Make Your Visit Historic

In a city chock full of fabulous—cuisine, art, architecture, and shopping—we proudly present Staypineapple Chicago, An Iconic Hotel. Not to be outdone by the amazing city around it, this award-winning hotel is housed in a National Historic Landmark building and is the perfect jumping-off spot for exploring downtown Chicago. 

Ideally located in the Loop with The Theatre District and Millennium Park just steps away, you are poised to take full advantage of all the city has to offer. Take in the Art Institute of Chicago, shop the glamorous boutiques of the Magnificent Mile, marvel at the details of the Rookery, or cheer along with the crowds at one of the city's many festivals, all before returning to posh accommodations and deluxe amenities. Staypineapple Chicago offers incomparable style, grace, and warmth.