Staypineapple, An Iconic Hotel, The Loop is a vibrant blend of historic architecture and playful, modern hospitality set within a landmark Chicago building. Stepping into the lobby, guests are greeted by the grandeur of marble flooring and soaring vaulted ceilings, a nod to the city’s rich design heritage. The experience is uniquely “Staypineapple,” featuring quirky touches like welcome drinks upon arrival and complimentary bicycle rentals for pedaling through the nearby Millennium Park or along the Chicago Riverwalk. The rooms prioritize ultimate relaxation with the brand’s signature “Naked Experience,” which includes exceptionally soft pillowtop beds and premium linens. Located in the heart of the Loop, just minutes from the Art Institute and Michigan Avenue, this dog-friendly hotel offers a soulful and spirited home base for travelers who appreciate both old-world charm and contemporary flair.
