Name: Staypineapple An Iconic Hotel The Loop Chicago
Address: 1 W Washington Street, Chicago, 60602, US

8/10

Excellent

22 Jul 2026

Susan

Nice room with a view of the Chicago theater & Macy's in the old Marshall Field building. Super convenient to take buses or El trains. We were happy that we came from O'Hare and were able to take 1 train and be within a block of the hotel. When we checked in, we were supposed to get a \"Welcome drink\", but they told us they were out of them. Huh? The hotel bar was 20 ft. away. They offered us one for the next night, which was nice. I got a beer that the hotel bar offers. They had 2 bottles of wine at the reception desk that I guess the bar doesn't sell. It was all kind of silly. Pineapple theme is a gimmick but it's cute I guess. Great historic building with beautiful architectural details - that I really liked. BEST, fluffiest towels ever! Also, we had drinks at the bar that first night & loved our bartender, Gabe. He made some amazing espresso martinis that had some ancho chili oil in them! Gave a subtle heat - really interesting & delicious. Overall it was a nice stay & great location!

10/10

Exceptional

20 Jul 2026

Kevin

We loved our stay at StayPineapple. The name is strange but the hotel is awesome. Very historic but still very clean and updated rooms. In the heart of Chicago we will definitely stay here again for sure.

10/10

Exceptional

19 Jul 2026

Muhammad

Great historic building expertly converted to an iconic hotel. As an architect I was thrilled to stay in the historic Reliance building.

Self

10/10

Exceptional

19 Jul 2026

David

Great location with easy access to everything. Spacious rooms and a great staff. Rates were very good.

Self

8/10

Excellent

19 Jul 2026

Teresa

It was nice and in the perfect location.

Friends

10/10

Exceptional

18 Jul 2026

Bronya

We had a wonderful stay at Staypineapple Chicago! The entire hotel was incredibly clean and well-maintained from the lobby to the room. The amenities are fantastic—we loved the quirky touches, the incredibly comfortable beds, and the fun afternoon treats. A huge thank you to the staff, who were consistently helpful, welcoming, and quick to assist with anything we needed. One big tip for future travelers: The hotel charges $75 for valet parking. My recommendation to everyone is to download the ParkWhiz app and check for parking nearby ahead of time instead. You will save a ton of money!

Friends_and_family Family

10/10

Exceptional

17 Jul 2026

Philip

Great room, lovely environment. Close to all forms of transportation. We used the L train, and bus and foot to get around. Free sparkling water refills kept us hydrated.

Partner

10/10

Exceptional

17 Jul 2026

Jared

This is our third stay at this property. The location cannot be beat!!! Central to everything including the red line if you plan to use the train. Make sure you get your Welcome drink, pineapple sugar cookies, and reusable water bottle from the room. The staff is always wonderful. The iconic Macy’s is across the street and you are steps from Goddess and the Baker…yum.

Family

10/10

Exceptional

16 Jul 2026

Joseph

Location. Close to everything.

Partner

10/10

Exceptional

15 Jul 2026

lornise

Great stay great location great staff.

8/10

Excellent

15 Jul 2026

Jeffrey

The property itself was amazing. Definitely a different style of place to stay. It had an old, but well maintained feel to it. The room was clean, the vallet made things super easy, plenty to do and eat within walking distance, and the restaurant in the lobby was spectacular. I had two complaints about our stay: 1.) Included as an amenity was the ability to screen share to the TVs in the rooms. We were not able to use that amenity. Some of the rooms had issues and we were told I.T. was back logged and couldnt fix it. 2.) We specifically got a room, with a separate bedroom behind closed doors, for privacy from our children. There was nothing private about the two thin glass doors and see-through shades over the glass. We had to put a sheet over the window just to change clothes, so our kids didn't see us. Also, the king bed came with two thick nice twin sized covers. We asked for a king sized blanket and they brought us a cheap blanket that had their logo on it. We weren't in the room that much, so the blankets were the most bothersome issue. We do enjoy watching a show before bed though, it would have been nice to watch one on the TV.

Friends_and_family Family

10/10

Exceptional

14 Jul 2026

Vera

Location was great, but has street noise at night

Family_with_children

10/10

Exceptional

12 Jul 2026

Gail

Was happy to return for another stay. As always, was cozy, comfortable, and quiet.

Friends_and_family Friends

10/10

Exceptional

11 Jul 2026

Nicholas

I liked the attention to us. Offering water bottles, wine, and snacks. I appreciate the staff holding onto our luggage while we waited to be checked in. This made it possible to enjoy the city longer. My only suggestion would be to walk guests over to the bar/restaurant area and introduce them to the staff.

Partner

10/10

Exceptional

11 Jul 2026

Christine

Great location, rustic but feeling super clean, comfortable bed, great city view, walking distance to the millennium park and pretty much everywhere. Helpful and friendly staffs. Definitely will come back!

Business

10/10

Exceptional

11 Jul 2026

Amy

The staff was very helpful with wayfinding and suggestions for activities

Friends

10/10

Exceptional

09 Jul 2026

Alexa

Absolutely spectacular hotel- loved the real key locks, soap dispensers instead of wasted plastic, and water fillers. Incredible views from the room too!

Friends_and_family Friends

6/10

Pleasant

08 Jul 2026

arlene

Conveniently located but a bit drab

Partner

10/10

Exceptional

08 Jul 2026

Kirsten

The room was spacious for Chicago & the bed was very comfortable. The staff was very friendly and accommodating. I would definitely stay here again.

Friends_and_family Friends

10/10

Exceptional

08 Jul 2026

Andrew

The location was perfect - staff was friendly and helpful! We will definitely come back.

Family

8/10

Excellent

07 Jul 2026

Zoe

Beautiful historic building; dog friendly!

Partner

8/10

Excellent

06 Jul 2026

Ryan

Small room. Not very clean, but the building is really old so, whatever. Valet is $75 plus tip. They charge you $50 for “incidentals” and another $30 for room perks or something. So be prepared to pay a lot more money after your room rate. Great view and the bartender in the lobby was wonderful. Everything else about this place was meh.

Partner

10/10

Exceptional

05 Jul 2026

Victor

Great hotel right in the heart of downtown Chicago! Very clean rooms with a light hearted theme. Free glasses of wine when checking in. Free water refills as needed! Bed was amazing!!!

Partner

10/10

Exceptional

05 Jul 2026

Jing

good

Partner

10/10

Exceptional

04 Jul 2026

Joshua

Right next to The Loop and Millennium Park; great location.

Self

8/10

Excellent

04 Jul 2026

Leslie

Nice hotel, fun, great location! I do wish there were places to refill your water bottles on each floor, but I love that hotels are starting to do this.

Partner

10/10

Exceptional

02 Jul 2026

Liza

La atención hacia mi mascota y detalles en el cuarto fue increíble, Lo único que en recepción deberían de tener a alguien que hable inglés y español, Para poder hacer preguntas y dudas que uno pueda tener ,Por lo demás el señor del vallet parking fue muy amable y hablaba español nos aclaro bastantes dudas ,En general si me volvería a ospedar sin duda alguna .

Pet

10/10

Exceptional

01 Jul 2026

Crissa-Jean

.

10/10

Exceptional

01 Jul 2026

Julie

The room was spacious with a very comfortable bed.

Self

10/10

Exceptional

29 Jun 2026

Janet

Upon arrival, we were offered complimentary cookies and coffee, two free drink coasters, and in our room was a PineappleStay water bottle! The staff are great. The entire hotel is immaculate. The location is perfect. We absolutely enjoyed our stay here!

Partner

10/10

Exceptional

29 Jun 2026

Kayla

We really appreciated the baby-friendly amenities, well lit room, and comfortable bed. We will definitely stay again.

Friends_and_family Family

10/10

Exceptional

28 Jun 2026

Dianne

All the staff was very helpful and polite

Partner

10/10

Exceptional

27 Jun 2026

Emilee

Staff was very nice!

Partner

10/10

Exceptional

25 Jun 2026

Tammy

We had an issue upon arrival when we discovered that the room reserved for us was a queen room instead of the king room we had specifically booked. Fortunately, DeJuan immediately stepped in to help and made what could have been a frustrating situation much easier to navigate.

DeJuan was professional, patient, and genuinely kind throughout the entire process. He took the time to address our concerns, worked to find a solution, and made us feel valued as guests. His positive attitude and willingness to help stood out and turned our experience around.

Beyond resolving our room issue, DeJuan also went above and beyond by recommending a great local place to eat. His friendliness and knowledge of the area made us feel welcome and well taken care of.

Excellent customer service can make all the difference, and DeJuan is a perfect example of that. We truly appreciate his help and hope he receives the recognition he deserves.

Partner

10/10

Exceptional

24 Jun 2026

Gail

Beautiful historic building, with nice updates. Wasn't sure about the duvets (2 on the bed so one for each of us) but they worked! Stay with the Pineapple.

Partner

10/10

Exceptional

24 Jun 2026

Derek

Great location and friendly/helpful staff.

Self

10/10

Exceptional

23 Jun 2026

Bryce

A fantastic boutique hotel. Rooms were great, views were amazing and in the heart of it all. Highly recommended.

Friends

8/10

Excellent

22 Jun 2026

Laura

The hotel itself was amazing. Very clean and well taken care of. The staff was fine, not bad, not good. My complaint is regarding the valet service. We had to wait a long time for the valet to take our car when we arrived and it was 20-25 minutes to get it for us when it was time to leave. That is frustrating.

Friends_and_family Family

2/10

Poor

21 Jun 2026

Tonia

VERY small and old rooms. Towels smelled awful. Dingy carpets. Zero functioning amenities. Staff was very unhelpful. Called the front desk at 11 pm to ask for help with the streaming service and was told, \"It's late. Call back in the morning.\" The only redeeming quality was the location. I wouldn't have such a negative impression of the hotel if it was rated two stars but it was rated as \"exceptional\" and that is 100% inaccurate. Holiday Inn Express vibes at best.

Partner

10/10

Exceptional

21 Jun 2026

Hancy

Some of the doors didn’t close all the way, like the bathroom door, which may have been due to seasonal expansion from winter to summer.

That said, the staff was wonderful. We were getting ready to go out Saturday night for dinner and drinks when the dress I planned to wear suddenly had a tear. Thankfully, housekeeping was cleaning the room next to us, so I stepped out and asked if they happened to have a sewing kit. She immediately called a colleague, and within less than 10 minutes, I had one in my hands — truly my saving grace!

The staff was very sweet, and they do a great job keeping the place clean and tidy. I also appreciated how conscientious they were about water bottle preservation, and the water filling station was actually really nice, with options for different water temperatures, sparkling, or still.

Overall, we had a great time. Thank you — we will definitely be back!

Partner

10/10

Exceptional

21 Jun 2026

Liz

Beautiful historic hotel building, lovely room and amenities in room. Bar and restaurant were awesome, great food, drinks and vibe. Will stay here again!

Family

10/10

Exceptional

20 Jun 2026

Carrie

Location is perfect!!! Directly adjacent to bus and train. Held our bags both before check in and after checkout. The hotel and rooms are quirky and fun, everything was very comfortable and we enjoyed it. The breakfast restaurant (not included) was spectacular!!!

Family_with_children

10/10

Exceptional

20 Jun 2026

Barbara

Be aware that to park with them it costs $75 per day for valet parking only. There is no parking garage available. When I read that valet parking was \"offered\" and I didn't see the cost, I thought I'd just self-park in their garage. But that is not an option. When we arrived there was only one valet and it took quite awhile (15-20 minutes) to hand over my keys. Retrieving my car was quick, but it was not a busy time.
The hotel is lovely and our room was clean and comfortable. It's within easy walking distance to the Chicago Theater which is why I chose it.
Ate breakfast at the small but sunny restaurant and it was reasonable and very tasty.
I recommend this place for a cozy downtown stay.

Friends_and_family Family

10/10

Exceptional

20 Jun 2026

LEWIS

Very clean and very helpful staff-resturant was wonderful. Coffee maker and bed shams???

Friends_and_family Friends

10/10

Exceptional

18 Jun 2026

MARY E

Always very nice, great location and building

10/10

Exceptional

17 Jun 2026

Michael

Great staff! Hosted at restaurants was excellent ‘!

Family_with_children

10/10

Exceptional

16 Jun 2026

Michelle

Fantastic place to stay, especially if you are looking to walk around the city. Super convenient location and amazing accommodations. The staff were super helpful and valet parking made getting in and out super easy.

Partner

8/10

Excellent

15 Jun 2026

Sharon

We loved character of the building and the proximity to downtown. However the hotel was not as secure as others. Anyone from the public could access elevators. Also a $25 amenities fee was attached for cookies, water, and bikes. We did not need or use any of these.

Family

10/10

Exceptional

14 Jun 2026

Steven

I'm officially a Staypineapple fan! Great branding. Attentive, capable staff, cool vibe. Awesome location.

Partner

6/10

Pleasant

13 Jun 2026

John

Room was clean, and comfortable although quite small. Valet parking was terrible despite being costly, the “free” amenities have a value of perhaps 5 dollars but the “amenity” fee is $25.00. Taxes, non-optional fees, parking costs, etc can easily make the final costs more than 150 per cent of the advertised price for a night’s stay, and lack of a doorman, any bellmen, at most two front desk people, and one valet make this a hotel that has nice rooms and no service and much personal inconvenience. Being hip and cute is not good enough.

Partner

10/10

Exceptional

13 Jun 2026

Dorothy

Like the green policy and the ecopour coffee without dirty filter cups and plastic containers for coffee.
Stylish architecture and details of historic building.
Convenient to subway stations.

Self

10/10

Exceptional

13 Jun 2026

Jessica

Darnell at the front desk was so warm and helpful. Our room was as pretty and cozy as it gets, the view to die for. The restaurant downstairs has the best French toast on earth. For reals!

Friends

8/10

Excellent

13 Jun 2026

Wren

Greta location, beautiful building and rooms (high ceilings, huge windows), and a great restaurant downstairs (under different ownership). We stayed here last two years ago and it feels not as well managed as it was then. In room furniture/sofa was very stained, curtain was hanging off the hooks, lots of paint dents, staff less engaged etc. I wish they were doing a better job of maintaining this beautiful property. We may be back due to the strong points, but I will search other options as well in future.

10/10

Exceptional

13 Jun 2026

Marlena

Great spot in the city with convenient valet parking. Big, clean rooms with tall ceilings. Comfy beds and great water pressure. Would definitely stay again. Dog and baby friendly

Family_with_children

8/10

Excellent

13 Jun 2026

Philip

Good location, friendly staff

Self

10/10

Exceptional

11 Jun 2026

Diana

Such a fun hotel! Great location, classy interior, and eco-friendly water. This would also be the best choice if you’re traveling with a dog.

Partner

6/10

Pleasant

08 Jun 2026

Melanie

Mixed stay with lacking housekeeping but decent room. Resort fee is ludicrous for what you get.

Self

6/10

Pleasant

07 Jun 2026

Lynn

We stayed 4 nights in 2 rooms (a couple and a solo traveler) and while the location is the hotel's strongest point. It is a historic building in the Loop, walkable to Millennium Park and easy transit access.
A few things could be improved. Our check-in experience was a bit awkward as the host assigned the smallest room to the couple rather than the solo traveler, which felt like an oversight. The lobby seating is showing wear, and the in-room bedding instructions were more confusing than they needed to be.
At $500+ per night, we expected more. Housekeeping is every other day, which felt inadequate at this price. The mandatory amenity fee is also frustrating, not because it's unexpected, but because it's hard to justify keeping it separate from the room rate.

Family

10/10

Exceptional

07 Jun 2026

Myung Joon

All aspects have met to my satisfaction, I would definitely come back when I go to Chicago. Thank you.

Partner

10/10

Exceptional

31 May 2026

Kerry

It was great

Family_with_children

10/10

Exceptional

30 May 2026

Brian

Best hotel in Chicago!

10/10

Exceptional

27 May 2026

Debby

Such a lovely hotel with a beautiful, excellent staff, and lots of character!

Partner

8/10

Excellent

26 May 2026

kelly

The property has a lot of character and it is centrally located. We really enjoyed being able just to walk outside of our door and have access to so many great things in downtown Chicago. The room was very small and the bedding was extremely comfortable. One thing to note, after paying the premium price some of the amenities included water bottles in our room and coffee and Wi-Fi. But upon checking out, it was actually $25 per day to have one water bottle and coffee in our room. It’s not really an amenity if you pay for it. Just wish that was upfront instead of an added cost of $50 to our weekend you don’t have an option for those amenities, but they should be already included in the price. The restaurant that just opened was not great as well. I don’t think it is affiliated with a hotel but it’s in the lobby of the hotel and we had breakfast and it was about a five out of 10. The staff were incredibly helpful and welcoming.

Family

10/10

Exceptional

26 May 2026

yijing

Good

10/10

Exceptional

25 May 2026

Jeremy

The staff is super friendly and easy to talk to so you don’t have to worry about much! The location is amazing if you wanna explore downtown Chicago!

Friends

10/10

Exceptional

25 May 2026

Yolanda

It was a great stay. Staff were helpful. Wish the restaurant was open during our stay.

Self

10/10

Exceptional

24 May 2026

Elaine

Lovely view from the room. Very Chicago

Family

10/10

Exceptional

23 May 2026

Teah

Great experience! The pineapple shortbread cookies sealed the deal for me!

Partner

10/10

Exceptional

18 May 2026

cary

a great stay in the loop, a convenient location to all the sights and sounds of Chicago

Partner

8/10

Excellent

17 May 2026

Sharon

Enjoyably quirky hotel--pineapple theme, free water (still, sparkling, or hot) in the lobby, European-style comforter, actual keys (not a key card), one-of-a-kind in-room coffee maker. Good location for bargain shopping (Nordstrom Rack, Uniqlo, Primark); easy walk to Art Institute. The newly-opened restaurant in the lobby has a menu that strains the conception of fusion past its breaking point and the service is a work-in-progress. Not too many other food options in the immediate area.

Self

10/10

Exceptional

17 May 2026

Brenda

Clean rooms, comfy bed.

Partner

10/10

Exceptional

17 May 2026

Cynthia

The staff was beyond amazing! They were cheerful and incredibly helpful. They were patient with questions and requests and truly seemed to enjoy their jobs! The room had so much charm and very helpful amenities (robes, iron, extra blankets, a free water bottle, free coffee, fridge, blow dryer, etc.). I don’t believe all the rooms have a great view but ours had a fantastic view of N. State St., with a perfect view of the Chicago Theatre, and a great view down Washington Street right to Lake Michigan!! It was so nice to be able to sit with a coffee in the morning, enjoying the beautiful views! I highly recommend this fantastic hotel and will definitely be going back!

Friends_and_family Family

10/10

Exceptional

17 May 2026

Kari

Our room was spotless, staff was helpful, and our bed was so comfortable.

Friends_and_family Family

10/10

Exceptional

15 May 2026

Beth

Easy access to many points of interests and shopping

Self

10/10

Exceptional

14 May 2026

Spencer

Traveled with my wife, used the bikes to cruise along the water. Great time!

Partner

10/10

Exceptional

12 May 2026

Susanne

I love this neighborhood , great for shopping and walking.
The hotel was super cool with original architecture.

Family

10/10

Exceptional

11 May 2026

Deborah

Funky hotel. Great location. Good vibe.

Partner

10/10

Exceptional

09 May 2026

Jacqueline

This is my favorite hotel ever! I love that the integrity of Daniel Burnham's elements hae not been tampered with, which adds to the overall charm of the place. The staff--particularly Sashon(?) were extremely helpful in helping me get transport to Navy Pier. I love the new restaurant, where I had breakfast-perhaps the best toast ever! The entire staff is welcoming, helpful, and convey a high degree of hospitality. It is located close to the CTA--a big plus when coming from O'Hare. I frequently travel alone, so the high degree of safety at this hotel is always a comfort.

Self

10/10

Exceptional

07 May 2026

Scott

Great location in the heart of the loop. Super friendly and attentive staff. An older building, but clean and well-maintained. Would definitely stay here again.

Partner

10/10

Exceptional

05 May 2026

Carol

yes.

4/10

Poor

01 May 2026

Devon

Good location but terrible experience. There was one staff member who was kind and helpful when we checked out but the other two I encountered were really unpleasant. I usually don’t have a car in cities but I needed one this trip due to my work conference being outside the city with no easy transportation to and from. The valet situation was a nightmare! One of the morning I called for my car and no one answered. I walked down to the front desk and the gentleman actually rolled his eyes and huffed at me after I asked for my car to be retrieved. It took 20 minutes and I was late for my conference. The next day I woke up extra early and called a half an hour early to accommodate for the time it takes to get the car and it ended up taking 35 minutes. I was in tears and again late for my conference. Overall not a good experience and would not recommend. The place is outdated and the pillows are not comfortable.

Partner

10/10

Exceptional

01 May 2026

Eva

The staff were fantastic, and the beds were insanely comfortable/blankets were soft and plush. The location is advantageous- lots of shopping, food, and things to do nearby. Getting an Uber from this location was a breeze and took less than five minutes. The Valet service for Staypineapple was also good. Would definitely recommend!

Family

10/10

Exceptional

30 Apr 2026

Jessica

Clean, friendly and perfectly located.

Friends_and_family Family

8/10

Excellent

28 Apr 2026

Amy

This is a well-located hotel with an unbeatable front desk staff. We were warned that the room would be cleaned only every other day of our 4 night stay; however, it was never cleaned or straightened up. The room also needs more light. A standing lamp behind the chair would have helped immensely. That said, when I complained about the cleaning, the absolutely wonderful front desk staff immediately both apologized and adjusted our bill. I would stay there again but...

Friends_and_family Friends

10/10

Exceptional

27 Apr 2026

Bradley Joseph

Amazing spot, centrally located, great views

Partner

8/10

Excellent

27 Apr 2026

Justin

Nice building, perfect location

Self

8/10

Excellent

26 Apr 2026

Lucy

Well located for transport links.
Comfortable bed with everything you need.
Rooms are well soundproofed. The building has nice original features.

Partner

8/10

Excellent

24 Apr 2026

Daniel

Very Pleased

Partner

10/10

Exceptional

24 Apr 2026

Anne

I don't usually write reviews-but this hotel is a little gem. Lots of unique touches that make it stand out: amazing bedding, attention to detail with towels & robes, dog friendly, with an option to buy a stuffy for pet rescues, nice staff & a cool aluminum water bottle souvenveir.

Self

8/10

Excellent

23 Apr 2026

Michael

Overall felt it was very average and a lot of form over function. The gym is small and could have been cleaner. I laid on the floor for abs and my shirt was filthy. Rooms seem older with some Pinneapple themed updates. Chromecast did not work. Shower made a loud banging noise and did not get as hot as it should have been. It is nice they give you a drink upon entry. They also charge a $30 amenity fee at checkout.

8/10

Excellent

21 Apr 2026

Sarah

This property is in a great location. The staff were friendly and the room was clean. The room we were in was very small and used. The building is really cool but we were super disappointed with it being under construction with no place to hang out and have a drink. We weren’t notified of the construction until right before our stay. We would have chosen somewhere else because of this.

10/10

Exceptional

18 Apr 2026

Robert

Wonderful restaurant, amazing food.

Family_with_children

10/10

Exceptional

17 Apr 2026

Phil

Comfortable and a really great team working therr

8/10

Excellent

16 Apr 2026

Zachary

Lobby was under construction which wasn’t attractive but also not disruptive. Hotel was fine but not glamorous. Room was small.

Self

10/10

Exceptional

15 Apr 2026

Diane

Convenient location, walked everywhere. Great staff, so helpful amd accommodating.

Business

10/10

Exceptional

14 Apr 2026

Jason

Nice hotel, close to a lot of things

10/10

Exceptional

12 Apr 2026

Paula

Great location in downtown Chicago near good restaurants, performing arts venues, the lake, etc. Friendly and helpful staff. Cosy and comfortable rooms. Quiet at night so great for sleeping.

Partner

10/10

Exceptional

11 Apr 2026

Cristina

Darnell was the absolute BEST!!

Family_with_children

10/10

Exceptional

08 Apr 2026

Silvana

Yes good