Staypineapple, An Iconic Hotel, The Loop

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

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
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
U
Ulrike couple de
10
2026-07-08 via Nuitee
B
Busjahn solo_traveller us
10
2026-07-08 via Nuitee
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
N
Nathalie solo_traveller ch
8
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
M
Mitchell solo_traveller us
10
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
A
Anja family_with_children de
9
Pros:

Perfekte Lage im Zentrum.

2026-07-03 via Nuitee
D
Dreamer28733245110 Business Onancock, Virginia
10
Business GFOA to Chicage
Pros:

I was looking for an historic building with a special flair. The Staypinnaple exceeded all expectations. From the front desk, pineapple cookies & especially the room i was very impressed.

2026-07-02 via Tripadvisor
K
Kristine couple us
9
Pros:

Great location. Quirky.

Cons:

N/a

2026-07-02 via Nuitee
P
Passport35211569114 Solo travel
10
A lovely experience
Pros:

Terrific location. The blue line from O'Hare pops you out within rock-throwing distance of the hotel. The place has a much more cozy feel than the Palmer House, but also exudes a historic aura. Loved the view through the extra tall windows in my room. And the 8th floor reminded me of the historic Mechanics Institute Building in San Francisco, complete with an old-fashioned key with a pineapple fob. Enjoyed the small touches like the refillable pineapple-branded water bottles and the refilling station near the bar (including a sparkling water option), the sweet stuffy adorning the comforters, and the unique coffee maker that's unlike any other I've seen to date in a hotel. The bed was comfortable. Wish I could have enjoyed the afternoon cookies (but alas, I must eat gluten free). Management treated me to a lovely surprise, a bottle of wine, some additional goodies, and a note wishing me well for my book signing at the American Library Association conference. As a woman traveling solo for business, the place felt safe and welcoming. I'll definitely be back and recommend this hotel to my friends.

2026-06-30 via Tripadvisor
2
215faither Business
10
Dreaming, of coconut rice
Pros:

Such a great stay. Beds are out of this world. I don’t typically sleep well, not a problem on this trip. Love the location. And I’ll dream about the coconut rice at Mariela.

2026-06-30 via Tripadvisor
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
L
loram566 Family
10
Beautiful and convenient
Pros:

Great hotel in architecturally historic building and in a great location. Our room was a good size and everything was immaculate and clean. Great view over with city too,. Highly recommend this hotel for anyone visiting Chicago,.

2026-06-26 via Tripadvisor
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
J
Jennifer solo_traveller us
10
2026-06-24 via Nuitee