NOTICE: Our booking engine will be down for maintenance from 1 AM PDT to 1 PM PDT today. Please call us at (866) 866-7977 to make a reservation.


A Hotel for Huskies just minutes from UW campus. Check out our serious style, colorful motif, and a range of upscale amenities.

Staypineapple Chicago exterior at night
An Iconic Hotel
Chicago The Loop
Map Attractions 1 W. Washington Street
Chicago, IL, 60602
(312) 940-7997

Fall “In Sleep” With Us

Best Rate Guaranteed
View or modify a reservation

Make Your Visit Historic

Staypineapple Chicago

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.




Don't miss out on our special offers for your summer trip!


3rd Night Free

One. Two. Free! Stay 2 nights and get the 3rd night free. You deserve it!

Book Now

What's nearby