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.

International Dog Day calls for a very important team announcement. 🐾🍍Paws on Payroll is officially HERE!Meet Goofy, Geo...
08/26/2026

International Dog Day calls for a very important team announcement. 🐾🍍

Paws on Payroll is officially HERE!

Meet Goofy, Georgia, Gucci and Harper, the Staypineapple pups bringing tail wags, lobby welcomes, security checks, zoomies and plenty of personality to the job.

They’ve got titles. They’ve got responsibilities. They’ve definitely got opinions.

Swipe to meet the team!💚

Bark Week is officially here. 🐶🍍From August 24–30, we’re celebrating the pups who make stays better while giving back to...
08/25/2026

Bark Week is officially here. 🐶🍍

From August 24–30, we’re celebrating the pups who make stays better while giving back to Seattle Humane. Here’s how you can join in:

🐾 Book a pet-friendly stay this week and we’ll donate the pet fee to Seattle Humane

💚 Donate directly to Seattle Humane: https://f.mtr.cool/08gvgsxhtz

🥫 Drop off unopened pet food or treats at any of our Seattle hotels for the Seattle Humane Pet Food Bank and receive a Staypineapple x Toby & Linus toy with a qualifying donation, while supplies last.

📸 Join us for Bark to School at The Maxwell Hotel on August 29: https://f.mtr.cool/4xj30xkt51

However you choose to join us, it all helps support Seattle Humane. 💛 Swipe through for the details!

08/21/2026

We planned a trip to Chicago last weekend and stayed at the best dog-friendly hotel.

Would your dog love this hotel setup?

Staypineapple Hotels

Staypineapple: for kids, adults, pets, and anyone who believes hotel stays should be a little more fun. Life is too shor...
07/21/2026

Staypineapple: for kids, adults, pets, and anyone who believes hotel stays should be a little more fun. Life is too short for boring hotel stays!!

No matter what you're celebrating, do it the Staypineapple Chicago way (with a view of the The Chicago Theatre and with ...
07/20/2026

No matter what you're celebrating, do it the Staypineapple Chicago way (with a view of the The Chicago Theatre and with the Something Special upgrade) 🥂

Captured a Staypineapple moment during your stay? Don’t let it live in your camera roll forever. 🍍Share it on Instagram ...
07/15/2026

Captured a Staypineapple moment during your stay? Don’t let it live in your camera roll forever. 🍍

Share it on Instagram for your chance to come back for a complimentary two-night stay.

Here’s how to enter:
1. SNAP + SHARE your recent Staypineapple moment on Instagram as an new in-feed post or Reel
2. TAG
3. DM us the word “STORY”

Each month, one guest wins a complimentary two-night stay, plus you may be spotlighted on our page.

Share your story. It might just earn a sequel.

Full details + Official Rules: https://f.mtr.cool/bsxtvkwtzf

OOO until further notice (or until checkout, whichever comes later)
07/14/2026

OOO until further notice (or until checkout, whichever comes later)

Staypineapple Chicago has been nominated for 'Best Boutique Hotel' in 10BEST Awards, and after placing third last year,...
07/08/2026

Staypineapple Chicago has been nominated for 'Best Boutique Hotel' in 10BEST Awards, and after placing third last year, we’re hoping to make this year even sweeter.

This nomination means a lot to our team, our guests, and everyone who’s made Staypineapple part of their travel story.

Voting is open now through August 3, and you can vote once DAILY, per device.

Visit https://f.mtr.cool/vwcpetxxgl to vote. Thank you for the pineapple love. 💛

Red, white, and booked. 🇺🇸Our 4th of July Flash Sale is here with 25% OFF stays through May 31, 2027.Book now through 7/...
07/03/2026

Red, white, and booked. 🇺🇸

Our 4th of July Flash Sale is here with 25% OFF stays through May 31, 2027.

Book now through 7/6 and give your future self something to look forward to.

Book here: https://f.mtr.cool/mccvbkntos

TODAY IS THE DAY 🍍For International Pineapple Day, we’re dropping our biggest promo ever: 99% OFF.Yes, that means select...
06/27/2026

TODAY IS THE DAY 🍍

For International Pineapple Day, we’re dropping our biggest promo ever: 99% OFF.
Yes, that means select rooms will be around $1–$2 before taxes and fees. Yes, it’s real. Yes, we’re freaking out a little.

The drop goes live today at 12pm PT. Limited rooms, while supplies last: https://f.mtr.cool/jpkghsxzvw

(refresh the linked page at 12pm PT to unlock the secret ‘BOOK THIS DEAL’ button)
and if you miss the 99% off drop, don’t panic. amenity fees are waived all day long (using the secret ‘BOOK THIS DEAL’ button, because International Pineapple Day is still International Pineapple Day.

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1 West Washington Street
Chicago, IL
60602

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