Staypineapple An Iconic Hotel, The Loop
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About this property
Staypineapple An Iconic Hotel, The Loop is a 4-star boutique property located in the heart of Chicago's downtown. Situated a 5-minute walk from both the Chicago Cultural Center and Chicago City Hall, the hotel places guests steps from major attractions including the Chicago Riverwalk (0.4 miles away) and the Art Institute of Chicago (0.5 miles away). The location offers easy access to the city's cultural landmarks and business districts.
The hotel features 122 guestrooms, including 19 suites, each outfitted with pillowtop beds dressed in down comforters and premium bedding. Rooms include iPod docking stations, LCD televisions with cable service, and private bathrooms with shower/tub combinations stocked with designer toiletries and hair dryers. Guests consistently rate room comfort highly at 4.7 out of 5.
Amenities include a fitness center, tour and ticket assistance services, and a ballroom suitable for events. The property offers practical conveniences such as 24-hour front desk service, express check-out, dry cleaning and laundry service, free bicycles, luggage storage, and a safe-deposit box. Complimentary coffee and tea are available in common areas, and free newspapers are provided in the lobby. The hotel maintains multilingual staff and wheelchair-accessible common areas. Valet parking is available for an additional fee.
The property welcomes pets with enthusiasm—dogs stay for $29.95 per night with no size or weight restrictions, and pet-free floors are available for guests with allergies. Check-in runs from 4:00 PM to midnight, and checkout is at 12:00 PM. From Midway Airport, the hotel is approximately 12 miles away (20–30 minutes by taxi or shuttle); from O'Hare, it is 18 miles away (30–45 minutes). The overall guest rating stands at 4.6 out of 5 across more than 1,000 reviews.
Location & nearby attractions
State Street - 0.1 km / 0.1 mi
Daley Plaza - 0.1 km / 0.1 mi
Richard J. Daley Center - 0.2 km / 0.1 mi
Michigan Avenue - 0.3 km / 0.2 mi
CIBC Theatre - 0.3 km / 0.2 mi
Millennium Park - 0.4 km / 0.2 mi
Chicago Cultural Center - 0.4 km / 0.2 mi
Chicago Theatre - 0.4 km / 0.2 mi
Chicago City Hall - 0.4 km / 0.3 mi
Cloud Gate - 0.5 km / 0.3 mi
Cadillac Palace Theatre - 0.5 km / 0.3 mi
Marina City - 0.6 km / 0.4 mi
House of Blues Chicago - 0.6 km / 0.4 mi
Chicago Riverwalk - 0.7 km / 0.4 mi
Harold Washington Library Center - 0.7 km / 0.5 mi
The nearest airports are:
Chicago Midway Airport (MDW) - 18.7 km / 11.6 mi
Chicago O'Hare Intl. Airport (ORD) - 29.4 km / 18.3 mi
Chicago, IL (PWK-Chicago Executive) - 41.8 km / 26 mi
Chicago, IL (DPA-Dupage) - 67.4 km / 41.9 mi
Rockford, IL (RFD-Greater Rockford) - 138.2 km / 85.9 mi
Rooms
Amenities & features
Getting here
Check-in & check-out
- Extra-person charges may apply and vary depending on property policy
- Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
- Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
- Special cancellation policies or charges may apply for group reservations (more than 8 rooms for the same property / stay dates)
- This property accepts credit cards; cash is not accepted
- Cashless transactions are available
- Safety features at this property include a fire extinguisher and a smoke detector
Pet policy
- Pets allowed
- Only dogs are allowed
- Service animals are allowed
- Service animals are exempt from fees/restrictions
- $29.95 pet fee
- per night. We're not just dog friendly
- we're dog obsessed (fee applies). Check out our Pineapple Pup Package for savings! Staypineapple Chicago takes care of all our guests in style—whatever their species. We accept any number of pets without size or weight restrictions. For people with allergies
- we also have pet-free floors.
- Service animals complying with ADA Title lll regulations are allowed.
Fees & policies
You'll be asked to pay the following charges at the property. Fees may include applicable taxes:
- Resort fee: USD 29.29 per accommodation, per night
- Valet parking fee: USD 75 per night
- Pet fee: USD 29.95 per accommodation, per night
- Service animals are exempt from fees<
Know before you go
- Only registered guests are allowed in the guestrooms.
- The property has connecting/adjoining rooms, which are subject to availability and can be requested by contacting the property using the number on the booking confirmation.
- Cashless payment methods are available for all transactions.
- Contactless check-out is available.
- This property welcomes guests of all sexual orientations and gender identities (LGBTQ+ friendly).