Staypineapple, An Iconic Hotel, The Loop

Hotels
•
StayPineapple Hotels
9 (1619 reviews)
1 West Washington , Chicago , us
+1 312-940-7997

listing image 1
Show all photos
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 1619 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
L
Lucas • family_with_children • us
8
Great location and wonderful view from hotel room.
Pros:

Wonderfull staff and architecture and design of hotel. Great Location and loved our view from our room (able to see Chicago Theatre). Close to train station. Walking distance to Millennium Park and a brisk, longer walk to Riverwalk. Stores and restaurants in surrounding area.

2026-07-25 • via Nuitee
C
Catherine • couple • us
9
Pros:

The most comfortable beds I have ever slept in! Amazing guest service- responsive and natural. Great location!

Cons:

The bathrooms need a bit of an update.

2026-07-23 • via Nuitee
L
Linda • solo_traveller • us
10
2026-07-23 • via Nuitee
L
Linda • extended_group • us
9
We loved the kindness of the staff, the location and the comfortable room.
Pros:

The employees were very kinds and helpful. The room was also very comfortable

Cons:

I know parking is at a premium but $75 for parking seems a bit excessive

2026-07-20 • via Nuitee
A
Arne • couple • se
9
Pros:

Fantastisk frukost. Trevlig personal. Sköna sängar.

2026-07-17 • via Nuitee
B
Bastemeijer • solo_traveller • ca
8
Great location, friendly staff
Pros:

Location is perfect

Cons:

Carpet on the floors not hygenic, a bit warn down

2026-07-17 • via Nuitee
T
Timur • solo_traveller • gb
9
2026-07-15 • via Nuitee
R
Robert • extended_group • gb
8
2026-07-15 • via Nuitee
L
Lesko • solo_traveller • us
10
Pros:

location was close to everything, had valet parking for 75 dollars extra, lobby was nice, bed was soft and so was the robes.

Cons:

small elevator

2026-07-13 • via Nuitee
M
mcal924 • Family
10
Great hotel and great location
Pros:

I am 100% satisfied. From beginning to end we enjoyed our stay.

2026-07-11 • via Tripadvisor
A
Allan • couple • ca
9
Superb location, and a clean but small room.
Pros:

The hotel is located in an excellent location just minutes away from a bunch of attractions, including Millennium Park. My room was very clean, and towels and linens were changed daily, even though the hotel says they only do it every other day. I can’t remember the last time I got a physical key for a hotel room, and I didn’t think I would like it as much as I did having a brass key for my room. The room rate was very reasonable, considering my related complaint below. The staff were very kind as well. The pineapple theme of the hotel was pretty cute.

Cons:

My room was small and it was fairly claustrophobic. Also, there were multiple events happening during the weekend of my stay, so this hotel and most other hotels in downtown Chicago jacked up their prices VERY high compared to their usual rates - that said, the Staypineapple’s rates were among the lowest in this location.

2026-07-08 • via Nuitee
B
Busjahn • solo_traveller • us
10
2026-07-08 • via Nuitee
U
Ulrike • couple • de
10
2026-07-08 • via Nuitee
M
Mitchell • solo_traveller • us
10
2026-07-06 • via Nuitee
A
Amiee • solo_traveller • us
9
Pros:

We love the duvet comforters and the amenities.

2026-07-06 • via Nuitee
N
Nathalie • solo_traveller • ch
8
2026-07-06 • via Nuitee
C
cheryllG7380OC • Solo travel
8
Nice hotel, large rooms with tall ceilings, convenient to LAX. Safe area.
Pros:

Location great. Complimentary airport shuttle came quite soon and driver was helpful and loaded all luggage for clients even those who could do it themselves.
Simon was very helpful to me at front desk.

2026-07-05 • via Tripadvisor
K
karenkI747UD • Family
10
Fantastic weekend girls trip with daughter
Pros:

My 13 year old daughter and I absolutely loved our 3-night stay at Staypinapple. Located in the heart of the downtown loop, very close to shops, the park, museum, and the river walk- perfect for us to easily walk from place to place. Sashon at the front desk was very warm and friendly and made us feel welcomed immediately. Special touches like the free pineapple-shaped cookies at 3pm (amazing!!) and an umbrella provided for an unexpected rainstorm were very thoughtful. I would like to emphasize the extremely comfortable bedding- wanted to take the duvet home with me! We will definitely be back!

2026-07-05 • via Tripadvisor
L
Linda • couple • gb
9
Nice stay at Staypineapple.
Pros:

Nice hotel in a good location. The bed was very comfy and you could get free water refills in a chiller bottle they supplied. There was a fitness room although it was very small and I’m not sore there was aircon

Cons:

Nothing.

2026-07-05 • via Nuitee
N
NYTravelGrl23 • Family • Orchard Park, New York
10
Incredible!
Pros:

Comfortable, convenient oasis in the middle of the bustling city! Luxuriously comfortable beds, quiet rooms. Friendly reception, and great amenities! We enjoyed utilizing bikes, fitness center, and the happy hour cookies and coffee. The hotel restaurant and welcome drink were greatly appreciated! This is our second time staying, and we will definitely say again.

2026-07-03 • via Tripadvisor