Staypineapple, An Iconic Hotel, The Loop Chicago

I am not exaggerating when I say this was the best hotel I’ve ever stayed in and I will be planning future trips AROUND cities that have staypineapple hotels. The bedding was so comfortable I didn’t want to leave even with our exciting vacation plans. The hotel itself was stunning, historic, and in a great location. The service was spectacular. Of course, I was thrilled with the daily sugar cookies and reusable water bottles. Our room also had a cute dessert welcome plate prepared for us when we arrived. I will not stop talking about this place. THE BEST!

What a delight! I just returned from an epic Chicago weekend and am so glad I decided to stay at the Stay Pineapple in Chicago! The location is incredible, within walking distance to plenty of shopping, museums and the theater. The building is super cool, as they say in their title, its iconic, it truly is, and I love the personal touches, I checked in and had a lovely welcome note, a refillable water bottle, the comfiest beds ever, and really nice bathroom linens. The cherry on top of the experience has to be the staff though, they were so engaging and friendly! I had to wait for a car and I saw them welcome and chat with guests, truly remembering them and checking in on them. I will be back!

Clean and comfortable location. The bed and duvets are such a comfort, I elected to spend more time in bed than going out early morning in the cold. The gentleman at the front desk during my stay were courteous and friendly, and made check in and check out a breeze. Baggage hold after check out was very appreciated, as it allowed me to explore the city for a few more hours. Location is fantastic for public transportation and walking, I didn't uber until leaving with all my bags. There is everything you really need within a block, but you definitely want to explore beyond that. I wish I could have stayed longer, but, you know... responsibilities. The hotel itself respects the building it's in, and it's a quite lovely decorated and maintained. As someone who appreciates architecture, it's gorgeous. As it is an older building, there may be some slight oddities or things that need to be addressed, however I didn't encounter any issues during my stay. I booked a room through the phone line as the website was glitching out on me a bit, and she made it simple and easy. Be careful, as the hold line jingle is a bit catchy. If I'm in town and the location works, this would absolutely be my first choice to check to see if there's room available. Would recommend!

I had a pleasant stay at Staypineapple. The hotel was conveniently located in the heart of town. It was walking distance to major tourist attractions and 2 train stations. Checking in and out was easy and smooth. The room was clean and spacious. I appreciated the welcome drink and afternoon cookies and coffee. Highly recommended! 

My husband and I had been driving for upwards of 12 hours and were just looking for a place to sleep for the night. My husband and I are almost 19, so finding a hotel that had an age requirement of 18+ rather than 21+ proved to be extremely difficult. I was incredibly relieved when I called the StayPineapple and found out that you only needed to be 18 to check in. However, upon arrival the front desk agent looked over our ID’s and after doing the math in his head concluded that we were under 18. I insisted that his math is wrong and that he needed to get on his computer to verify this, but he continued to tell me that the math in his head seemed right and that we couldn’t be of age. His computer would have told him that anybody born in 2007 will be turning 19 this year, 2026. We told him that we are legally married, regardless of all of this it took him almost 10 minutes before he decided to finally let us check into our room. The next morning we had to wait over an hour in the lobby before our car was returned to us. Hotel was in a good location. We were put on the 11th floor. Room was fine, beds are small but comfortable. No view like the photos showed. If you take the stuffed animal they place on your bed they charge you almost $30.

I always enjoy staying at Hotel Pineapple when I come to San Francisco. The staff consistently create a welcoming and comfortable environment, and the hotel is clean, peaceful, and close to everything. There is no better environment or hotel to stay in when traveling. On this special occasion, Nixxy and Brian went above and beyond. My travel plans were unexpectedly delayed by an entire day, and they made sure I had safe, secure, and comfortable accommodations while I worked through rebooking. Their kindness, professionalism, and genuine care made all the difference during a stressful time. Because of them, I will always stay here. Hotel Pineapple truly provides an exceptional experience.

My 2 year old daughter and I had a wonderful stay at this hotel. The staff were incredibly kind. The front desk attendant, Sashon, took great care of us when we arrived. He helped us get all our luggage in, checked us in, brought our luggage to our room, and then brought us milk and cookies! There was a stuffed animal and candy canes waiting for my daughter in our room as well. He also continued to check in on us throughout our stay. Our room faced state street and Macy's, which my daughter loved. They had a crib for her, and the bed for me was very comfortable. The room was very clean. When we were checking out, the cleaning woman offered to help us get our luggage downstairs. I was so grateful as it was difficult to juggle everything and keep an eye on my little one. I was so impressed with the staff and how well they took care of us. We will definitely return to this hotel.