About
About Staypineapple, An Iconic Hotel, The Loop Chicago
A playful Loop stay where rooms, amenities, and personality set the tone.
Staypineapple, An Iconic Hotel, The Loop Chicago brings a more relaxed and design-forward approach to the downtown hotel scene. The interiors combine contemporary styling with lighthearted details, creating an atmosphere that feels less formal than traditional Loop properties. Rooms are arranged with comfort in mind, featuring soft bedding, simple layouts, and thoughtful touches that make short stays feel easy. Amenities such as complimentary bikes, fitness access, and pet-friendly services are woven into the daily experience. The hotel operates with clearly structured policies, ensuring smooth check-ins and consistent service. It’s a stay that leans toward personality and comfort while remaining practical in a central location.
On-site Restaurant & Dining Option
This property has one on-site restaurant: AtwoodExcellent rooms
Front desk [24-hour]
Executive King Suite
396m²This suite features a separate living room with a sofa bed, along with luxury bedding and linens.
Bath or ShowerFlat-screen TV
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Deluxe Double Room
176m²The double room features a tea and coffee maker, a safe deposit box, heating, as well as a flat-screen TV with streaming services. The unit has 2 beds.
Bath or ShowerFlat-screen TV
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Queen Room with Roll-In Shower - Disability Access
176m²The double room offers a flat-screen TV with streaming services, a tea and coffee maker, a safe deposit box and heating. The unit offers 1 bed.
Bath or ShowerFlat-screen TV
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Executive King Suite - Disability Access
396m²This handicap-accessible suite features a separate living room with a sofa bed, along with luxury bedding and linens.
Bath or ShowerFlat-screen TV
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Deluxe King Room
180m²Complete with luxury bedding and linens, this room includes a 50-inch flat-screen HDTV, complimentary bottled water, a small refrigerator and a Keurig coffee maker.
Bath or ShowerFlat-screen TV
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Deluxe Queen Room
176m²This double room features a tea and coffee maker, a safe deposit box and a flat-screen TV with streaming services. The unit offers 1 bed.
Bath or ShowerFlat-screen TV
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Deluxe Double Room
176m²The double room features a tea and coffee maker, a safe deposit box, heating and a flat-screen TV with streaming services. The unit has 2 beds.
Bath or ShowerFlat-screen TV
View Details
Deluxe Queen Room
176m²Complete with luxury bedding and linens, this room includes a 50-inch flat-screen HDTV, complimentary bottled water, a small refrigerator and a Keurig coffee maker.
Bath or ShowerFlat-screen TV
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Millennium Park King Suite
396m²Featuring iconic views of Millennium Park and Lake Michigan, this suite offers a separate living room with a sofa bed.
Bath or ShowerFlat-screen TV
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Deluxe Queen Room with Two Queen Beds
176m²Complete with luxury bedding and linens, this room includes a 50-inch flat-screen HDTV, complimentary bottled water, a small refrigerator and a Keurig coffee maker.
Bath or ShowerFlat-screen TV
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Attractions
Places of Attractions nearby
Explore the best attractions, shopping destinations, and important places near Staypineapple, An Iconic Hotel, The Loop.
Prime Location
In the heart of Chicago
Top Rated
Guest favorite spots
Reliance Building Hotel Burnham
210 ft away
Historical Buildings
Picasso Statue
219 ft away
Monuments and LandmarksReliance Building
Historical Buildings
284 ft away
Macy's Department Store
Other
306 ft away
Macy s on State Street
Famous Streets
307 ft away
International Academy Of Merchandising & Design Ltd
Colleges and Universities
464 ft away
Marshall Field and Company Building
Historical Buildings
493 ft away
Ford Center Theater
Theatres
522 ft away
Ford Center for the Performing Arts Oriental Theatre
Theatres
555 ft away
Sullivan Center
Historical Buildings
622 ft away
Goodman Theatre
Theatres
655 ft away
Staypineapple, An Iconic Hotel, The Loop
Main Facilities
Explore our thoughtfully curated amenities, facilities, and services.
Front desk [24-hour]
Great food & dining
Located in heart of Chicago
Great for activities
Explore Chicago
Where You’ll Be Staying
Planning a stay in Chicago? Get to know the city and explore the best areas to stay.
Discover what each area has to offer and find a hotel in Chicago that suits your trip, budget, and plans.
Located in the Chicago Loop, the hotel sits close to major landmarks, transit options, and business districts.
Nearby Attractions:
- Millennium Park – A short walk away, featuring Cloud Gate and open public space.
- Art Institute of Chicago – One of the city’s leading museums, located nearby.
- State Street Shopping District – A central retail area with shops and restaurants.
- Chicago Theatre District – Historic venues offering performances throughout the year.
- Chicago Riverwalk – A nearby waterfront path with cafés and scenic views.
What to Expect Around Here
The Loop is busiest during the day, driven by offices and tourism. Evenings tend to be quieter compared to other downtown neighborhoods.
Check availability and book Staypineapple The Loop Chicago for a boutique stay with unique amenities in the heart of downtown.
FAQs about
Staypineapple The Loop Chicago
Find answers to common questions about location, policies, amenities, services, and more at Staypineapple, An Iconic Hotel, The Loop. We want to help make your stay comfortable and hassle-free.
What amenities does Staypineapple The Loop Chicago offer?
Staypineapple The Loop Chicago offers bikes, fitness access, Wi-Fi, and pet-friendly services.
Are rooms at Staypineapple The Loop Chicago modern?
Rooms at Staypineapple The Loop Chicago feature modern layouts with boutique design elements.
What is the check-in time at Staypineapple The Loop Chicago?
Check-in at Staypineapple The Loop Chicago typically begins in the afternoon.
What is the check-out time at Staypineapple The Loop Chicago?
Check-out at Staypineapple The Loop Chicago is usually scheduled for late morning.
Does Staypineapple The Loop Chicago allow pets?
Staypineapple The Loop Chicago allows pets under its policies.
Does Staypineapple The Loop Chicago offer Wi-Fi?
Staypineapple The Loop Chicago provides Wi-Fi access in rooms and public areas.
Is Staypineapple The Loop Chicago near Millennium Park?
Staypineapple The Loop Chicago is within walking distance of Millennium Park.
Are there fitness amenities at Staypineapple The Loop Chicago?
Staypineapple The Loop Chicago provides access to fitness facilities.
Do policies at Staypineapple The Loop Chicago require a deposit?
Staypineapple The Loop Chicago generally requires a credit card authorization at check-in.
Is Staypineapple The Loop Chicago suitable for boutique stays?
Staypineapple The Loop Chicago offers a boutique-style experience with unique amenities.
Is Staypineapple The Loop Chicago close to attractions?
Staypineapple The Loop Chicago is near the Art Institute, Riverwalk, and State Street shopping.
Guest Score and Reviews
Loved by Guests, Trusted for Excellence
Guest Score and Reviews
8.8/5
Wonderful
Based on 1352 Reviews
Latest Reviews
View All ReviewsMichelle
May 20, 2026
V. good
Disliked: They use old fashioned keys, so the elevators to guest rooms are unsecured.
Heather
May 18, 2026
Superb
Liked: The staff was super friendly
Disliked: No parking
Josefina
May 18, 2026
Wonderful
Great location, helpful staffand the food at Mariela’s was amazing.
Liked: Clean and helpful staff
Disliked: Na
Robin
May 11, 2026
Superb
Peaceful and convient place to stay.
Liked: I loved the view. The gentleman that checked us in was very nice. The room was quiet. We really liked how well the hotel had been maintained over the years.
Yebandz
May 10, 2026
Good
The stay was good but the staffs was giving me hard time about my stay because the email they sending me wasn’t letting
Liked: It was clean.
Disliked: Some staffs.
Top things to do in Chicago (US)
Popular things to do
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Unstructured tour
Curbside Sedan Transportation from O'Hare or Midway Airport to Downtown Chicago
Activity tour
Friesian Herd Tours, Workshops, Classes and Retreats in the Kettle Moraine area.
nearby Restaurants
Dining and Coffee Spots Close to Staypineapple, An Iconic Hotel, The Loop
you'll find an array of delightful dining and coffee spots to suit every taste. Whether you're in the mood for a quick snack or a leisurely meal, the nearby establishments provide a convenient and enjoyable dining experience during your stay in Staypineapple, An Iconic Hotel, The Loop, you'll find an array of delightful dining and coffee spots to suit every taste. Whether you're in the mood for a quick snack or a leisurely meal, the nearby establishments provide a convenient and enjoyable dining experience during your stay in Chicago.
163 ft away
Atwood
1 W Washington St US
4.2/5
Average rating
0.2 mi away
Miss Ricky's
203 N Wabash Ave US
3.9/5
Average rating
0.2 mi away
LaShuk Street Food
125 S Clark St US
4.6/5
Average rating
0.4 mi away
Land & Lake Kitchen
81 N Upper Wacker Dr US
4.1/5
Average rating
Other