Staypineapple, An Iconic Hotel, The Loop

Amazing view and service with a fee surprise. The location was amazing, the staff was great, and the room view was amazing. The only thing I didn't like was the daily 30 amenity fee not disclosed by priceline that covers water and coffee which a regular hotel provides for free.

Magical weekend! The location was perfect for us on Thanksgiving weekend. We could walk anywhere and easily hop on the L. The minute we walked in was magical and when they handed us the “keys” to get into our room, the nostalgia feeling burst. Everything was spotless and the European style comforters were perfect. We had breakfast downstairs in the Atwood and it was great and not overly priced. Everyone that helped us through the weekend was smiling and so inviting. We will be back.

Staypineapple Chicago: Boutique Branding, Budget-Level Service. Poor Safety and Security. Honestly, I had no idea what to expect from such a small, niche brand. Even the name is confusing. Is it "Staypineapple" or "Iconic Hotel"? I don't know. The branding lacks clarity from the start. The building itself has undeniable character, and the location is exceptional—perfect for anyone doing holiday shopping or a Christmas-themed trip to Chicago. But that’s where most of the positives end. Despite an over-the-top emphasis on design and sexually suggestive, borderline swinger-themed marketing, this is a fairly no-frills hotel. They really need to tone down the provocative branding. Especially if they want families. Service is minimal. I’m not even convinced the front desk is staffed 24/7. There’s no doorman, no bellman and virtually no staff presence. The operating standard is closer to a 2.5-star roadside property—think Fairfield Inn or Holiday Inn Express but with a restaurant and bar. Housekeeping is only provided every other day. While the building’s historic character and the unbeatable location add charm, the rooms themselves are tired. Furnishings are worn with visible scuffs, scratches and stains. The bathroom had mold and mildew in the tub-shower area. Security is another concern. The hotel uses old-fashioned metal keys, and there is no keycard access required for elevators or stairs. Anyone can walk in and wander the floors. That’s a major safety issue. The worst part? You need a special four-digit code to use the bathrooms in the restaurant and lobby but no such security code is required to enter elevators and access guest room floors. Seriously? Also, in the bar/restaurant, STAFF ASK YOUR ROOM NUMBER IN FRONT OF OTHER GUESTS. This is a huge no-no. Anyone who has ever worked in a hotel knows you aren't supposed to do this. I also received a room with two beds despite traveling alone. Toiletries were low-quality dispensers, and no bar soap was provided. No newspapers, no Choose Chicago magazine, and no local information of any kind. No turndown service. No minibar. Not even a basic snack tray. A robe was provided, but no slippers. Some rooms enjoy fantastic views of State Street and Macy’s; others have none. Amenities like free bikes, coffee, cookies, and a welcome drink (once per stay) are nice gestures but don’t compensate for the lack of basic services—especially since there’s no breakfast of any kind, not even a simple cold buffet. Many lower-end brands with comparable or better operating standards offer free breakfast. The attached restaurant and bar had good food, but service was baffling. They were out of most wines, including the most expensive bottles. The hostess insisted the restaurant was fully booked until 7 p.m. and that only bar seating was available—yet by 5 p.m. the dining room was completely empty. Absurd. Either the reservation system is dysfunctional or they don’t want hotel guests occupying tables. My salmon entrée was above average, but for $35 no bread was served, my water was never refilled, and I wasn’t offered dessert or coffee. All things considered, Staypineapple wants to compete with Kimpton, Royal Sonesta and other four-star boutique brands. While the hotel offers a few thoughtful touches, the operating standard falls well below even a Hampton Inn experience.

Best hotel stay ever I brought my kids and grandkids to Chicago for the tree lighting. When we got to our room with the grandkids the staff had decorated our room for Christmas. They had huge stuffed nutcrackers, small Christmas tree, Christmas lights and cookies and milk for them. It was so nice and very unexpected. The staff was terrific. I will definitely be coming back.

Quirky hotel Great authentic quirky hotel in brilliant location. Beds are super comfy and the staff really friendly. Definitely worth staying here.