Staypineapple Chicago, An Iconic Hotel, The Loop

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.

Your Staypineapple summer starter pack is waiting. All you have to do is book it 🍍
05/29/2026

Your Staypineapple summer starter pack is waiting. All you have to do is book it 🍍

The more you stay, the less you pay 🍍 This summer, CORE members get to choose their own adventure: stay 3 nights and sav...
05/13/2026

The more you stay, the less you pay 🍍 This summer, CORE members get to choose their own adventure: stay 3 nights and save 50% on your third, or go for 4 and your fourth night is on us. Use code JUICY when booking to unlock this exclusive offer: https://f.mtr.cool/vvjwqrncga

Summer in Chicago hits different and we have a front row seat to all of it. ☀️Wrigley Field, Millennium Park, the Theate...
05/06/2026

Summer in Chicago hits different and we have a front row seat to all of it. ☀️

Wrigley Field, Millennium Park, the Theater District — it's all close. And right now, stay three nights and get the fourth on us with code FREE when booking directly.

Plan your summer trip: https://f.mtr.cool/bmcfxlkhxm

An apple a day is fine. But a pineapple cookie (or a few...) from Afternoon Delights is better. 🍍
04/26/2026

An apple a day is fine. But a pineapple cookie (or a few...) from Afternoon Delights is better. 🍍

Happy Earth Day from the Windy City 💚🏙️Chicago, you already know about our Green Key Certification, but today feels like...
04/22/2026

Happy Earth Day from the Windy City 💚🏙️

Chicago, you already know about our Green Key Certification, but today feels like the perfect day to celebrate it. We're proud to be recognized for our commitment to eco-friendly operations, and we're just getting started.

Read the full Earth Day blog to see everything we're doing across Staypineapple to make every stay a little greener:

Earth Day is kind of a big deal around here — and not just for one day. At Staypineapple, we’re all about making thoughtful choices that are good for you and the planet.

Tax season is rough, so we're covering your hotel taxes. 💸 For 72 hours only, all room & amenity fee taxes are on us at ...
04/15/2026

Tax season is rough, so we're covering your hotel taxes. 💸 For 72 hours only, all room & amenity fee taxes are on us at every Staypineapple property. Book by April 17 with code TAXDAY and stay anytime through December 30. Book here: https://f.mtr.cool/evyviruysk

We do not speak before coffee. Hotel paw-licy. 🍍☕
04/08/2026

We do not speak before coffee. Hotel paw-licy. 🍍☕

Pineapple cookies and coffee are great. Pineapple cookies and coffee in bed? Even better. 🍍
04/02/2026

Pineapple cookies and coffee are great. Pineapple cookies and coffee in bed? Even better. 🍍

Your Staypineapple story could be your next stay 🍍✨We just launched Where Stories Become Stays — our new Instagram conte...
04/02/2026

Your Staypineapple story could be your next stay 🍍✨

We just launched Where Stories Become Stays — our new Instagram contest celebrating real guest moments (aka yours).

Want in? 👀

Head to our Instagram, check our pinned post to see how to enter + start sharing. https://f.mtr.cool/hbqjipkcsc

🔗 Get the details: https://f.mtr.cool/ltwaefbsna

04/01/2026

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1 West Washington Street
Chicago, IL
60602

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