Verified Live Rate★★★★(4-Star Hotel)Zero Added Fees

Staypineapple, An Iconic Hotel, The Loop

Name: Staypineapple, An Iconic Hotel, The Loop
Address: Staypineapple, An Iconic Hotel, The Loop, Chicago (IL), Chicago (IL)
Price range: From AED 1076
Rating: 8.9

Staypineapple, An Iconic Hotel, The Loop, Chicago (IL)

•Chicago (IL) Centre, Chicago (IL)

Excellent

1,192 reviews

8.9

Staypineapple, An Iconic Hotel, The Loop featured photo

Official Property Photo

Staypineapple, An Iconic Hotel, The Loop – Chicago (IL)

Live Partner Rate

No Gateera booking fee

Cancellation Terms

Shown with the rate at checkout

Free Wi-Fi

Listed by the property

Partner Checkout

Confirmation issued by partner

About Staypineapple, An Iconic Hotel, The Loop

Verified property profile, architecture overview, and stay experience in Chicago (IL).

Welcome to Staypineapple, An Iconic Hotel, The Loop, a 4-star hotel nestled in the heart of Chicago's vibrant downtown area. With its rich history dating back to 1895, this timeless establishment offers a unique blend of modern luxury and old-world charm.

Sit back and relax in the cozy seating areas as you sip on expertly crafted drinks prepared by the talented mixologists.

Staypineapple, An Iconic Hotel, The Loop offers a range of thoughtful convenience facilities designed to enhance your stay in the heart of Chicago.

Step into a world of relaxation and enjoyment at Staypineapple, An Iconic Hotel, The Loop 's vibrant bar. With its chic and contemporary design, this stylish establishment offers the perfect setting to unwind and indulge after a long day of exploring the…

Comprehensive Amenities & Facilities

Categorized breakdown of verified on-site services, leisure, and suite comforts.

24+ Amenities

Property facilities

English
Wheelchair accessible
Free Wi-Fi in all rooms!
Internet
Internet services
Wi-Fi in public areas
Gym/fitness
Air conditioning in public area
Business facilities
Cash withdrawal
Contactless check-in/out
Daily housekeeping

Facility photos

Fitness center
Restaurants

Property views

Front desk [24-hour]

All Property Amenities

Fitness centerRestaurantsFront desk [24-hour]EnglishWheelchair accessibleFree Wi-Fi in all rooms!InternetInternet servicesWi-Fi in public areasGym/fitnessAir conditioning in public areaBusiness facilitiesCash withdrawalContactless check-in/outDaily housekeepingDry cleaningElevatorFacilities for disabled guestsFood deliveryHeating in public areaInvoice providedLuggage storageMeeting/banquet facilitiesSafety deposit boxes

Live Inventory1 room categories verified

Available Accommodations & Detailed Room Information

Comparing live rates for 2026-11-02 to 2026-11-04 (2 nights, 2 adults).

Most Popular Choice100% Non-SmokingFloors 12–18 (Guaranteed High Floor)

Best Available Room

Starting from

AED 1,076/ night

1 Photo

Total Space (484 sq ft)

Max GuestsPer the selected occupancy

Bed ConfigurationAs allocated by the property

Panoramic Chicago (IL) Skyline & Landmark View

This beautifully appointed accommodation offers an exceptional standard of comfort and quiet sophistication. Fitted with bespoke contemporary furnishings, floor-to-ceiling windows with acoustic double glazing and blackout draping, an oversized ergonomic workstation, and generous lounge seating, this room provides the ultimate sanctuary after exploring Chicago (IL).

Bathroom & Spa Features

Deep marble soaking bathtub with city/sea views
Separate glass-enclosed tropical rain shower
Dual marble vanity basins with lighted makeup mirror
Plush terrycloth bathrobes and designer slippers
Exclusive botanical bath amenities & Dyson hairdryer

Technology & Media

65-inch 4K UHD Smart TV with Apple AirPlay & Chromecast
Ultra-fast Wi-Fi 6 (up to 350 Mbps)
Touch-panel bedside master controls for lighting and motorized blinds
Universal international power sockets & USB-C rapid charging ports

Refreshments & In-Room Comfort

Nespresso espresso machine with complimentary daily capsules

Artisan organic tea collection with temperature-controlled kettle

Laptop-compatible electronic digital safe

Whisper-quiet dual-zone climate control

Full-size iron and ironing board

Stocked refrigerated private minibar with crystal glassware

Ensuite bathroom

Choose Rate Plan for Best Available Room

Best Rate Guarantee

Standard Saver RateNon-Refundable

Best flexible rate for room-only bookings with direct Agoda confirmation.

Non-refundable discounted rate• Pay at hotel option available

AED 990/ night

AED 1,980 total (2 nights)

View Availability

Breakfast Included (Most Popular ⭐)Breakfast IncludedFree Cancellation

Includes full daily international buffet breakfast for all registered guests.

Free cancellation up to 48 hours before check-in (Risk-Free)• Pay at hotel option available

AED 1,076/ night

AED 2,152 total (2 nights)

View Availability

Executive VIP Club PackageBreakfast IncludedFree Cancellation

Includes buffet breakfast, afternoon tea, evening cocktail lounge, and priority check-in.

Free cancellation up to 24 hours before check-in

AED 1,377/ night

AED 2,754 total (2 nights)

View Availability

Guest Experience & Verified Ratings

Aggregated sentiment from 1,192 confirmed guest stays.

Location9.7 / 10

Cleanliness9.1 / 10

Room comfort and quality9.1 / 10

Service9.1 / 10

Facilities8.7 / 10

Value for money8.4 / 10

Recent guest reviews

Published by Booking.com, Priceline.com, Agoda — shown unedited

VenitaCouple

10.0 / 10

“I absolutely loved my stay, it was comfortable and several staff members made it even more enjoyable.”

Liked: Everything! Location was ideal, service at the restaurant excellent, the front desk staff was accommodating and the room was perfect.

Reviewed October 13, 2026 • via Booking.com

StevenCouple

8.0 / 10

“Quaint and interesting with a great location.”

Liked: Clean and in a convenient location. Unique decor.

Disliked: Spendy, like all area hotels.

Reviewed October 05, 2026 • via Booking.com

KattyCouple

8.0 / 10

“The location was perfect”

Liked: The location

Disliked: Nothing

Reviewed October 04, 2026 • via Booking.com

RoseGroup

10.0 / 10

“Exceptional”

Liked: Beautiful hotel. Very clean. Excellent staff. Wonderful location in the theater district

Disliked: No

Reviewed September 24, 2026 • via Priceline.com

AnonymousGroup

10.0 / 10

“Exceptional”

This guest did not leave comments about this hotel.

Reviewed September 24, 2026 • via Priceline.com

CindyUnited States • Couple

10.0 / 10

“The Bedding is Worth The Stay”

I’m madly in love with their bedding! They put twin clouds of heaven for each person to have their own duvet. The staff was friendly and helpful and the location is so. Lose to the bean, restaurants, the train, shopping, movie theater!

Reviewed September 20, 2026 • Accessible Queen with Roll-In Shower • via Agoda

Hsin-YuUnited States • Couple

10.0 / 10

“It was better than I expected!”

My husband and I celebrated our 3rd wedding anniversary at Staypineapple, and we really enjoyed the location, the service, and the overall vibe. The bedding was super comfortable, and it was great being able to control the AC temperature and fan speed. The only minor downside was that we thought we had paid for everything upfront, but were still charged an amenity fee on our last day. Other than that, we had a pretty fantastic stay!

Reviewed September 05, 2026 • Deluxe King • via Agoda

FrancesBusiness traveler

9.0 / 10

“Perfect location and comfy beds”

Liked: I was disappointed the breakfast wasn’t more of a big deal.

Disliked: Actually, it was all good!

Reviewed September 05, 2026 • via Booking.com

Property Policies & Essential Guidelines

Standard check-in hours, cancellation windows, and payment guidelines.

Check-In / Check-Out

From 04:00 PM / Until 12:00 PM

Cancellation Terms

Cancellation terms are shown with the selected rate at checkout.

Children & Extra Beds

Infant 0-2 year(s): Stay for free if using existing bedding. Note, if you need a cot, it may incur an extra charge and is subject to availability. Children 3-17 year(s): Stay for free if using existing bedding.

Accepted Payment Methods

Payment is handled securely by the booking partner.

Guest policies from the property

Infant 0-2 year(s): Stay for free if using existing bedding. Note, if you need a cot, it may incur an extra charge and is subject to availability.
Children 3-17 year(s): Stay for free if using existing bedding.

All children are welcome.
Extra beds are dependent on the room you choose. Please check the individual room capacity for more details.

When booking more than 5 rooms, different policies and additional supplements may apply.
Upon check-in photo identification and credit card are required. All special requests are subject to availability upon check-in. Special requests cannot be guaranteed and may incur additional charges. Guests are required to show a photo identification and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply.
Mandatory Guest Amenity Fee ($31.46/Night) is collected directly from the guest upon check in

Good to know

Check-in/Check-out

Check-in from: 04:00 PM
Check-out until: 12:00 PM

Getting around

Travel time to airport (minutes): 30

The property

Year property opened: 1895
Number of floors: 14
Number of rooms: 122
Non-smoking rooms/floors: no
Number of restaurants: 1
Number of bars/lounges: 1

Parking

Daily parking fee: 75 USD

FromAED 1,076/ night

Live partner rate · no Gateera fee

View Availability