Staypineapple, An Iconic Hotel, The Loop

4.4

Excellent(1,241 Reviews)

Hotel in Chicago, IL

4-Star Hotel

Reasons to book

Great for petsBring all your friends and family, even the furry ones

Includes essentialsPets allowed, Kitchen or Kitchenette, Air conditioner and more

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this hotel

Historic Chicago architecture, designed by world renowned architect Daniel Burnham, with mosaic floors and marble ceilings inspire luxury at this hotel in Chicago’s Loop. Shopping on famed Michigan Avenue and Millennium Park are a short walk away.

Amenities

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

Parking

Wheelchair accessible

Gym or Fitness Center

Map of Chicago, IL

Nearby attractions

Museum of Science and Industry, Chicago

11 mi

Available Rooms

1 King • 182 ft²

Sleeps 2

You'll be directed to Booking.com for availability & pricing

1 Queen • 172 ft²

Sleeps 2

You'll be directed to Booking.com for availability & pricing

1 King • 398 ft²

Sleeps 4

You'll be directed to Booking.com for availability & pricing

1 King • 398 ft²

Sleeps 4

You'll be directed to Booking.com for availability & pricing

1 King • 398 ft²

Sleeps 4

You'll be directed to Booking.com for availability & pricing

$$$$

Staypineapple, An Iconic Hotel, The Loop

$$$$

4.4

Excellent(1,241 Reviews)

Hotel in Chicago, IL

4-Star Hotel

Reasons to book

Great for petsBring all your friends and family, even the furry ones

Includes essentialsPets allowed, Kitchen or Kitchenette, Air conditioner and more

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this hotel

Amenities

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

Parking

Wheelchair accessible

Gym or Fitness Center

Map of Chicago, IL

Nearby attractions

Museum of Science and Industry, Chicago

11 mi

Available Rooms

1 King • 182 ft²

Sleeps 2

You'll be directed to Booking.com for availability & pricing

1 Queen • 172 ft²

Sleeps 2

You'll be directed to Booking.com for availability & pricing

1 King • 398 ft²

Sleeps 4

You'll be directed to Booking.com for availability & pricing

1 King • 398 ft²

Sleeps 4

You'll be directed to Booking.com for availability & pricing

1 King • 398 ft²

Sleeps 4

You'll be directed to Booking.com for availability & pricing

Reviews

4.4

Excellent(1,241 Reviews)

100% verified reviews

4.4

Sep 2024

Central Location.

Very friendly staff. Ideal central location. Good facilities.

Nothing

4.4

Mar 2024

Hotel viejo y con limitados servicios

La ubicación del hotel

Hotel viejo, baños poco actualizados, no cuenta con limpieza todos los días.

4.4

Mar 2024

Excelente localização

Me cobraram um valor diferente do que o que estava aqui no booking. Funcionários da recepção são bem enrolados, mas os demais são muito solícitos e educados. Localização EXCELENTE!

Me cobraram um preço diferente do que eu tinha no booking (alegaram ser taxa, mas ficou um tanto diferente) e os funcionários da recepção são bem enrolados. Eu estava com muita pressa no check out e não quis argumentar muito.

4.4

Nov 2023

Chicago in einem historischen Hotel(gebäude)

Die Lage war ausgezeichnet, direkt am Loop, alles in Gehweite, Zugang zur Ubahn/Hochbahn. Hotel ist in einem historischen Gebäude! Zimmer waren alt und sehr schön, alles vorhanden was man braucht, grosse Fenster, sauberes Badezimmer, grosses und bequemes Bett. Fantastische Stiegen (Architektur)

Mir fällt nichts ein, eventuell Frühstück schon ab 6 Uhr morgens, statt ab 7 Uhr (Jetlag)

4.4

Aug 2023

Stayed here for a quick weekend trip. Loved the location and close to shopping

Loved the location

Nothing

4.4

Aug 2023

Average stay

Modern property with old charm. Rooms can get quite noise due to the street but nothing unmanageable and the view makes up for it. Really good location and charming building.

Service was average. We’ve waited 10min before being seated (or acknowledged) for breakfast even though it wasn’t busy. When asked for late check out (we were willing to pay for it) and we were advised to call back in the morning at 7am as it is based on a ‚first in - first served‘ basis. After setting our alarm and calling at exactly 7am we were then told it wouldn’t be available on the day. We were looking forward to our stay considering the pineapple theme and charm however left underwhelmed. Have previously stayed in a StayPineapple in San Francisco and there are worlds between these two hotels.

4.4

Aug 2023

Welcoming hotel with staff that makes you feel like family and beds that make you never want to leave!

The charm of the historic building was welcoming - as were all the little pineapple touches!

Nothing - everything was beautifully detailed and well cared for.

4.4

Aug 2023

First time to Staypineapple and will definitely stay again.

The location was great. Staypineapple is a couple blocks from Millennium Park in one direction and a few blocks from the Riverwalk in another. The beds were so comfy! The bathroom was good size with a tub/shower. I loved the "how to use the duvet" instructions and it just made for a great night sleep. The front desk staff were excellent, knowledgeable and helpful. The Pineapple water in the lobby was a nice feature so we could fill our bottles as we went out for the day touring. I would stay here again without question.

There wasn't any conditioner in the shower and I would've called but I was leaving that day. Otherwise everything was great!

4.4

Aug 2023

Very good

Need more than 1 Valet

4.4

Jul 2023

Convenient but old.

Location is great, nearby the hub and lots of stations, and the receptionist is very helpful.

Facilities are pretty old… you can tell it very obviously from everywhere. The bathroom is not in a good shape as well, and there are problems with their toilets and bathtub’s faucet.

4.4

Jul 2023

Very good

Convenient location and free bike rental

No breakfast

4.4

Jul 2023

Weekend in Chicago

The location is a must in the centre of Chicago and close to everything you need. The staff was very helpful.

Our mattress cover had a stain on it and for the price we paid that can't happen.

4.4

May 2023

Fun getaway in a cool hotel

good location, clean, & great service

bar & restaurant closed at 10pm

4.4

Apr 2023

it was nice and welcoming with a good area, will be my go to hotel from now on!

Area/very cozy environment with nice employees!

none

4.4

Apr 2023

Beautiful hotel, helpful staff and great location

Beautiful hotel

Size of the rooms

4.4

Apr 2023

The Staypineapple offers a classic Chicago experience with a modern pineapple-themed flair in a convenient location.

I loved the historic building, and all the pineapple-themed touches are adorable. The location is great—easy walk to everywhere we went. And I appreciated the free drink at the restaurant.

The $70 to park our car seemed steep but may be standard.

4.4

Apr 2023

Good for a night.

Location. Beds and the pillow I used were very comfy. Complentary beverage at the bar was nice. The fact that the hotel is in a historically significant building that survived the Great Fire is really cool. Even being next to an elevator, the room was super quiet.

Hot water in shower was very loud and sounded awful. Wasn't hot enough either. Tub didn't drain after running the bath water to get it hot. Pictures look better than reality.

4.4

Apr 2023

Fantastic Hotel with an Incredible Staff.

The hotel is perfectly located to all the things that we had planned for our first time visiting Chicago. The staff (Jack, Sashon, Alex, William, & Brandon) were incredible, accommodating, friendly, and genuine. The rooms were so comfortable and clean. As a former Director of Ops in a NYC hotel, I was so impressed.

There is not one bad thing to say about this hotel.

4.4

Mar 2023

Great location, good value, European vibe. Small suite for the price of a tiny room at **** hotels nearby. Super dog-fri

location, staff, handy bar-restaurant with nice light and vibe, terrific dog-policy

Although in a storied historic building, the renovation is slightly rough around the edges; not a gut-Reno, but still nice on-balance. As is becoming common, not much service, no doorman to help with luggage, housekeeping not daily. Given the price, this was OK.

4.4

Mar 2023

I came up for Christmas. I enjoyed my stay.

The location

there was a lot of wear and tear around the baseboards in the ceiling

4.4

Mar 2023

Excellent stay, new fav in Chicago

Excellent location in Chicago! the hotel is beautiful, they have taken “it’s the little things” very seriously. our view was great too. the attached restaurant has very good food too but make reservations. we also used valet parking, easy!

They have enormous windows and drapes but they are not totally blackout. City light can still peek In.

4.4

Jan 2023

I must definitely come back.

I love this place, very clean and the staff very friendly!!

you need a reservation for breakfast on Saturday.

4.4

Jan 2023

Above and Beyond

The building was amazing, the elevators and doors. I loved everything and the views were out of this world! The staff was amazing, check-in was seamless, I asked for a late checkout b/c of zoom meetings and it was granted. My husband left his watch charger so we contacted the hotel, everyone was very helpful and shipped it back to us. This place is amazing and so are the people, I highly recommend staying. We’ll be back!

Nothing!

FAQs

How much does this hotel cost compared to others in Chicago?

The average price for a rental in Chicago is $260 per night. This rental is $99 less expensive than the average.

Is parking included with this hotel?

Yes, parking is listed as an amenity at Staypineapple, An Iconic Hotel, The Loop. For more information, we encourage you to contact the property about where to park.

Is there a pool at this hotel?

We didn’t find pool listed as an amenity for this hotel. It may be worth double checking if a pool is important for your stay.

Is Staypineapple, An Iconic Hotel, The Loop pet friendly?

Yes! This hotel is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Staypineapple, An Iconic Hotel, The Loop?

We found 8 amenities for this rental. This includes air conditioner, pets allowed, kitchen or kitchenette, internet / wifi, and parking.

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4.1

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The Drake Hotel

Staypineapple, An Iconic Hotel, The Loop

Hotel in Chicago, IL

Reasons to book

About this hotel

Amenities

Map of Chicago, IL

Nearby attractions

Available Rooms

Staypineapple, An Iconic Hotel, The Loop

Hotel in Chicago, IL

Reasons to book

About this hotel

Amenities

Map of Chicago, IL

Nearby attractions

Available Rooms

Reviews

FAQs

How much does this hotel cost compared to others in Chicago?

Is parking included with this hotel?

Is there a pool at this hotel?

Is Staypineapple, An Iconic Hotel, The Loop pet friendly?

What amenities are available at Staypineapple, An Iconic Hotel, The Loop?

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