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  5. Reviews of Staypineapple, An Iconic Hotel, The Loop

Reviews of Staypineapple, An Iconic Hotel, The Loop This rating is a reflection of how the property compares to the industry standard when it comes to price, facilities and services available. It's based on a self-evaluation by the property. Use this rating to help choose your stay!

1 West Washington, Chicago Loop, Chicago, IL 60601, United States

#30 of 184 hotels in Chicago

Guests' Choice

Review Score

Based on 846 hotel reviews

8.9

Score breakdown

  • Cleanliness

    9.1

  • Comfort

    9.1

  • Location

    9.7

  • Facilities

    8.8

  • Staff

    9.0

  • Value for money

    8.4

  • Free Wifi

    8.8

Verified guest reviews from real Bookers

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Showing 1 - 25

  • Reviewed: March 30, 2025

    8.0
    Very Good
    • Leisure trip
    • Solo traveler
    • Deluxe Queen Room
    • Stayed 2 nights
    • Submitted from a mobile device

    Generally a good stay. Some kind of a noise in the room which appeared to come from next door. Maintenance were very helpful dealing with it on the first day but it was back again the next day.

    Stayed in March 2025

  • Reviewed: March 28, 2025

    10
    the perfect spot in Chicago downtown
    • Business trip
    • Solo traveler
    • Deluxe Queen Room
    • Stayed 4 nights

    nothing

    probably the perfect spot in Chicago downtown. Easy links to everywhere Great to walk around the downtown I like old style hotels and this is very well

    Stayed in March 2025

  • Reviewed: March 20, 2025

    9.0
    The best place to stay in Chicago. Super friendly staff!
    • Leisure trip
    • Solo traveler
    • Deluxe Queen Room
    • Stayed 5 nights
    • Submitted from a mobile device

    Location, location, location. Near metro, theatres and park.

    Stayed in March 2025

  • Reviewed: March 20, 2025

    8.0
    They may change you $25 dollars when u check in
    • Leisure trip
    • Couple
    • Deluxe King Room
    • Stayed 1 night
    • Submitted from a mobile device

    Forced to change addition $25 dollars for this visit. Still not clear what is this about

    Clean and nice hotel

    Stayed in March 2025

  • Reviewed: March 4, 2025

    10
    Great Chicago experience for the theater district, shopping, restaurants and sight seeing.
    • Leisure trip
    • Couple
    • Deluxe King Room
    • Stayed 1 night
    • Submitted from a mobile device

    No complaints.

    Location and amenities were outstanding.

    Stayed in March 2025

  • Reviewed: February 24, 2025

    10
    Always a Great experience at this Historic place.. One of my most favorite of all places to come and visit.
    • Leisure trip
    • Couple
    • Deluxe King Room
    • Stayed 2 nights
    • Submitted from a mobile device

    Location was Excellent!!

    Stayed in February 2025

  • Reviewed: February 23, 2025

    10
    Great, can’t wait to come back again!
    • Leisure trip
    • Couple
    • Deluxe Queen Room
    • Stayed 3 nights
    • Submitted from a mobile device

    Nothing

    Such cool architecture, cozy rooms, great staff, delicious food! Not my first time there and definitely not my last!

    Stayed in February 2025

  • Reviewed: February 17, 2025

    9.0
    Great hotel.
    • Leisure trip
    • Couple
    • Deluxe Queen Room
    • Stayed 2 nights
    • Submitted from a mobile device

    Cable TV was spotty during NFL playoff game.

    Location. Cleanliness. Comfort.

    Stayed in January 2025

  • Reviewed: February 15, 2025

    10
    Exceptional
    • Leisure trip
    • Family with young children
    • Deluxe Queen Room with Two Queen Beds
    • Stayed 4 nights
    • Submitted from a mobile device

    Nothing

    The property was unique and architecturally amazing!! Loved the layout of the floors and our room was a perfect corner with an amazing view!!

    Stayed in December 2024

  • Reviewed: February 11, 2025

    9.0
    My stay was very comfortable and restful.
    • Business trip
    • Solo traveler
    • Deluxe Queen Room
    • Stayed 2 nights
    • Submitted from a mobile device

    N/A

    The property was in a good location. Everything was working, clean, and easily accessible.

    Stayed in February 2025

  • Reviewed: February 8, 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • Deluxe Queen Room
    • Stayed 1 night
    • Submitted from a mobile device

    There isn't anything I didn't love.

    Everything. I can't say enough good things about this hotel. It has definitely set the bar for what I look for in a hotel stay.

    Stayed in January 2025

  • Reviewed: January 28, 2025

    9.0
    A beautiful, stylish, and comfortable hotel in the vibrant heart of downtown Chicago.
    • Leisure trip
    • Solo traveler
    • Deluxe Queen Room with Two Queen Beds
    • Stayed 2 nights

    The room was a little dark. It could benefit from another lamp or two. The surrounding area is pretty noisy with street musicians etc. (although that is part of the excitement of being in a big city).

    I love the location of the hotel. You really feel in the thick of things. Since it was the holidays, the decorations were really fun. I appreciate the little touches like cookies in the afternoon. The public area is comfortable and was very cozy despite the cold weather. I love the whole vibe of the hotel. Best hotel beds I've ever slept in! Also, I had a great view of the NYE fireworks from my window!

    Stayed in January 2025

  • Reviewed: January 23, 2025

    9.0
    Excellent couple nights in great location.
    • Leisure trip
    • Group
    • Deluxe Queen Room with Two Queen Beds
    • Stayed 2 nights

    Only comment here was some noisy activity in early morning on a Saturday was annoying. Not sure what it was, but sounded like slamming on something.

    Great locale and rendezvous spot. Comfort and amenities. Friendly staff.

    Stayed in January 2025

  • Reviewed: January 22, 2025

    10
    Exceptional
    • Leisure trip
    • Couple
    • Deluxe Queen Room
    • Stayed 3 nights
    • Submitted from a mobile device

    It was very convenient for location purposes everything was walking distance

    Stayed in January 2025

  • Reviewed: January 19, 2025

    10
    Exceptional
    • Leisure trip
    • Family with young children
    • Deluxe Queen Room with Two Queen Beds
    • Stayed 1 night
    • Submitted from a mobile device

    Nothing

    The staff was amazing

    Stayed in January 2025

  • Reviewed: January 17, 2025

    8.0
    Very Good
    • Leisure trip
    • Couple
    • Deluxe King Room
    • Stayed 1 night
    • Submitted from a mobile device

    Parking was off site and took a while when checking out to bring my vehicle back. There is also nowhere to park to have the valet, had to wait in the street. They also ended up double charging me for parking as I tried to pay ahead of time during the online booking confirmation.

    The bedding was super comfortable and nice. The staff were excellent.

    Stayed in December 2024

  • Reviewed: January 6, 2025

    9.0
    A hotel with charm and character in downtown Chicago
    • Leisure trip
    • Couple
    • Deluxe Queen Room
    • Stayed 4 nights

    Had a great time at the StayPineapple in downtown Chicago. The hotel is perfectly located for some urban exploration of The Loop. Most tourist hotspots were within walking distance, and the subway (just a 2-minute walk away from the hotel) made it easy enough to visit the attractions further out. During our 4-night stay we had no complaints about the room either. While the bed was not oversized, it was comfortable, and the air conditioning was efficient in cooling down or warming up the room. The building shows its age, especially in the bathroom facilities, but – at least for us – that only adds to the charm and character of this hotel. We did not try the breakfast or the restaurant, so no comment there. Overall we had a 5-star experience and the hotel lived up perfectly to our expectations. We wouldn’t hesitate to book again.

    Stayed in December 2024

  • Reviewed: December 22, 2024

    10
    Christmas in the city
    • Leisure trip
    • Family with young children
    • Executive King Suite - Disability Access
    • Stayed 2 nights
    • Submitted from a mobile device

    Thermostat is a little touchy. Hot/cold

    The views in 904 absolutely stunning! Chicago Theater to the North and Millenium Park Christmas tree, Lake Michigan and Pritzker Pavilion to the East!!! Christkindl Market out the front door. The Atwood restaurant downstairs just wonderful. At Christmas perfect

    Stayed in December 2024

  • Reviewed: December 21, 2024

    8.0
    Very Good
    • Leisure trip
    • Couple
    • Deluxe Queen Room
    • Stayed 2 nights

    location, cleanliness

    Stayed in December 2024

  • Reviewed: December 13, 2024

    10
    If you’re looking for a beautifully preserved, well located, clean, that has a superb on-site restaurant, then look no f
    • Travelers with friends
    • Deluxe Queen Room
    • Stayed 2 nights
    • Submitted from a mobile device

    I loved everything

    The hotel is iconic. They have mixed old and new decor — it’s outstanding!! You simply can’t beat the location

    Stayed in December 2024

  • Reviewed: December 13, 2024

    9.0
    I loved my stay at this hotel. I promptly ordered a bathrobe and stuffed dog. Thanks for the water bottle!
    • Leisure trip
    • Solo traveler
    • Deluxe Queen Room
    • Stayed 5 nights
    • Submitted from a mobile device

    No microwave :(

    Great location Afternoon snack!! Bathrobes!!

    Stayed in December 2024

  • Reviewed: December 9, 2024

    10
    Exceptional
    • Leisure trip
    • Family with young children
    • Deluxe Queen Room with Two Queen Beds
    • Stayed 1 night
    • Submitted from a mobile device

    Nothing to mention

    Such a beautiful hotel love the nostalgic feel of this place. An amazing stay started from the moment you walk in the door we will definitely be back next year!!

    Stayed in December 2024

  • Reviewed: December 9, 2024

    10
    Great location, great staff, would stay again
    • Leisure trip
    • Couple
    • Deluxe King Room
    • Stayed 1 night

    We got to the hotel a little earlier than the 4 pm check in time and they were able to accomodate us and let us into a room that was ready. We loved the staff, the free welcome drink, and the room itself. It had an amazing view and the bed itself was super comfy.

    Stayed in December 2024

  • Reviewed: December 9, 2024

    10
    Our favorite stay when when we come to Chicago!
    • Leisure trip
    • Couple
    • Executive King Suite - Disability Access
    • Stayed 2 nights
    • Submitted from a mobile device

    Close proximity to Christkindlmarket,Macy’s, excellent dining options! Big comfortable rooms. Excellent staff that were friendly and knowledgeable. Love the nostalgic feel in a hotel with a real key!

    Stayed in December 2024

Showing 1 - 25

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