** COVID-19 Travel Updates: Learn about our sanitation protocols and flexible cancellation policies. **

Close

First rate comfort & style in the Second City

Staypineapple Chicago

Whether it’s a warm, summer day or a teeth-chattering winter white-out, Staypineapple Chicago will make every day a spectacular one. All of our rooms and suites feature historic touches original to the building while also offering every modern amenity: high-definition TVs, high-speed Wi-Fi and mini fridges. It’s your Windy City oasis.

(Not So) Standard Rooms

View All

Suites

View All

Accessible Rooms

View All