Staypineapple Chicago

An Iconic Hotel in The Loop.

Located right at the heart of The Loop in Chicago is the distinctively upbeat boutique hotel, Staypineapple Chicago. In a city full of awesome cuisine, art, architecture, shopping, Staypineapple is minutes from some of the city’s top destinations. Perfect jumping off spot for exploring all the city has to offer.

Chicago’s Loop is named after the shape formed by the elevated train tracks that form its perimeter. It circles Chicago’s downtown and the country’s second largest business district.

NATIONAL HISTORIC LANDMARK

The Staypineapple Chicago is housed in a National Historic Landmark building. It was one of Chicago’s early skyscrapers, originally called Reliance Building. The building was formerly a retail/office space. The infamous dentist, Dr. Frank Brady had a dental office in room 809. One of his customers was the notorious gangster, Al Capone. When Al had a toothache he visited Dr. Frank’s office for treatment and would leave with more for pain relief than just a few aspirin. The dentist served as a “coverup” to some of Capone’s enterprises, besides his professional services. The police discovered this dual practice of Dr. Frank. In addition to providing narcotics, he had also developed an acid that erased the numbers and letters on stolen checks, bonds, and stock certificates.

The building struggled to bring in business during the Great Depression. It was bought off by the City of Chicago and later converted into a luxury hotel, previously known as Hotel Burnham (named after famous Chicago architect and planner Daniel Burnham).