Staypineapple, An Iconic Hotel, The Loop

10/10 Customer for life now! The first room I got put in had the most gorgeous view! I asked to be put in a room with 2 beds, and the first room had a bed and a pullout. They moved me right away, absolutely wonderful service. The beds are crazy comfy BTW, the blankets are the best part. Cool, fluffy, and amazing on bare skin. Sashon made the trip unforgettable, he really takes care of guests and gets to know everyone.

Exceptional Hospitality Staypineapple is my favorite place to stay when I visit Chicago. Besides its perfect location to enjoy all that the city offers, their thoughtfulness and level of service are exceptional. When booking online, I simply mentioned that part of our reason for visiting was so that my friend, who misses his homeland in Puerto Rico, could explore the Humboldt Park neighborhood known for its thriving Puerto Rican culture, shops, and restaurants. We were amazed and touched to find a variety of authentic Puerto Rican food, treats, and beverages. It was such a nice surprise and went above and beyond in terms of service. I highly recommend Staypineapple and will definitely return.

Great location, friendly staff Had a wonderful stay here for a girls weekend. We were immediately greeted by Darnell who was very friendly and welcoming. The hotel has great art deco style and a fun relaxing set up with the seating area and bar downstairs. It's in a great location for restaurants and metro stops. Very comfortable beds, and while I've read others complaints of the duvet, I actually found it very versatile and comfortable. There's a great water filling station (still and sparkle) by the bar.

Some great positives, like location, but too many negatives This hotel has some great positives - location is excellent, the building was beautiful and historic, it was clean overall, but the negatives just outweigh those when there are so many options in Chicago. First of all, I did not sleep well because they think they are in Scandinavia and only give you a down duvet, no flat sheet. I was far too hot to sleep with the duvet but then also cold because there is nothing else to use. This is America and we like flat sheets. I also did not appreciate the amenity fee that is not clearly stated up front. The amenities are things that probably no one uses or are not worth it, which I believe is the point, so the hotel can make more money. As others have said, I can buy my own $1 water bottle if needed, rather than be charged $25 a day. While our room had space for four guests, we were still charged a $30 extra guest fee for my son (three guests total). Plus another fee, which might have been a hotel fee or a government fee. I don't know because it doesn't say. Paying just over $700 for a two night stay in a small room (smaller than an average American hotel room) with a bathroom that needs updated just is too much, even if the location is good and the windows big. I understand Chicago is expensive and space is limited, but this was even more than NYC prices for a similar hotel. Again, it was fine but it definitely isn't anything special. I would not stay again.

The perfect Chicago hotel. Are you an older woman traveling solo to Chicago? Staypineapple is a perfect choice. It’s small, in a great location for seeing Chicago attractions. (I live in Indiana and visit Chicago frequently for theater and ballet.) The rooms are lovely and the Atwood Cafe is on site. You won’t mind dining alone in their lovely establishment. By the way, the building itself is quintessential Chicago, designed by Daniel Burnham. The hotel is a great choice for all travelers, but I want to encourage older women traveling solo in particular because you will feel safely at home the minute you walk in the front door.