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8.8

1,129 reviews

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

1 W. Washington Street, Chicago, 60601, Illinois, United States

Reservations:

+1 (888) 385-6828
, 

Choose dates to view prices

Restaurant

Free wifi

Fitness center

Streaming service (like Netflix)

Air conditioning

Bar

24-hour front desk

Non-smoking rooms

Staypineapple, An Iconic Hotel, The Loop

Welcome to Staypineapple, An Iconic Hotel, located in the vibrant city of Chicago, Illinois. This 4-star hotel is situated in The Loop, just 4.1 kilometers from the city center. With 1129 rave reviews, you can trust that your stay here will be nothing short of exceptional.

Starting at just $106, Staypineapple offers a range of amenities to make your stay comfortable and enjoyable. The hotel is pet-friendly, so you can bring your furry friend along for an extra charge. You'll also have access to private parking, free WiFi, and a 24-hour front desk for any of your needs. The hotel features a bar and restaurant, perfect for relaxing and indulging in delicious meals and refreshing drinks. Staypineapple also offers a free fitness center, so you can stay active during your stay.

The rooms at Staypineapple are thoughtfully designed and equipped with all the essentials. With air conditioning, free toiletries, a bathtub, and a flat-screen TV, you'll have everything you need for a comfortable stay. The hotel is also wheelchair accessible, ensuring that all guests can enjoy their stay. Daily housekeeping is provided, and additional amenities such as bicycle rental and dry cleaning are available for an extra charge.

Enjoy a delightful stay at Staypineapple, An Iconic Hotel, and experience true comfort and convenience in the heart of The Loop. Book your stay today!

When it comes to dining options, Staypineapple has you covered with their on-site restaurant, Atwood. This modern restaurant offers a delightful dining experience with its American cuisine. Whether you're in the mood for a hearty breakfast, a satisfying lunch, or a delicious dinner, Atwood has something to satisfy every palate. With its convenient location within the hotel, you can enjoy a scrumptious meal without even stepping foot outside.

At Staypineapple, you have a variety of payment options to choose from. Cash is not accepted, but you can easily pay with Discover, Mastercard, Diners Club, Visa, American Express, or UnionPay. This flexibility makes it convenient for you to settle your bill and enjoy a hassle-free stay.

Now, let's talk about the room types available at Staypineapple. From the cozy Deluxe Double Room to the spacious Executive King Suite, there's a room to suit every traveler's needs. The rooms are beautifully designed and equipped with essential amenities such as air conditioning, free toiletries, a bathtub, and a flat-screen TV. Plus, with daily housekeeping, you can always expect a clean and comfortable space to return to after a day of exploring the city.

Come and experience true comfort and convenience at Staypineapple, An Iconic Hotel. Whether you're traveling with a pet, enjoying a delicious meal at Atwood, or settling in for a restful night in one of their thoughtfully designed rooms, your stay at Staypineapple will be one to remember. Book your stay today and get ready to indulge in the best that The Loop has to offer!

Closest airports

Chicago Midway International Airport

9mi

Chicago O'Hare International Airport

15.7mi

Most popular amenities

Restaurant

Free wifi

Fitness center

Streaming service (like Netflix)

Air conditioning

Bar

24-hour front desk

Non-smoking rooms

Wheelchair accessible

Elevator

Rooms

Millennium Park King Suite in Staypineapple, An Iconic Hotel, The Loop
Millennium Park King Suite in Staypineapple, An Iconic Hotel, The Loop
Millennium Park King Suite in Staypineapple, An Iconic Hotel, The Loop
Millennium Park King Suite in Staypineapple, An Iconic Hotel, The Loop
Millennium Park King Suite in Staypineapple, An Iconic Hotel, The Loop
Millennium Park King Suite in Staypineapple, An Iconic Hotel, The Loop
Millennium Park King Suite in Staypineapple, An Iconic Hotel, The Loop
Millennium Park King Suite in Staypineapple, An Iconic Hotel, The Loop
Millennium Park King Suite in Staypineapple, An Iconic Hotel, The Loop
Millennium Park King Suite in Staypineapple, An Iconic Hotel, The Loop
Millennium Park King Suite in Staypineapple, An Iconic Hotel, The Loop
Millennium Park King Suite in Staypineapple, An Iconic Hotel, The Loop
Millennium Park King Suite in Staypineapple, An Iconic Hotel, The Loop
Millennium Park King Suite in Staypineapple, An Iconic Hotel, The Loop
Millennium Park King Suite in Staypineapple, An Iconic Hotel, The Loop
Millennium Park King Suite in Staypineapple, An Iconic Hotel, The Loop
Millennium Park King Suite in Staypineapple, An Iconic Hotel, The Loop
Millennium Park King Suite in Staypineapple, An Iconic Hotel, The Loop

Show 6 photos

Millennium Suite, Park View

1 King Size Bed

395 sqft

Flat-screen TV

Streaming service (like Netflix)

Refrigerator

Tea/Coffee maker

+

More details

Welcome to our Millennium Park King Suite, a spacious 398 sqft suite designed to accommodate 4 adults and 3 children comfortably. Unwind in the sitting area or enjoy the modern amenities such as the flat-screen TV, coffee machine, and refrigerator. With a luxurious king-size bed and a range of other comforts, your stay with us is bound to be memorable.

Deluxe Double Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Double Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Double Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Double Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Double Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Double Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Double Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Double Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Double Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Double Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Double Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Double Room in Staypineapple, An Iconic Hotel, The Loop

Show 4 photos

Deluxe, 2 Queen Size Beds

2 Double Beds

175 sqft

Flat-screen TV

Streaming service (like Netflix)

Refrigerator

Tea/Coffee maker

+

More details

Indulge in the spacious tranquility of our Deluxe Double Room, offering 172 sqft of elegant comfort. Relax with your loved ones as this room accommodates 4 adults and 3 children. Enjoy your favorite shows on a flat-screen TV, unwind in a relaxing bathtub, and start your day off right with a freshly brewed cup of coffee from the in-room coffee machine.

Show 6 photos

Millennium Suite

1 King Size Bed

Free wifi

Flat-screen TV

Refrigerator

Tea/Coffee maker

+

More details

Executive King Suite - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite - Disability Access in Staypineapple, An Iconic Hotel, The Loop

Show 5 photos

Executive Suite, Accessible

1 King Size Bed

1 Sofa Bed

395 sqft

Flat-screen TV

Streaming service (like Netflix)

Refrigerator

Tea/Coffee maker

x8

+

x5

More details

Executive King Suite in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite in Staypineapple, An Iconic Hotel, The Loop
Executive King Suite in Staypineapple, An Iconic Hotel, The Loop

Show 5 photos

Executive Suite

1 King Size Bed

395 sqft

Flat-screen TV

Streaming service (like Netflix)

Refrigerator

Tea/Coffee maker

+

More details

Show 4 photos

Atwood, Queen Size

1 Queen Size Bed

Pet Friendly

Non-smoking rooms

Wheelchair accessible

+

More details

Queen Room with Roll-In Shower - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Queen Room with Roll-In Shower - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Queen Room with Roll-In Shower - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Queen Room with Roll-In Shower - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Queen Room with Roll-In Shower - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Queen Room with Roll-In Shower - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Queen Room with Roll-In Shower - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Queen Room with Roll-In Shower - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Queen Room with Roll-In Shower - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Queen Room with Roll-In Shower - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Queen Room with Roll-In Shower - Disability Access in Staypineapple, An Iconic Hotel, The Loop
Queen Room with Roll-In Shower - Disability Access in Staypineapple, An Iconic Hotel, The Loop

Show 4 photos

Queen Room, Accessible

1 Queen Size Bed

170 sqft

Flat-screen TV

Streaming service (like Netflix)

Refrigerator

Tea/Coffee maker

x4

+

x3

More details

Show 4 photos

Deluxe, Queen Size, Accessible

1 Queen Size Bed

175 sqft

Wheelchair accessible

+

More details

Deluxe King Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe King Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe King Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe King Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe King Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe King Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe King Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe King Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe King Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe King Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe King Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe King Room in Staypineapple, An Iconic Hotel, The Loop

Show 4 photos

Deluxe, King Size

1 King Size Bed

180 sqft

Flat-screen TV

Streaming service (like Netflix)

Refrigerator

Tea/Coffee maker

x4

+

x3

More details

Deluxe Queen Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Queen Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Queen Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Queen Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Queen Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Queen Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Queen Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Queen Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Queen Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Queen Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Queen Room in Staypineapple, An Iconic Hotel, The Loop
Deluxe Queen Room in Staypineapple, An Iconic Hotel, The Loop

Show 4 photos

Deluxe, Queen Size

1 Queen Size Bed

175 sqft

Flat-screen TV

Streaming service (like Netflix)

Refrigerator

Tea/Coffee maker

x4

+

x3

More details

Show 4 photos

Deluxe, 2 Double Beds, Accessible

2 Double Beds

Wifi

More details

Deluxe Suite

1 King Size Bed

375 sqft

Free wifi

Minibar

Flat-screen TV

+

More details

Guest reviews

8.8

1,129 reviews

Categories of assessments

Cleanliness

Comfort

Location

Facilities

Staff

Value for money

WiFi quality

Featured reviews:

🇺🇸

Carol

10

July 2024

Very interesting old building. Had been renovated in a way that effectively mixed the old structure and materials with new. The staff was excellent. They helped us so much. Location was fantastic.

Room was very small. Too many pillows and nowhere to put them. No place to put luggage to unpack. Price was high (but so were all prices in Chicago). Didn't like $50 per day charge for WiFi, water bar+metal water bottle, borrowing bicycles, and a couple of other optional items. Those should either have been free or charged only if used.

🇺🇸

Robert

8.2

May 2025

Location was excellent. Hotel was beautifully renovated to honor the historic nature of the building. Large windows with great a view down State Street to the Marshal Field building and Chicago Theater.

The price was way more than we have ever spent in fifty plus years of international travel. Our “deluxe” king room was very small as was the bathroom. I felt the $24.95 Daily Amenity Charge (for a coffee maker, 1 bottle of water and a welcome drink) that was sprung on us when we checked in was inexcusable when paying $600/night. That fee was never listed in the booking description. Our three night stay was almost $1800. which is crazy since there is no complimentary anything such as breakfast or a pool/health facility just a sugar cookie in the afternoon. We had to stay there due to other family members in town for a grandchild’s graduation. I would never stay there again due to the expense.

🇧🇪

Elias

9.1

January 2025

Had a great time at the StayPineapple in downtown Chicago. The hotel is perfectly located for some urban exploration of The Loop. Most tourist hotspots were within walking distance, and the subway (just a 2-minute walk away from the hotel) made it easy enough to visit the attractions further out. During our 4-night stay we had no complaints about the room either. While the bed was not oversized, it was comfortable, and the air conditioning was efficient in cooling down or warming up the room. The building shows its age, especially in the bathroom facilities, but – at least for us – that only adds to the charm and character of this hotel. We did not try the breakfast or the restaurant, so no comment there. Overall we had a 5-star experience and the hotel lived up perfectly to our expectations. We wouldn’t hesitate to book again.

🇺🇸

Keith

9.1

January 2025

I love the location of the hotel. You really feel in the thick of things. Since it was the holidays, the decorations were really fun. I appreciate the little touches like cookies in the afternoon. The public area is comfortable and was very cozy despite the cold weather. I love the whole vibe of the hotel. Best hotel beds I've ever slept in! Also, I had a great view of the NYE fireworks from my window!

The room was a little dark. It could benefit from another lamp or two. The surrounding area is pretty noisy with street musicians etc. (although that is part of the excitement of being in a big city).

🇺🇸

Tommi

10

May 2025

I did not have high expectations, mostly due to rhe name. The name sounded really odd and gave a weird, budget hotel vibe. But I will definitely stay here again. The staff of the restaurant and reception were friendly. The room had high ceilings and spectacular views. The desk was for once by the window and not against the wall. Breakfast is great. And the renovation of the building has been done with great taste.

It’s a small thing but the coffee at breakfast was cold to lukewarm. Small thing and could have said something about it.

🇺🇸

Tanada

10

August 2024

We booked a red eye flight and got to the hotel before check in and their staff was able to get us a room much earlier. Darnell is amazing staff, very friendly, and gave us we needed for our stay. Also we had a great view from our room which overlooked the chicago theater sign. Thank you very much

The water in the bathroom/shower kind of felt unhealthy. I think it could be from the old pipes in the building that the water tasted like rust or iron substance. I hope they can check these pipes out or even the shower lines.

🇧🇷

Thiago

8.2

January 2024

The hotel is extremely well located. Close to Chicago's main tourist attractions. It is located on a street with several shopping options and in front of a shopping center that gives access to Pedway (very important during the harsh winter period). The hotel is also next to the metro station. The hotel restaurant is very good and cozy.

The room is small and the double bed is not comfortable and too small for a couple. Despite being a room with two (small) double beds, it can accommodate only two people reasonably comfortably.

🇮🇳

Mahua

9.1

November 2024

The Vibrant Location. All major shopping store nearby. Millennium Park and River Walkway is at walking distance including the Broadway Theatres like Chicago etc!

No help to get you in the hotel when you arrive with luggages. You are dropped at the road with heavy suitcases and then you have to mange them while opening two heavy doors. Hospitality and warmth to welcome is missing! They don’t even offer to take your luggages upstairs. Very basic hospitality is missing compared to the price you are paying.

🇮🇪

Agnieszka

8.2

December 2023

Location is a big plus, convieniently accesible by blue train coming form the O'hare airport. Everything is nearby, millenium park, shopping and bus stops are around to easy access Navy Pier and 360 Chicago also walking distance to Wilis Tower for skydeck experience. Bed was suuuper comfy!!!

A good bit of noise coming form the L train line which is very is very close but this is not hotel fault. Heating vent directly over the bed was uncomfortable to sleep with hot air and room was too cold when the heat was off. No kettle in the room.

🇺🇸

Timothy

8.2

September 2024

We've stayed here several times. The location is terrific and we love the building. The rooms are quite comfortable and the views of the city are great.

The hotel seems to be struggling a bit. The restaurant was largely empty, even during a holiday weekend. The room was only cleaned once in four nights and the towels were never replaced. The "resort fee" include unlimited (!) water and coffee. Yet we had to ask at the front desk for coffee pods - twice. Please stock your rooms adequately.

Points of Interest Around Staypineapple, An Iconic Hotel, The Loop

Attractions

Marquette Building

0.2mi

Chicago Board of Trade Building

0.4mi

Harold Washington Library Center (Chicago Public Library)

0.5mi

Chicago River

0.5mi

Chicago Pedway

0.7mi

Shedd Aquarium

1.3mi

Chicago Chinatown

2.1mi

Prairie Avenue Historic District

2.1mi

United Center

2.4mi

Chicago Loop

3mi

Trickery

4.4mi

Wrigley Field

4.7mi

Wrigleyville

4.8mi

University of Chicago

6.6mi

Jackson Park

7.1mi

Restaurants

Atwood

Cuisines

  • American

Ambiances

  • Modern

Amenities of Staypineapple, An Iconic Hotel, The Loop

Restaurant

Free wifi

Fitness center

Streaming service (like Netflix)

Air conditioning

Bar

24-hour front desk

Non-smoking rooms

Wheelchair accessible

Elevator

Stay rules - Staypineapple, An Iconic Hotel, The Loop

  • Check-in / Check-out

  • Pets

  • Internet

  • Age restrictions

  • Curfew

  • Parking

  • Reservations

  • Children and beds

  • Cards accepted at this property

Frequently Asked Questions - Staypineapple, An Iconic Hotel, The Loop

Does Staypineapple, An Iconic Hotel, The Loop have accommodations for guests with pets?

Yes, you can stay with your pet at Staypineapple, An Iconic Hotel, The Loop. However, please note that charges may apply for bringing your pet.

When are the check-in and check-out times for Staypineapple, An Iconic Hotel, The Loop?

Staypineapple, An Iconic Hotel, The Loop welcomes guests for check-in at 04:00 PM and the departure or check-out time is set at 12:00 PM.

Is there parking available at Staypineapple, An Iconic Hotel, The Loop?

Yes, there is parking available at Staypineapple, An Iconic Hotel, The Loop. The parking is private and located near the hotel. It costs $75 per day and no reservation is required.

What's the nightly rate at Staypineapple, An Iconic Hotel, The Loop?

Room rates at Staypineapple, An Iconic Hotel, The Loop initiate from $106. Yet, variations occur based on your room and date preferences. For exact rates, please insert your travel dates.

What are the room types available at Staypineapple, An Iconic Hotel, The Loop?

The hotel offers a variety of room types including Double, Suite, and Quadruple rooms. Occupancy ranges from 2 adults and 1 child to 4 adults and 3 children. Smoking is not allowed in any of the rooms. Bed sizes include Double, Queen, and King. Room sizes range from 172 sqft to 398 sqft.

What is there to do in Staypineapple, An Iconic Hotel, The Loop?

Guests at Staypineapple, An Iconic Hotel, The Loop can spend their time enjoying the leisure amenities the hotel has to offer. They can start their day at the fitness center, which is available for their use. For guests who prefer outdoor activities, the hotel offers bicycle rental, allowing them to explore the surrounding area at their own pace.

When it comes to dining, guests don't have to venture far, as the hotel boasts an on-site restaurant called Atwood. With its modern ambiance and American cuisine, guests can indulge in flavorful dishes without having to leave the comfort of the hotel.

Overall, guests have the opportunity to stay active and enjoy delicious meals, providing them with a well-rounded experience during their stay at the hotel.

Does Staypineapple, An Iconic Hotel, The Loop feature its own restaurants?

Yes, the hotel has a restaurant on-site named Atwood. Atwood offers a modern ambiance and serves American cuisine.

Does Staypineapple, An Iconic Hotel, The Loop accept credit cards?

Staypineapple, An Iconic Hotel, The Loop does not accept cash as a payment method. However, they do accept credit cards such as Discover, Mastercard, Diners Club, Visa, American Express, and UnionPay.

From

$106

Call for great rates

+1 (888) 385-6828