_traveller • it
10
Pros:

Nice room but common areas unavailable all was underconstruction

Cons:

Loved the room should advertise breakfast is not possible since lobby is under heavy construction

2026-06-15 • via Nuitee
R
Roxane • couple • us
9
2026-06-12 • via Nuitee
L
Lisa • solo_traveller • us
9
2026-06-09 • via Nuitee
J
Jose Ignacio • family_with_children • es
9
2026-06-09 • via Nuitee
J
Julie • family_with_children • us
10
Happy
2026-06-09 • via Nuitee
C
Connor • couple • us
8
2026-06-07 • via Nuitee
P
Pauline • couple • us
10
We were comfortable and centrally located
Pros:

Cozy, comfortable, the beds were super comfortable

Cons:

Bathrooms could use an upgrade

2026-06-02 • via Nuitee
H
hellomoto88 • Family • Ipswich, Massachusetts
10
Wonderful!
Pros:

We went to New York to celebrate my daughter's 30th birthday, and we had a great stay. The hotel location was perfect: around the block from the train station, close to many attractions and restaurants, and tons of retail stores on the same street. The room was very quiet and clean. The front desk was very friendly and helpful. They even left a cute surprise for my daughter. Thanks for a great trip!

2026-05-29 • via Tripadvisor
T
Tsuyoshi • solo_traveller • jp
9
シカゴの思い出を華麗に彩る額縁🖼️
Pros:

立地が抜群です！
そしてシカゴ建築の象徴・あのシカゴ窓から眺めるループ内の景色は何ものにも代え難い至福。シカゴに何度も行けるならここじゃなくても良い。
でも一生に一度のシカゴなら僕はここを勧める。

Cons:

ぬいぐるみはいらないかも笑

2026-05-28 • via Nuitee
B
Brianna • couple • us
10
2026-05-27 • via Nuitee
M
MeganinMSP • Family • Minneapolis, Minnesota
10
The staff is fantastic!
Pros:

100/100! Another fantastic stay where the staff went above and beyond. We’ve stayed here multiple times and everyone is always so friendly and helpful. They surprised us with some extras this trip and the timing couldn’t have been more perfect given some stressful events the week prior. The new restaurant is great and as always the location can’t be beat. Love staying in a historical hotel and look forward to a return stay late summer.

2026-05-25 • via Tripadvisor