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.

Not pictured: the humans who thought this was their hotel room.At Staypineapple Chicago, dogs settle in fast. Cozy beds,...
06/05/2026

Not pictured: the humans who thought this was their hotel room.

At Staypineapple Chicago, dogs settle in fast. Cozy beds, city views, and enough room for the whole pack to feel right at home (even the humans, we guess...). 🐾🍍

Pride season is here, and we’re celebrating in every Staypineapple city. 🌈🍍We’re celebrating all season long with 15% of...
06/03/2026

Pride season is here, and we’re celebrating in every Staypineapple city. 🌈🍍

We’re celebrating all season long with 15% off stays from June 1–August 31 at any Staypineapple hotel when you use code PRIDE when booking.

Now all that’s left? Picking your city, packing your best Pride fit, and getting ready for a summer full of love, community, and unforgettable stories.

📍 Seattle
🧡 Seattle Pride Pride in the Park – June 6
💛 Seattle Pride Parade – June 28

📍 Boston
🧡 Chandler Street Block Party – June 6, right outside Staypineapple Boston
💛 Trophy Room is celebrating all month long with Pride events, sips, music bingo, and more

📍 San Francisco
🧡 San Francisco Pride Celebration – June 27–28
💛 Pride Parade – June 28

📍 New York City
🧡 NYC Pride March – June 28
💛 PrideFest in Greenwich Village – June 28
Proud official hotel partner: Staypineapple New York, An Artful Hotel, Midtown Manhattan

📍 Chicago
🧡 Chicago Pride Fest – June 21–22
💛 Chicago Pride Parade – June 28

📍 Portland
🧡 Pride Northwest Waterfront Festival – July 18–19
💛 Pride Parade – July 19

Book now, celebrate loud, and get ready for a summer where stays become stories. 🏳️‍🌈

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. 🍍

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1 West Washington Street
Chicago, IL
60602

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