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Staypineapple An Iconic Hotel The Loop

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Staypineapple An Iconic Hotel The Loop

locationDowntown, Chicago - IL

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About Staypineapple An Iconic Hotel The LoopAbout Staypineapple An Iconic Hotel The Loop

Location

This boutique hotel is housed within a transformed historic architectural landmark located in the heart of Chicago within a short distance of the Chicago River. The establishment is a short walk from the Millennium Park, Navy Pier and the famous Magnificent Mile. There are many restaurants, bars and shopping venues, as well as links to the public transport network to be found in the surrounding area.

Facility

The hotel was built in 1895. 105 rooms are located on 16 storeys and can be reached by lift. Guests are warmly welcomed by English-speaking staff at the 24-hour reception desk in the lobby. Check-in/check-out service is available round the clock. Amenities include a cloakroom, baggage storage service, safe, currency exchange service and cash machine. Wireless internet access allows guests to stay connected while on holiday. The tour desk offers assistance with booking excursions. The hotel has a range of facilities for guests with disabilities. Wheelchair-accessible facilities are available. There are also a number of shops that make for great strolling and browsing. Additional facilities include a newspaper stand. Guests arriving by car can park their vehicles in the car park. Further services and facilities include room service and a laundry service. Active guests can make use of the bicycle hire service to explore the surrounding area. Complimentary newspapers are available.

Rooms

Air conditioning and individually adjustable heating ensure that rooms maintain comfortable temperatures. All rooms are carpeted and have a double bed, a queen-size bed, a king-size bed or a sofa bed. Extra beds can be requested. A safe, a minibar and a desk are also available. Additional features include a mini fridge and a tea/coffee station. An ironing set is provided for guests' convenience. A direct dial telephone, a television with satellite/cable channels, a radio, a CD player, an alarm clock and WiFi are provided as well. A shower and a bathtub are included the bathrooms. A hairdryer, bathrobes and a telephone are available for daily use. Guests can also book wheelchair-friendly rooms with wheelchair-accessible bathrooms. The hotel has non-smoking rooms.

Sport

The sports and entertainment facilities at the hotel ensure that guests have plenty of activities to choose from during their stay. There are many ways to relax or stay active at the hotel, including cycling/mountain biking, a gym, aerobics and a spa. Parents can unwind while the kids can participate in an entertainment programme full of fun activities.

Meals

Dining facilities include a café and a bar. A number of specialities await guests in the air-conditioned, non-smoking restaurant. A fortifying breakfast is served daily.

Payment

The hotel accepts the following credit cards: American Express, VISA, Diners Club and MasterCard.

Amenities at Staypineapple An Iconic Hotel The Loop Amenities at Staypineapple An Iconic Hotel The Loop

  • Facilities

    • -

      24-hour check-in

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      24-hour reception

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      Air conditioning

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      Bar(s)

    • -

      Bicycle Hire

    • -

      Café

    • -

      Car Park

    • -

      Cloakroom

    • -

      Conference Room

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      Currency Exchange

    • -

      Disability-friendly

    • -

      Foyer

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      Hotel Safe

    • -

      Laundry Service

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      Lifts

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      Newspaper kiosk

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      Pets

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      Restaurant(s)

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      Restaurant(s) with non-smoking area

    • -

      Room Service

    • -

      Shops

    • -

      Wifi

  • Hygiene

    • -

      Contactless check-in/-out

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      Contactless payment

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      Enhanced cleaning programme

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      Hand sanitiser

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      Housekeeping only upon request

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      Hygiene training for staff

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      No high-touch furnishings

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      No high-touch furnishings in public areas

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      Protective hygiene screens

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      Protective masks for guests

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      Sanitiser dispenser

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      Social distancing regulations

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      Use of commercially available disinfectants

  • Sport/Entertainment

    • -

      Aerobics

    • -

      Children's Entertainment

    • -

      Cycling/Mountain Biking

    • -

      Gym

LocationLocation

Map preview

Around this property:

Centre

700 m

Beach

2.5 km

User Rating & ReviewsUser Rating & Reviews

  • Valuerating
  • Roomsrating
  • Cleanlinessrating
  • Servicerating

Excellent

2448

Very Good

650

Average

185

Poor

75

Terrible

57

Recent Reviews: 3415

  • User:Linda N

    Trip type: Couples

    Wonderful!

    rating09 Jun 2026

    Beautiful hotel in a great location. Comfy beds and lots of amenities. Staff was great, especially Sashon B.

  • User:Kimberly B

    Trip type: Family

    Amazing location and cute boutique hotel

    rating07 Jun 2026

    Shocking how much I loved this little boutique hotel!!! My stepdaughter and I spent the weekend exploring Chicago. April in housekeeping and Darnell at the desk couldn’t have been more accommodating and kind! You’ve got a lot of great people but these two made it ultra special. I even saw April out on the street as she was getting to work and she asked how my stay was and if there was anything else she could do to make it special, let her know. Great property with invaluable staff!!! Checkout at noon (rather than the typical 11 am) was ideal and I needed every second of that extra hour. Thank you Staypineapple. I bought a coffee mug and the stuffed puppy dog. Beth Anne King, Owner at Staypineapple, An Iconic Hotel, The Loop Chicago, responded to this review This is AWESOME! Thank you so much for sharing your experience! I will be sure to share your kind words with Darnell and April. They really are GREAT. We are so glad you enjoyed your stay with us in Chicago and truly appreciate you taking the time to share your experience. We hope to host you again soon!Sincerely,Beth Anne KingGeneral Manager

  • User:travelingal60

    Trip type: Business

    Mixed but largely mediocre stay

    rating07 Jun 2026

    I stayed at the Staypineapple for a 2 night business trip and it was just an ok stay. The hotel lobby is very small, taken up primarily by a restaurant which by the way is worth checking out. Check in was smooth and they give you a free drink at check in. The room was a decent size and cutely furnished with a lot of pineapple themed items. Housekeeping was severely lacking as when I pulled back the curtains I noticed a half finished can of soda on the window sill. The next morning I realized the coffee maker was also broken. Also, by the way there is no housekeeping for a 2 night stay unless you request and for all of this they charge a $25 per day resort fee! Room was comfortable enough with a good bed, decent bathroom and quiet noise level. Check out was smooth. Overall a very mixed stay that I will likely not repeat. Beth Anne King, Owner at Staypineapple, An Iconic Hotel, The Loop Chicago, responded to this review Thank you so much for staying with us recently and taking the time to share your experience. We hate to hear that we didn't totally knock this experience out of the park for you. I can certainly understand your disappointment and will be working with my team to ensure we address these issues. We hope you will consider giving us another try on your next trip to Chicago.Sincerely,Beth Anne KingGeneral Manager

  • User:hellomoto88

    Trip type: Family

    Fatastic!

    rating30 May 2026

    We went to Chicago to celebrate my daughter's 30th birthday, and we had a great stay. The hotel location was perfect: around the block from the train station, close to many attractions and restaurants, and tons of retail stores on the same street. The room was very quiet and clean. The front desk was very friendly and helpful. They even left a cute surprise for my daughter. Thanks for a great trip! Beth Anne King, Owner at Staypineapple, An Iconic Hotel, The Loop Chicago, responded to this review Thank you so much for choosing to Staypineapple during such a special trip! I'm thrilled to hear you enjoyed your experience with us! We hope to host you again soon!

  • User:MeganinMSP

    Trip type: Family

    The staff is fantastic!

    rating24 May 2026

    100/100! Another fantastic stay where the staff went above and beyond. We’ve stayed here multiple times and everyone is always so friendly and helpful. They surprised us with some extras this trip and the timing couldn’t have been more perfect given some stressful events the week prior. The new restaurant is great and as always the location can’t be beat. Love staying in a historical hotel and look forward to a return stay late summer. Beth Anne King, Owner at Staypineapple, An Iconic Hotel, The Loop Chicago, responded to this review Thank you so much for staying with us again on your most recent visit to Chicago. We love hosting you! I was thrilled to hear that our treats were so well timed and a needed pick me up. I will be sure to share your kind words with our team. We look forward to seeing you again later this summer! Thank you again for always choosing to Staypineapple!Sincerely,Beth Anne KingGeneral Manager

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