Staypineapple The Loop Chicago

We came in for our wedding anniversary and the first night (Thur) was absolutely wonderful however we left on Sunday and our room hadn't been cleaned at all. We had to call twice for fresh towels. Its hard to celebrate the time away when you're room doesn't get cleaned at least once. I will say that the restaurant and its staff were amazing!

Staying here at the moment and the location is great but that's where the positives end. I'm in literal disbelief that this place is so highly reviewed. From the moment you arrive, the front door is old and tattered, there's no security or valet or anything, and you enter the lobby, which is a construction site and there is stuff just thrown everywhere. There is absolutely no effort from the workers to have the place in any way tidy, like it's almost as if they've gone out of their way to make the place as uninviting as possible. The reason it's a construction site is because the restaurant area is being renovated, something which wasn't communicated to me at any point until I arrive into the filthiest lobby I've encountered in over 1000 hotel stays. Seemingly this was supposed to be open by now but I'm not remotely surprised, given the absolutely atrocious standards this hotel operates in, to learn it isn't ready on time. Then everything is so old and dated in the rooms, the bathroom especially is absolutely horrific. There was hairs in the bathtub when we arrived, which is just absolutely disgusting and makes me wonder about the housekeeping, and then if you dare to actually use the shower you'll need earplugs because the water heater when the shower is turned on can probably be heard several blocks away, it's absolutely crazy how loud it is, and how strong the vibrations are. Worse again, is that other rooms using their shower, toilet or sink even creates huge sound in your room and in the case of them using the shower, it will have your walls literally vibrate. I'm not joking, this nonsense could be measured on the richter scale. The bathroom themselves are in serious need of renovation. The room is dark and poorly lit, with a carpet that looks like it's been laid since the building was built, however many decades ago that is. I genuinely feel like I've been scammed by the positive review score but it's probably my fault for not reading some of the more recent ones which reflect the grim reality here. Another review wondered if the hotel was paying for reviews and while I wouldn't go as far as to make that accusation, I find it truly baffling that this place is as well reviewed as it is. The hotel is too concerned about silly things like toy dogs (which cost $25, as if you haven't been scammed enough by now) than actually focusing on the important things. If you are reading this and there's something else in your price range with similar reviews then go with that. Edit - Just wanted to note that although the manager mentions in her reply that she would reach out to me directly, unsurprisingly and consistent with the level of service associated with this hotel, she never did.

Shocking how much I loved this little boutique hotel!!! My stepdaughter and I spent the weekend exploring Chicago. April in housekeeping and Darnell at the desk couldn’t have been more accommodating and kind! You’ve got a lot of great people but these two made it ultra special. I even saw April out on the street as she was getting to work and she asked how my stay was and if there was anything else she could do to make it special, let her know. Great property with invaluable staff!!! Checkout at noon (rather than the typical 11 am) was ideal and I needed every second of that extra hour. Thank you Staypineapple. I bought a coffee mug and the stuffed puppy dog.

We loved our stay at Staypineapple! The bed was every bit as comfortable as advertised, and the room was wonderful. We also had an amazing view of downtown Chicago, which made our stay even more memorable. We ordered pizza in for dinner, sat at the end of the bed, and enjoyed the city lights—it was the perfect way to end the day. We would absolutely stay here again and highly recommend it!

Great location! An older building, but it’s charming. The staff is what puts it over the edge— DJ, Darnell, and Sharneice (spelling? She has a great bob haircut) were standouts. We had a long and rough travel day, and DJ’s warmth and helpfulness made all the difference when we had to get settled in. Darnell was able to point us in the right direction when we were turned around. Also the free drink at check-in is a great perk. The restaurant is also very tasty. Location is close to great shopping and a nice walk to great restaurants. We also had a great view of the Chicago theater from our room. Worth visiting and considering, if only for the staff!