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    Staypineapple, An Iconic Hotel, The Loop

    4.3 (300 reviews)
    Open Open 24 hours

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    View from our room
    Nick M.

    Great experience here. Recently in town for a wedding. Staff was very friendly and let us check in early. Room was clean and spacious. The metal water bottle in the room was a nice touch. The view from this building was amazing (see pic). Very conveniently located by several cta stops too. Only complaint was that they do every other day cleaning unless you ask, but they did not clean our room even after asking. That being said, would happily come back here.

    Bed
    Seanniece B.

    Ok, this review is going to be very balanced. Booking - the booking process was seamless. Very straightforward. When I arrived, I was in their system with a reservation. No problems there. Check in - check in was very simple. The awesome Darnell gave me the rules, checked me in and told me to hold on tight to my keys they have regular keys, not FOB keys. The building - the lobby is very posh, up dated. Very well polished. You come in and see the hotel restaurant which is very modern and stylish. The walls were some sort of polished stone. Overall, the hotel looked like it was an old bank or old hotel but modern. So truly iconic in that way. Hotel room - okay, so, the wow factor of the lobby, hotel, and hotel room hallways didn't necessarily translate into the hotel room itself. The hotel room needed some attention to detail and upgrading. For instance, the bathroom needed to be recaulked and glazed. Also, the sheets had makeup on them. Unfortunately, the blankets smelled unwashed. Staff - which brings me to the staff. The young lady (light skinned black woman) addressed my sheet issue and answered my questions about wifi. She was really sweet. Darnell was also amazing. He pulled out all the stops for me. There were some staff who weren't very pleasant and that's not ok. Amenities - they have some good amenities like you can borrow bicycles and umbrellas, free cookies and coffee in the lobby, free wifi, and a complimentary drink on arrival. However, there was no microwave. I've been to boutique hotels and there's usually at least a central microwave so that was odd. There's also no washer/dryer on site. That's not as startling. I don't think I've encountered one at a boutique hotel before. The good parts were good. The view -- stunning. It was a cool, trendy spot but the hotel rooms need some TLC.

    My partner accidentally left her wallet at ORD and the front desk staff was there when we realized it-- this was in the room when we got in!
    Stephanie G.

    Stayed here for one night on my birthday to attend a show. This is my go-to hotel for any Chicago stay. Love the discount for repeat customers. It's a charming hotel in a great location and they took extra good care of us this time.

    Shower
    em o.

    The good: if you Iike blankets, you get two. This means you don't have to share if you're sharing a bed. However, there is no top sheet. There is a mini-fridge, and the extra toilet paper roll decorated like a pineapple is cute. The bad: The shower in our room is a drain in the bathroom floor. For the amount of money that you pay to stay here, you'd hope to get a bathroom experience that's a tad bit better than the bathroom at home (an actual tub or a shower ledge). Get ready for water to travel around the shower curtain, and to soak the bath mat, which is really just a glorified hand towel. If you enjoy camping and roughing it in the woods, you'll enjoy this shower experience. If not, well, I guess that I'm just thankful I had a place to shower after a hot day roaming around the city and riding on public transit. (I'm not sure if this is standard for all rooms, so I suppose that it may be wise to ask.) The worst: Do not make your reservation through a third-party site. Otherwise, you may find that Staypineapple will not honor the price that you originally paid, and will reduce the room stay to only one night. Had Staypineapple tried to work with us, I think we would have had a better experience here, in spite of the "shower." The pineapple aesthetic is cute, but when it's coupled with an unexpectedly modified reservation and an underwhelming shower, it doesn't do much. All in all, if you're going to stay in the loop, go for a hotel that offers an actual shower.

    Evening view at nighttime such a dream
    Diana G.

    I stayed almost two full months here and honestly I would have loved to stay much much longer; however the rates soared during St. Patrick's celebrations and I had to check out. I have extremely fond memories of this property when it was called the Burnham hotel owner by Kimpton boutique properties. The one thing I love the most about this hotel is how much the staff treats you like family instead of a client and the layout of the hotel rooms feel like apartments instead of a hotel space. Each room has extremely high ceilings making the room feel extremely spacious and upon check in they gave me an extremely beautiful room with a view of state street and the old Marshall fields building. I felt like royalty and so did my dog Mr. Troika. Cassandra who is a supervisor at the front desk is incredibly warm, welcoming and very passionate about making the guests here feel special. I chatted with her the first evening and told her about me experiences at the Burnham and mentioned how the VIP members would receive a welcome gift of your favorite snacks and goodies. She decided to surprise me and had someone bring me up a plate of fruit, nuts and beautiful macarons all different pastel colors and soda pop. I was overwhelmed with how kind Cassandra truly is and she always gave my dog as many pup cups filled with whip cream as he could possibly handle. What really melted my heart is the fact that many of the original housekeeping staff remembered me from my previous visits to the Burnham too! They also go out of their way to provide excellent service constantly checking up on me and asking if I needed service or extra towels or clean glasses. The Staypineapple truly is an example of everything a hotel truly should be. Another thing I loved was having a room key This hotel is a historical landmark building and each room comes with its own solid brass ornate key with a pineapple logo on each key. I much prefer this feature to a keyword. The manager of the kitchen even went out of his way to talk to me and we had wonderful conversations and his staff even treated me to a completely complementary salad when the salad place next door was closed too early. The kitchen has a happy hour too where you can get a delicious burger and beer or pop for only $10 which is a super value too. Each afternoon there is a cookie hour and every day you receive drinking cards so you can choose any beverage you want from beer, wine, a soda pop, a hot chocolate, coffee or an iced latte drink. May I also add my pup Mr. Troika Celebrated his 3rd birthday here and Cassandra surprised him by presenting him with a huge dish of vanilla ice cream and caramel topping. He was overjoyed and I wish to thank all the staff here for being so kind to him till he eventually broke free of his shyness. If you have pets there are pet amenities here! They provide doggie beds, cute doggie treats, doggie poop bags and dishes for your pet if you need them. I wish to also add that you will receive your own water bottle to keep which you can refill daily with fresh sparkling or still water that is provided in the downstairs lobby. Beth Anne and Cassandra did their best to work within my budget and waived certain fees so I could stay longer here. The only sad part of this visit was the day of departure. If I were a millionaire I'd buy a room here permanently just for myself to enjoy the vibes are that Good! A huge thank you to everyone that made me feel so special.

    Derrik B.

    We found StayPineapple for under $100 per night and they also have buy two get one free when booked 21 days in advance. Located just west of the bean, the hotel offers a historic feel with metal old school keys and lovely dark wood and white tile throughout. The bed offers TWO comforters which was a welcome site, and boy were the cozy beds! This place is the most pet friendly hotel of 2024, and we have not had a better experience in a hotel while staying with our dogs. The staff made it so welcoming and easy to check in, and we enjoyed a quiet part of the hotel with our three dogs. The bar and restaurant were excellent and offered a nice beer and spirit list. The staff here is what set this hotel apart for us, and we look forward to visiting again soon.

    Sunil R.

    This hotel is a classic. It took me a while to think through if I found it too kitschy or if I liked it and landed on the latter. There are pineapples everywhere!! They give out actual keys to the rooms as opposed to the cards. Everything feels classic including the facade, the lobby, and the elevators. Very cool. The rooms are nice and comfy. Fantastic prime location. The staff seems a little on the curt side but that's ok.

    Coffee station
    Alesia S.

    I had never heard of this hotel brand until I had to book a room for a work trip. The staff was extremely welcoming and explained the details of the location thoroughly. They also provided great, local recommendations for bars and restaurants in the area. Michelle and Cassie were extremely hospitable. The room was cute and I love the features like the sustainable water bottle and the afternoon snack time.

    Ryan C.

    I was glad that I was able to to book this hotel for the first two nights of our trip since we missed out on it our last trip. We're familiar with the chain and just love all their hotels so we had some high expectations. We had a late flight so we didn't get to the hotel until close to 1 AM. The lobby was pretty empty but huge since the restaurant/bar is right next to the check in desk. The guy who helped us check in was nice but seemed exhausted but made things go quickly. Very cool part is that you get an actual key to open your door instead of a key card. The hotel is on the older side and you can kind of see that in the room but it was still nice looking and pretty clean except some parts of the bathtub. The room wasn't too big but it was good enough for the two of us. The bed was stiff for us but it was clean. The shower's water pressure was very strong which I thought was great. Only thing we were really missing here was the slippers that StayPineapple hotels have. We did love the view of the street we got in our room. It was a short stay but overall it was a solid, well priced, and clean hotel in a great location and I would definitely come back next time we go to Chicago.

    Hotel coupon provided for a latte
    Jennifer Z.

    Fun & friendly! Not luxury, but great location especially for the parade and welcoming. We played "Uno" in the lobby with the kids, and the kids also enjoyed the pineapple cookies.

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    Ask the Community - Staypineapple, An Iconic Hotel, The Loop

    Can they hold luggage if your flight is hours after checkout?

    yes, they can - just ask the desk!

    Is this hotel geared toward swingers?

    I didn't see anything while staying there that would make me think that and I've stayed in two separate occasions.

    View All 3 Questions

    Review Highlights - Staypineapple, An Iconic Hotel, The Loop

    Was in the city just to hang out and meet up with old friends and decided to stay at Staypineapple in the Loop.

    Mentioned in 32 reviews

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    Staypineapple, An Iconic Hotel, The Loop - hotels - Updated June 2026

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