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Staypineapple, An Iconic Hotel, The Loop

★★★★·9.4/ 10Excellent
·Hotels
1895 opened· 122 rooms· Check-in 04:00 PM / out 12:00 PM
Fitness facilities (surcharge)Air conditioningLift / ElevatorLuggage storageFacilities for disabled guestsParkingAll 38 facilities +
Review
Official

Great care is taken to ensure guests experience comfort through top-notch services and amenities. Remain linked during your visit by utilizing the complimentary internet access available. Experience the wonders of Chicago (IL) with ease by utilizing the services provided at taxi. Parking is accessible, supplied by the hotel for guests who arrive by car. Effortlessly plan your daily activities and travel requirements with express check-in or check-out, luggage storage and safety deposit boxes provided by the front desk services. For extended visits or whenever required, the dry cleaning service and laundry service ensures your preferred travel garments remain clean and accessible. Need some relaxation? Your room features daily housekeeping to make your stay even more comfortable and enjoyable. The hotel is completely smoke-free. Crafted for coziness, every guestroom provides an array of features, guaranteeing a tranquil night's sleep while maintaining the level of comfort. For a more enjoyable stay, select rooms at hotel are equipped with blackout curtains and air conditioning. For certain chosen rooms, guests can enjoy in-room amusement like television, in-room video streaming and cable TV as a part of their stay. Rest assured that your hydration needs will be met, as some guestrooms are equipped with a refrigerator, bottled water, a coffee or tea maker and mini bar. Maintain your cleanliness and comfort using a hair dryer, toiletries and bathrobes available in select guest restrooms. Indulge in the numerous pursuits available at Staypineapple, An Iconic Hotel, The Loop. Eliminate those holiday calories by stopping by hotel and making use of their well-equipped exercise amenities.

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Guest scores & sentiment

From 537 guest reviews · multi-source · as of 2026-07-05

Guests praise the prime location, historic charm, and friendly staff, along with pineapple-themed touches. Common complaints include small rooms, outdated fixtures, poor soundproofing, and unexpected daily amenity charges.

Dimension scores · cross-source

Location9.8
Cleanliness9.6
Service9.2
Value8.8
Facilities8.8
Surroundings8.8
PraisedPrime location · Attentive service · Vintage charm · Comfortable beds
ComplaintsSmall rooms · Extra fees · Limited amenities · Isolated service/hygiene issues

KEYIdeal for location-focused travelers. Expect small rooms, check for extra fees, and be mindful of noise levels.

FAQ · grounded in hotel data & reviews

locationIs the location convenient? What attractions are nearby?
With a location score of 9.8, it is in the heart of the Loop, walking distance to Michigan Avenue and Millennium Park.
pros_consWhat are the main pros and cons according to guests?
99% recommendation rate. Pros: great location, friendly staff, pineapple theme. Cons: small rooms, poor soundproofing, and hidden daily fees.
roomHow are the room facilities? Suitable for business?
Rooms have vintage decor and comfy beds, but business guests note small workspaces and insufficient outlets. Some report outdated fixtures and noise issues.
policyWhat are check-in/out times? Are pets allowed?
Check-in is at 16:00 and check-out at 12:00. Pets are allowed with provided bowls and baskets. Accessible rooms and elevators are available.
diningHow is the dining? What about the costs?
The hotel has a restaurant and offers welcome drinks. However, dining options are limited, and WiFi/dining services are noted as expensive.
familyIs this hotel suitable for families? Any notes?
Suitable for families, but rooms can be tight with smaller beds. Lack of microwaves and extra facility fees are common concerns.
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