Is parking available at the hotel?

Valet parking is available at the property for a fee of USD 75 per night. No reservation is required for parking.

Does the hotel allow pets?

Pets are allowed at the property with a fee of USD 29.95 per accommodation, per night. Service animals are exempt from fees.

What are the check-in and check-out times?

Check-in is at 16:00 and check-out is at 12:00. Early or late check-in/check-out may be available upon request, but additional charges may apply.

What accessibility features does the hotel offer?

The property has limited wheelchair accessibility, including features like step-free entrances and accessible public areas. However, specific details about room accessibility are not provided.

Where is the hotel located in relation to key landmarks?

The hotel is centrally located in Chicago, just a 5-minute walk from the Chicago Cultural Center and City Hall. It is 0.4 miles from the Chicago Riverwalk and 0.5 miles from the Art Institute of Chicago.

What are the hotel's policies for guests staying with children?

Children are allowed at the property, and there is no specified minimum age for kids to stay for free.

Staypineapple Hotel in Chicago

Average nightly price at Staypineapple, An Iconic Hotel, The Loop by month, last 12 months (USD)
Month	Average price
January	US$105
February	US$116
March	US$133
April	US$172
May	US$277
June	US$317
July	US$282
August	US$225
September	US$258
October	US$250
November	US$158
December	US$130

What guests think

At Staypineapple, An Iconic Hotel, The Loop, guests repeatedly highlight the central Loop location, friendly staff, historic charm, and exceptionally comfortable beds, with many also noting clean rooms, nice city views, and convenient touches like refillable water bottles.

Some drawbacks recur: small rooms and older, tight bathrooms, amenity or “resort” fees and billing confusion, pricey valet parking, and occasional issues with streaming or Wi‑Fi. A few guests mentioned housekeeping not daily and intermittent noise from elevators or the street. Overall, expect a charming, centrally located boutique stay with welcoming service and great sleep quality.

Facilities

Cleanliness

Rooms

Service

Location

Dining

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AI-generated summary based on recent guest reviews

Facilities

On-site restaurant and bar are convenient and generally appreciated, though breakfast service can be slow. Valet parking is expensive, and a few guests reported delays or confusing processes.

Related guest reviews

10

JODIE

22 Apr 2025

·

Stayed 1 night

Fantastic location, great price. Needs better parking.

8

Jean

10 Nov 2025

·

Stayed 2 nights

Awesome location! Great bar and food! Best value in this area for sure!

10

Eric

14 Oct 2025

·

Stayed 1 night

Clean room, restaurant food was good, staff polite. Appreciated the historical feel and visually appealing interior of the hotel.

10

James

28 May 2025

·

Stayed 2 nights

Very nice hotel with nice staff and a comfortable bed. Just be prepared to pay for parking !

10

Pamela

31 Dec 2024

·

Stayed 1 night

The Atwood restaurant has great food, very helpful and pleasant staff but thay need more servers.

10

Kelly

3 Nov 2025

·

Stayed 1 night

Incredibly friendly front desk staff! Hotel was very clean and comfortable. Wish the bar was open later on a Saturday night

8

DeVonna

8 Dec 2024

·

Stayed 3 nights

Everything was good up until when I checked out and the valet took an hour to bring my car.

8

Lauren

4 Oct 2025

·

Stayed 3 nights

Great location and staff. Terrible parking options.

10

Daniel

16 Jul 2025

·

Stayed 2 nights

Loved the small details like getting a pineapple reusable waterbottle and free pineapple cookies. Great that they have free bikes for the guests to use. Great rooms and good restaurant.

8

Eileen

15 Jun 2025

·

Stayed 4 nights

The hotel property is a little tired but that's part of its "iconic" charm. Food in the restaurant was good but the service was spotty, at least at breakfast (ate there three mornings in a row). I had to ask twice to get things I ordered and it was hard to get my server's attention when it was time to pay.

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AI-generated summary based on recent guest reviews

Cleanliness

Rooms and public spaces are frequently described as very clean. A handful of reviews note worn or stained bathroom grout/fixtures and occasional paint or tub issues, and housekeeping is not provided daily.

Related guest reviews

10

David

1 Nov 2025

·

Stayed 1 night

The room was pleasant, though there was a stain in the bath tub. The bed was very comfortable and I slept like a stone. However I had some difficulty using ithe TV remote control, the battery may need to be replaced. The staff is wonderful. Sashon at the front desk was very helpful in resolving a transportation problem. Altogether a very pleasant stay.

10

John Perry

12 Aug 2025

·

Stayed 3 nights

Almost everything was perfect about the property and our stay - and we are planning to return. Our ONLY criticism is that the bathroom (#805) needed some "deep cleaning": The seal/grout around the tub was mold-stained, and the floor tile grout was in dire need of a good deep cleaning. But for that, everything was pretty much perfect. We love the building, the location, and the view down State Street. The bedding was luxurious, though in the warm weather we wish there was a "lighter" option than the wonderful "coverlet" provided.

6

Valerie

21 Feb 2024

·

Stayed 4 nights

Beautiful historic building, comfortable bed. Room wasn’t cleaned in the 4 days we stayed. Parking is 75$ per day if you use their valet- use Spot Hero!! Extra cost for basic amenities.

10

Kelly

3 Nov 2025

·

Stayed 1 night

Incredibly friendly front desk staff! Hotel was very clean and comfortable. Wish the bar was open later on a Saturday night

10

Joseph

7 Oct 2025

·

Stayed 2 nights

Very clean and fun.

4

Duane

26 Nov 2024

·

Stayed 1 night

The new paint in rooms were very strong and can’t sleep. They put me in another room and still smell of paint but not strong but a little dirty

10

Faith

17 Nov 2025

·

Stayed 2 nights

Room was very clean, staff courteous! I love the place!

10

Alison

10 Apr 2025

·

Stayed 1 night

Great hotel. First time stay for me, and I will definitely be back. I travel for work, and the location was convenient, rooms were clean and comfortable, amenities were outstanding, and staff were super friendly.

10

Kylie

28 May 2025

·

Stayed 3 nights

Beautiful and clean hotel with super comfortable beds!

6

Thomas

26 Jun 2025

·

Stayed 2 nights

Thumbs down on policy of not cleaning rooms every night

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AI-generated summary based on recent guest reviews

Rooms

Rooms feel comfortable with very plush beds and good city views. Many are small, and some guests experienced dated or compact bathrooms, occasional elevator or street noise, and inconsistent TV streaming or Wi‑Fi.

Related guest reviews

6

Constance

28 Dec 2024

·

Stayed 4 nights

The room was very small and close to the elevators, one of which was very noisy and clunked against something every time it moved. So loud, it shook the room! We’ve stayed here many times, but this was by far the worst room. The front desk staff when we arrived was busy chatting with her boyfriend, and was fairly abrupt with us. Otherwise, the staff was terrific, as we’ve come to expect. Gracious and helpful.

10

Rebecca

13 Oct 2025

·

Stayed 2 nights

The room was small, but comfortable. The bathroom was a slightly odd logout because the door opened in right in front of the vanity so it was impossible to have the door open and stand in front of the vanity at the same time.

8

Wendy

20 Oct 2024

·

Stayed 1 night

Beautiful view, nice room we are locals and we just wanted a relaxing night in the downtown area, how ever when we came back to the hotel the WiFi wasn’t set up for us Tv wasn’t able to stream so we were stuck with local tv and only a couple channels. Because of the location we might comeback but nothing out of standard stay

10

David

7 Sept 2025

·

Stayed 2 nights

Lovely staff, nice spacious room and super comfortable bed. What’s not to like Well, one thing: the shower head was terrible. Not in keeping with the rest of the experience.

8

Darla

18 Aug 2025

·

Stayed 2 nights

Streaming service didn’t work on our tv.

10

Tim

20 Apr 2025

·

Stayed 3 nights

Fantastic views of downtown, from full glass windows.

10

Nick

7 Apr 2025

·

Stayed 4 nights

This is a great hotel to enjoy a lot of what Chicago has to offer. It's location lets you use fantastic public transportation options and puts you right in the middle of most of the sites a tourist in Chicago would want to see. The staff was always courteous and helpful. We had to get their help to receive some extra bedding and get some other questions answered throughout our stay and they were always courteous and answered quickly. We were unable to get either streaming device in the bedroom or the main room to work throughout our stay and, our internet connection reset several times forcing us to call down to the front desk and have them reset it. But, these are small concerns when weighed against the entire stay.

8

Katrina

29 Aug 2025

·

Stayed 2 nights

This hotel had a terrific location within walking distance of many Loop attractions. Staff was friendly in the rooms were smallish but clean. I didn't find this hotel to be exceptional apart from the beautiful elevator area. I would recommend that future visitors who are driving park in the Grant Park North garage. Very convenient!

10

Machaelie

29 Aug 2025

·

Stayed 3 nights

Location was outstanding. Atmosphere is great. Most comfortable hotel bed I think I’ve ever slept on. The restaurant is very nice. Staff were so kind and helpful. Will absolutely book again next time we visit Chicago.

10

Gil

9 Nov 2025

·

Stayed 1 night

Great views, quiet

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AI-generated summary based on recent guest reviews

Service

Service is widely praised as friendly, welcoming, and helpful across the hotel. There are occasional complaints about billing or amenity‑fee communication, slow restaurant service, or valet issues.

Related guest reviews

10

Noel

7 Sept 2025

·

Stayed 1 night

Great hotel. Front desk was very outgoing and personable. Convenient location...close to everything.

2

Rachel

2 Feb 2024

·

Stayed 2 nights

My car was vandalized while in the care of the valet at StayPineapple. The valet said nothing, I noticed the damage immediately and went back to discuss it with the front desk. They said I'd have to take it up with the valet company - I had to prod them to get the name and contact information of the company. The man running the valet disappeared as soon as he handed me the keys and we were not able to talk to him, despite trying to contact someone in the valet office while on site. Otherwise, the hotel was quite lovely.

10

Linda

28 Nov 2025

·

Stayed 1 night

We first walked in and got greeted immediately. The gentleman at the desk was very friendly and attentive, joking with my kids and making them laugh. He explained everything about the room and the hotel. Made us feel like we were at home. Thanks for such great hospitality!

10

Shannon

28 Jul 2025

·

Stayed 1 night

Love staying at this hotel due to stellar location, service, and cleanliness! I am a repeat customer and will be back again soon.

8

DeVonna

8 Dec 2024

·

Stayed 3 nights

Everything was good up until when I checked out and the valet took an hour to bring my car.

10

Kathyrn

5 Jun 2025

·

Stayed 1 night

Having stayed at all of the Staypineapple hotels in WA and OR, my daughter and I have set out to stay at all of the Staypineapple properties. This one was no exception, to the exceptional service we have been accustomed to receiving. Luxurious suite. Our Everything person even brought a microwave to our room when we requested to heat up the most amazing Italian meal we'd ever had at nearby Quartino's.

10

Kendra

23 Aug 2024

·

Stayed 3 nights

Fantastic location right in the heart of the Loop. The staff was all super friendly and helpful and the rooms were immaculate.

10

Jon

16 Oct 2023

·

Stayed 3 nights

Best staff we've experienced in any city at any hotel. Every single staff member was excellent, friendly and went above and beyond our expectation.

6

Nicholas

4 Dec 2024

·

Stayed 1 night

Booked a short trip to do some holiday things in Chicago. Great location downtown near where I wanted to go. Room was small but nice. Old building but nicely renovated. Valet parking for an extra fee. The stay was fine but make sure to have extra money on hand for all of the fees. I was charged the price of the room and a $50 incidentals fee upon checkin. Pretty standard. Then after checkout I was charged again an even larger amount, and sent an email only with the total. I had to call and speak to 3 people to get an itemized receipt sent to me where I discovered they charged me twice for early checkin and all the taxes that go along with that and charged for the entire stay a second time. I had to work my way up to get to speak to a manager about the double charges and she said they always charge the full amount of the stay plus $50 as an incidental, and that I would receive the funds back as well as a refund for the double charges for early checkin. The only concession I received for their mistake was a refund of their $30 amenities fee, which there were virtually none of anyway. A nice hotel and nice staff but this situation put a bad taste in my mouth. It probably happens often and they get away with it because guests don’t check into it. Luckily I had the funds for the extra and double charges.

8

Eileen

15 Jun 2025

·

Stayed 4 nights

The hotel property is a little tired but that's part of its "iconic" charm. Food in the restaurant was good but the service was spotty, at least at breakfast (ate there three mornings in a row). I had to ask twice to get things I ordered and it was hard to get my server's attention when it was time to pay.

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AI-generated summary based on recent guest reviews

Location

Excellent central Loop location within easy walking distance of Millennium Park, theaters, shopping, and CTA trains. Ideal for exploring downtown.

Related guest reviews

10

Brayan

28 Jul 2025

·

Stayed 3 nights

Great property for experiencing Chicago. All of the L stations are just a few blocks away, giving access to anywhere you could want to go. One block down from Michigan Ave and Millennium Park. Beautiful city views, nothing beats the Chicago Skyline

10

Timothy

18 Jul 2025

·

Stayed 1 night

Perfect location to launch from to see the city.

10

Melanie

9 May 2024

·

Stayed 5 nights

Great hotel in a great location! Very friendly, clean, fun, with a fun restaurant in the hotel.

10

IFAN

10 Oct 2023

·

Stayed 4 nights

Great location, service and the food was top notch

10

Scott

18 Dec 2023

·

Stayed 1 night

Great location - service was good, room was clean. Building looks amazing and valet was not an issue. You can see the history in the building in a good way. KrisKringle Market and Theater district is a block away, see photos.

10

Eric

15 Mar 2024

·

Stayed 1 night

Amazingly comfortable, easy access to the red/blue line, and the most friendly staff!

8

Katrina

29 Aug 2025

·

Stayed 2 nights

This hotel had a terrific location within walking distance of many Loop attractions. Staff was friendly in the rooms were smallish but clean. I didn't find this hotel to be exceptional apart from the beautiful elevator area. I would recommend that future visitors who are driving park in the Grant Park North garage. Very convenient!

10

Machaelie

29 Aug 2025

·

Stayed 3 nights

Location was outstanding. Atmosphere is great. Most comfortable hotel bed I think I’ve ever slept on. The restaurant is very nice. Staff were so kind and helpful. Will absolutely book again next time we visit Chicago.

10

john

2 Jul 2025

·

Stayed 3 nights

Great location and central to everything you could possibly want to walk to in Chicago. Staff were so friendly and helpful. Taxis that were needed when it was not a walkable destination were cheap and easy to access. As was Uber. Highly recommend

10

Kyra

13 Jun 2025

·

Stayed 3 nights

Beautiful hotel in a great location.

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AI-generated summary based on recent guest reviews

Dining

Most guests enjoyed the on‑site restaurant and bar and appreciated the welcome drink. Multiple reviews mention slow or spotty breakfast service, limited menu at times, and so‑so coffee or beer selection.

Related guest reviews

10

robert

26 May 2025

·

Stayed 2 nights

Great location....good food.. .below average coffee

8

Mary

22 Feb 2025

·

Stayed 2 nights

The staff were polite, the room was comfortable and the bedding was very nice , The food from the Atwood restaurant was great value for money and delicious

10

Eric

14 Oct 2025

·

Stayed 1 night

Clean room, restaurant food was good, staff polite. Appreciated the historical feel and visually appealing interior of the hotel.

10

NANCY W

10 Oct 2024

·

Stayed 1 night

Pineapple is within walking distance of Goodman Theatre and we are patrons. We stay at Pineapple each night we attend a play rather than take a late train 1 1/2 hours home. We especially like the bedding and the restaurant serves a nice breakfast. We have tried supper there, but the breakfast is the best.

10

Pamela

31 Dec 2024

·

Stayed 1 night

The Atwood restaurant has great food, very helpful and pleasant staff but thay need more servers.

10

Vanessa Marie

15 Mar 2025

·

Stayed 4 nights

Amazing and friendly staff, the attached restaurant is also yummy and has great options.

10

Deanna

24 Mar 2025

·

Stayed 2 nights

Great place to stay with outstanding restaurant and great service. Comfy beds.

10

Laura

12 Nov 2025

·

Stayed 2 nights

The staff was great. The hotel was really cool. It preserved the historical aspects of the building and udated where it needed to. The restaurant was great and the server was super nice. I also loved the refillable water bottle and sparkling water!

8

Eileen

15 Jun 2025

·

Stayed 4 nights

The hotel property is a little tired but that's part of its "iconic" charm. Food in the restaurant was good but the service was spotty, at least at breakfast (ate there three mornings in a row). I had to ask twice to get things I ordered and it was hard to get my server's attention when it was time to pay.

8

Paula J

20 Apr 2025

·

Stayed 4 nights

Lovely hotel, very comfortable beds, quiet, good location. Offered a complimentary beer/wine but the bar was out of beers on tap and had only High Life and Heineken the four days we were there.

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AI-generated summary based on recent guest reviews

Su	Mo	Tu	We	Th	Fr	Sa
				1 $326	2 $419	3 $377
4 $416	5 $634	6 $779	7 $500	8 $495	9 $942	10
11 $1,103	12 $402	13 $481	14 $426	15 $502	16 $222	17 $683
18 $573	19 $1,043	20 $920	21 $523	22 $374	23 $343	24 $323
25 $245	26 $296	27 $316	28 $366	29 $260	30 $212	31 $238

Staypineapple, An Iconic Hotel, The Loop

Prices for Staypineapple, An Iconic Hotel, The Loop

Monthly average prices

About this property

Location

Room options

Atwithood Queen Mobility Accessible with Roll-In Showither

Reliance King Suite Mobility Accessible with Tub

Reliance King Suite

Burnham Twitho Double Mobility Accessible with Roll-In Showither

Millennium Park View King Suite

Burnham 2 Two Queen

Burnham King

Atwithood Queen Mobility Accessible with Tub

Burnham Twitho Double Mobility Accessible with Tub

Atwood Queen

Guest reviews of Staypineapple, An Iconic Hotel, The Loop

Who stays here?

What guests think

Property policies

Check-in instructions

Good to know

Optional extras

FAQs about Staypineapple, An Iconic Hotel, The Loop

Prices for upcoming dates

Su	Mo	Tu	We	Th	Fr	Sa
		1	2	3	4	5
6	7	8	9	10	11	12
13	14	15	16	17	18	19
20	21	22 $769	23 $754	24 $288	25 $314	26 $334
27 $224	28 $596	29 $567	30 $529