Staypineapple Chicago, An Iconic Hotel, The Loop

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Staypineapple Chicago, An Iconic Hotel, The Loop Staypineapple Chicago is housed in a National Historic Landmark building and is the perfect jumping off spot for exploring downtown Chicago.
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In a city chock full of awesome—cuisine, art, architecture, shopping—we proudly offer Staypineapple Chicago, a historic gem just steps from Millennium Park. Not to be outdone by the amazing city around it, Staypineapple Chicago is housed in a National Historic Landmark building and is the perfect jumping off spot for exploring downtown Chicago. In the Loop and with the Theater District just steps away, you are poised to take full advantage of all the city has to offer. Take in the collections of the Art Institute of Chicago, shop the glam shops and 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 is a bold newcomer with incomparable style, grace and warmth.

New travel buddy unlocked. 🔓🐾 Dash is cute, cuddly and gives back. A portion of his "adoption fee" supports local animal...
10/14/2026

New travel buddy unlocked. 🔓🐾 Dash is cute, cuddly and gives back. A portion of his "adoption fee" supports local animal shelters.

The best nights in Chicago start before you even leave the room. ✨🥂A little ch*****ne, a little getting ready, then out ...
10/12/2026

The best nights in Chicago start before you even leave the room. ✨🥂

A little ch*****ne, a little getting ready, then out the door for dinner, a show or wherever the night takes you.

Enhance your evening with our Something Special add-on and make the getting-ready part feel like part of the night, too.

Dash’s Halloween Costume Contest is officially back for the 10th year! 🎃🐾Think your pup has a costume worth showing off?...
10/09/2026

Dash’s Halloween Costume Contest is officially back for the 10th year! 🎃🐾

Think your pup has a costume worth showing off? Head over to Instagram to enter for a chance to win a two-night Staypineapple stay + swag.

All entries are happening over on on Instagram, so be sure to check out the official contest post for full details and entry instructions.

Enter here: https://f.mtr.cool/mtsjodhvq1

Good luck to all the very well-dressed pups. 💛

Your dog emailed us. They said they neeeeeeed this rn.
10/08/2026

Your dog emailed us. They said they neeeeeeed this rn.

Just five more minutes. And maaaaaaaybe another cup of freshly brewed in bed. ☕
10/05/2026

Just five more minutes. And maaaaaaaybe another cup of freshly brewed in bed. ☕

Chicago is better when the whole family gets to come along. 🏙️🐾🍍
09/26/2026

Chicago is better when the whole family gets to come along. 🏙️🐾🍍

A family trip to Chicago starts with a pretty great home base. 🍍Shebuystravel named Staypineapple Chicago its top pick f...
09/23/2026

A family trip to Chicago starts with a pretty great home base. 🍍

Shebuystravel named Staypineapple Chicago its top pick for families visiting the city, highlighting our spot in the heart of The Loop, historic digs and easy access to some of Chicago’s must-see stops.

Planning a trip with the whole crew? Check out their guide to doing Chicago across generations. 👇

FacebookTweetPinLinkedIn Chicago has figured out something many big cities haven’t: how to give toddlers, school-age kids, parents and grandparents completely different experiences without making the family split up all day....

A huge congratulations to Chefs Rishi Kumar and Zubair Mohajir of Mariela, located inside Staypineapple Chicago, on bein...
09/18/2026

A huge congratulations to Chefs Rishi Kumar and Zubair Mohajir of Mariela, located inside Staypineapple Chicago, on being named among Food & W**e’s Best New Chefs of 2026! 👏

We’re incredibly proud to have such talented chefs creating something special right here in our Chicago hotel.

If you’re visiting Staypineapple Chicago, be sure to add a stop at Mariela to your list. 🍽️

https://www.instagram.com/p/DdUPHozmsRv/?utm_source=ig_web_copy_link&stkn=MzRlODBiNWFlZA==

Some buildings just have stories built in. ✨Staypineapple Chicago calls the Reliance Building home, a Chicago landmark d...
09/16/2026

Some buildings just have stories built in. ✨

Staypineapple Chicago calls the Reliance Building home, a Chicago landmark dating back to 1895 that helped shape the future of skyscraper design.

More than a century later, its ornate ironwork, grand staircases and one-of-a-kind architectural details are still part of the stay.

A pretty incredible backdrop for your next Chicago story. 🍍

Mornings look better in yellow. ☕💛
09/11/2026

Mornings look better in yellow. ☕💛

Address

1 West Washington Street
Chicago, IL
60602

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