Staypineapple, An Iconic Hotel, The Loop

The hotel itself was amazing. Very clean and well taken care of. The staff was fine, not bad, not good. My complaint is regarding the valet service. We had to wait a long time for the valet to take our car when we arrived and it was 20-25 minutes to get it for us when it was time to leave. That is frustrating.

VERY small and old rooms. Towels smelled awful. Dingy carpets. Zero functioning amenities. Staff was very unhelpful. Called the front desk at 11 pm to ask for help with the streaming service and was told, "It's late. Call back in the morning." The only redeeming quality was the location. I wouldn't have such a negative impression of the hotel if it was rated two stars but it was rated as "exceptional" and that is 100% inaccurate. Holiday Inn Express vibes at best.

That said, the staff was wonderful. We were getting ready to go out Saturday night for dinner and drinks when the dress I planned to wear suddenly had a tear. Thankfully, housekeeping was cleaning the room next to us, so I stepped out and asked if they happened to have a sewing kit. She immediately called a colleague, and within less than 10 minutes, I had one in my hands — truly my saving grace! The staff was very sweet, and they do a great job keeping the place clean and tidy. I also appreciated how conscientious they were about water bottle preservation, and the water filling station was actually really nice, with options for different water temperatures, sparkling, or still. Overall, we had a great time. Thank you — we will definitely be back!

Beautiful historic hotel building, lovely room and amenities in room. Bar and restaurant were awesome, great food, drinks and vibe. Will stay here again!

Great location in iconic building. Staff was great. Room ceiling had water stains on them…made it feel like an old motel.

Location is perfect!!! Directly adjacent to bus and train. Held our bags both before check in and after checkout. The hotel and rooms are quirky and fun, everything was very comfortable and we enjoyed it. The breakfast restaurant (not included) was spectacular!!!

The hotel is lovely and our room was clean and comfortable. It's within easy walking distance to the Chicago Theater which is why I chose it. Ate breakfast at the small but sunny restaurant and it was reasonable and very tasty. I recommend this place for a cozy downtown stay.

Very clean and very helpful staff-resturant was wonderful. Coffee maker and bed shams???

Excellent location for our purposes. Staff generally good but an issue regarding additional charges took longer than it should to resolve Restaurant nothing to do with hotel

Always very nice, great location and building

Great staff! Hosted at restaurants was excellent ‘!

Superb

Fantastic place to stay, especially if you are looking to walk around the city. Super convenient location and amazing accommodations. The staff were super helpful and valet parking made getting in and out super easy.

We loved character of the building and the proximity to downtown. However the hotel was not as secure as others. Anyone from the public could access elevators. Also a $25 amenities fee was attached for cookies, water, and bikes. We did not need or use any of these.

I'm officially a Staypineapple fan! Great branding. Attentive, capable staff, cool vibe. Awesome location.

Nice room but common areas unavailable all was underconstruction Loved the room should advertise breakfast is not possible since lobby is under heavy construction

Exceptional

Room was clean, and comfortable although quite small. Valet parking was terrible despite being costly, the “free” amenities have a value of perhaps 5 dollars but the “amenity” fee is $25.00. Taxes, non-optional fees, parking costs, etc can easily make the final costs more than 150 per cent of the advertised price for a night’s stay, and lack of a doorman, any bellmen, at most two front desk people, and one valet make this a hotel that has nice rooms and no service and much personal inconvenience. Being hip and cute is not good enough.

Stylish architecture and details of historic building. Convenient to subway stations.

Darnell at the front desk was so warm and helpful. Our room was as pretty and cozy as it gets, the view to die for. The restaurant downstairs has the best French toast on earth. For reals!