Welcome to

1 W. Washington St.
Chicago, Il 60602

Staypineapple, An Iconic Hotel, is an historic gem that is housed in a National Historic Landmark building and is the perfect jumping off spot for exploring downtown Chicago. 


Get trusted recommendations from  Stay Pineapple’s guest service staff to help you explore the Windy City like a local.

Curated Experiences

Get a selection of curated itineraries from local experts that will help inspire your adventures.

Picasso Sculpture Chicago Point of Interest


Get suggestions from local insiders on businesses and events near Stay Pineapple for you to enjoy during your stay.