Top-Rated Chicago Escape in the Heart of Stylish Downtown, Chicago, USA

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Stay in the heart of Chicago’s thriving metropolis at the stylish Staypineapple, An Iconic Hotel, The Loop Chicago. Find the brand’s cheeky signature yellow pineapple touches throughout this boutique hotel; from the pineapple-shaped welcome cookies to the emblazoned phone chargers and embroidered pillows. Visit Atwood restaurant and bar and order yourself a signature cocktail before hitting the town, then borrow a beach cruiser bicycle and cycle along the lake or simply spend your time exploring the city on foot.

1 to 31 Nights packages available

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4.7/5

(3K reviews)

Trustpilot

4.8/5

(10K reviews)

Location

Staypineapple, An Iconic Hotel, The Loop Chicago

1 W Washington St, Chicago, IL 60602, United States

Staypineapple, An Iconic Hotel, The Loop Chicago enjoys an ideal location in the heart of Chicago, close to public transport, theatres, Millennium Park and Michigan Avenue shopping. The hotel is located approximately a 25-minute drive from O’Hare International Airport (ORD). Airport transfers are not included in your package, please plan accordingly.

Need flights? Our dedicated flights concierge can assist with all your flight requirements. Contact sales@luxuryescapes.com.

Facilities

Atwood bar and kitchen
Valet parking
Fitness centre
Baggage storage
ATM onsite
Laundry service
Wi-Fi
Check-in: 4pm / Checkout: 12pm

Surcharges may apply to select facilities and services

Fine Print

Package Inclusions: Inclusions are correct at the time of purchase. Refer to your booking confirmation for details. Please note package inclusions for extra guests vary depending on the rate selected, please choose your package carefully.

Dining inclusions do not include beverages (unless otherwise stated). Menus are subject to change without notice.

Please Note: The following applies to select packages only

The included credit must be used during your stay. Any unused credit will be forfeited and cannot be transferred or redeemed for cash.
The resort fee covers: high-speed Wi-Fi, STREAMPINEAPPLE streaming service, in-room tea and coffee, unlimited bottled water and access to the hotel’s beach cruisers.

The property, facilities and dining are subject to government regulations and restrictions. Please check the property website for the most up-to-date information as some of the services may be impacted.

Scoopon reserves the right to modify prices for marketing and commercial reasons. Please note that full terms and conditions apply.

Reviews

9.2

Exceptional

Reviews from Google

Trisha M.

Reviewed 26 Oct 2025

Really enjoyed the uniqueness of this hotel! It’s a classic building with an old elevator but it has so much charm. I loved the pineapple decorations and appreciated that they give you a welcome drink. They also apparently have afternoon pineapple themed treats but I was not around to enjoy. The location couldn’t be better. Shops and restaurants are just around the corner and it’s perfectly situated on the corner in the Loop. I chose not to use their valet parking (to $$) but used SpotHero to find a parking garage right across the street in the Block 37 building.

Recommends this hotel

Laura V.

Reviewed 11 Oct 2025

I want to highlight the kindness of the staff. Especially Mr. Iván, who provided me with emotional support and assistance. During our vacation, my roommate had a serious health problem and had to be hospitalized for several days. The hotel extended my stay without any problems, letting me keep my room until we could return to our home country, Argentina. The entire staff tried to make sure I had a very calm and cared-for stay. Furthermore, the hotel is beautiful, well-maintained, clean, and has an excellent location in the Loop. It's worth noting that it's pet-friendly and pets are welcome. Thank you so much.

Recommends this hotel

SarahBeth C.

Reviewed 12 Sep 2025

We loved this hotel - the vibe was stellar. Loved the trendy, fun, casual vibe combined with the beautiful building and downtown location. Our room was a smidge small, but the view was fantastic, and the bedding was simply out of this world. There's really nothing. more important that comfortable bedding at a hotel, and I'm always surprised when a hotel just doesn't really give it much attention. Stay Pineapple DID give it the attention it deserved and they did well.

Recommends this hotel

Sarah F.

Reviewed 07 Oct 2025

8.0

We really only stayed here because The Burnham Hotel (as it was once called) is a historical hotel. The outside did not disappoint and some of the details inside such as the tile work and wrought iron stairs were beautiful. You can imagine a bit of what it used to be like. In general the staypineapple vibe feels kind of strange in a hotel like that but we did enjoy it overall. The cookies and coffee in the afternoons were nice and we enjoyed the bar. The rooms were ok. Great drapes, but we didn’t love the split comforter on the bed and the bathroom looked like it had seen better days. Specifically the tub tiling and ceiling needed some retouching and the tub itself was rusting. But it’s an old building so you kind of expect that. Service was friendly and attentive. The location you can’t beat. You can walk to so much and the trains are very close. But you’re not too close to the chaos around the riverwalk and the Mag Mile. Would stay here again!

Recommends this hotel

8.0

Reviews: 1-4 of 4

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