I stayed at this historic hotel a number of times in the past when it was the Hotel Burnham, a Kimpton hotel. It then apparently became Hotel Alise before becoming part of the Staypineapple Group. This was my first stay at a Staypineapple property; I must say their vibe is charming with a good dose of humour. The hotel building itself has a significant history. Originally designed by the famed architecture firm Burnham and Root as well as by Charles Atwood in the late 1800's as an office building, it was one of the first to feature the large bay-like "Chicago window". Its transformation into a hotel has thankfully retained much of the original features and fixtures, even the interior windows of individual offices still exist but are opaqued. Room doors still have the "Reliance" name on the lock and also the original mail slot. The first floor still features the front desk and the all-day restaurant Atwood, which I did not try this visit. Staypineapple has added a welcome drink, bikes to borrow, a water bar, afternoon pineapple-shaped cookies and coffee, plus snacks and beverages for purchase. My room was the starter-level Atwood Queen. It was petite but was not lacking in any features. There are pineapple motifs throughout: the free refillable water bottle, mugs, pillow, extra toilet paper, robes, outlet/USB port dock, Do Not Disturb sign, stuffed dog (you can buy). There are 2 covered quilts that also serve as topsheets. The window was enormous, even though not a Chicago one. I was on the top floor and had a tiny glimpse of the river, along with the L, the Chicago Theatre and the historic Marshall Fields building (now Macy's). I appreciated the empty mini-fridge. Being in the downtown loop, many sites and restaurants are easily within walking distance, as well as CTA stops. I personally went to Millennium Park, the Chicago Architecture Center, and Wildberry, the very popular breakfast/lunch spot. Staypineapple has added some fun to this iconic hotel, which will remain my first choice for lodging in the Loop. read more

See all

I became a fan of Staypineapple when I first stayed at a location in Seattle. So now if I'm traveling, I see if there is one in the city where I'm going. Chicago's location is in the Loop, a nice central location. Unlike the prior hotels, this hotel is in a historic building, so instead of card keys, you have old fashioned keys for your room, and the bathroom fixtures are also old fashioned, as are the walls in the elevator lobby. Everything else, though, is quite modern. I truly appreciate that the bedside table had easily accessible sockets to plug in my electronics. I love that our room has two luggage racks. Staypineapple also provides two duvets per bed (which I understand is European style) so you can't gripe about your partner stealing the covers. And of course, you get a free metal water bottle that you can fill with water in the lobby, plus coasters to get two free drinks. We didn't spend much time in our room--when we travel, we want to see the city--but the time we did spend was very cozy. Check in and check out were quick and efficient. (Pre-checking in online helps.) If I'm ever back in Chicago, I'll stay here again. read more

Stayed with a group at the Stay Pineapple hotel, otherwise the name may have put me off... Situated in the Chicago loop across from Macy's (former Marshal Fields flagship store). Walking distance to many restaurants and the river, Nordstrom Rack is even located in the same block. You will find this place convenient. The hotel is historic and comes with the beautiful architecture and quirks an older hotel will have. Very clean, wonderful beds and linens. The hotel restaurant has a simple but tasty menu. All in all, a great stay and I would recommend you give it a try. I'll be back. read more

See all

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. read more

See all

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. read more

See all

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. read more

Staypineapple, An Iconic Hotel, The Loop - 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! - Hotels Near Me - Chicago, Illinois

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. read more

Staypineapple, An Iconic Hotel, The Loop - Shower - Hotels Near Me - Chicago, Illinois

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. read more

See all

Such a cute hotel with the pineapple theme! It was clean, the staff are friendly, and the beds are comfortable. It's also in a great location. read more

We stayed on Sat March 14th. Centrally located within the theater district. We also saw the river being dyed for St. Patrick's Day and did the architectural boat tour. Everything was within easy walking distance. We received excellent service from Sashon & DJ who were very friendly and went above and beyond to make us feel welcome. They were very accommodating not only to us, but as I was waiting in line, I witnessed them helping other customers with directions and suggestions to local attractions. This is the 2nd time we have stayed when seeing a show, and this is our go to when staying in the theater district. Rooms are very clean, with great views of the city. Beds are very comfortable. Will definitely stay again. read more

Staypineapple is the hotel my Fiancè booked for my birthday trip to his hometown and I have nothing but positive things to say! Darnell at the front desk was super kind and hospitable, always friendly and welcoming every encounter we had with him! Thank you, Darnell! The rooms are spacious and the beds are so comfortable that it was hard to get out of bed each morning! There's a restaurant located in the lobby and although we did not eat there, we did sit at the bar for drinks and the manager helped us out one morning by assisting with a favor and we very much appreciated it! You are provided two complimentary drink coupons when you arrive to the hotel and they also have bikes for your use, which we did not get to use on this trip but appreciate the option! There's also a water station for the refillable bottle provided in your room. I highly recommend the hotel as it is centrally located to many things and not a far walk at all for us to the many things I wanted to do. We will definitely stay here again in the future. read more

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. read more

See all

We loved our stay here! Staff was very friendly and helpful, our room was always very clean, and the hotel gave all of us (three guests) free drink coupons every night. The restaurant was to die for, we went to breakfast there twice! It was close to all of our activities which was very convenient. I'm taking off one star only for the fact that the bar ran out of vodka for two nights while we were there! I guess if you're getting free drinks out of the deal you shouldn't expect too much but we were a little shocked :) read more

i really liked staypineapple in Chicago and am glad i booked it. main pros-- -- gorgeous building inside and out. they've renovated the old building while maintaining it's character very well -- very central -- friendly accomodating staff, in a way that felt very comfortable and enjoyable to come in and out of the hotel -- nice room and views from the room -- loved the bedding and sheets, they claim is higher quality and I'd have to agree -- amenities like the water bottle, bikes, etc are all good main cons -- -- it's probably unavoidable but the street noise is a little annoying due to Chicago drivers love for honking -- the room gets warm and the ac doesn't do an amazing job rotating the air out -- the bathroom is a bit cramped. they did what they could with the size but yeah -- the restaurant downstairs isn't the most convenient. i didn't get breakfast there because they told me they take 20-30 minutes to prepare any food. but at night they have last call kind of early as well overall really enjoyed my time there and would stay again read more

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. read more

See all

Overall, a solid experience. The bed, as advertised, was extremely comfortable and definitely the highlight of the stay. We LOVED the double duvets. For as central as the location was, it was actually pretty quiet on our floor, so we both slept well. You get welcome drink coupons upon check-in, which we used for coffee and juice on our way out. We were staying here during our cross-country move from MA to WA, so our car was pretty packed with stuff. Luckily, they had hotel carts we could use. It's in a pretty busy area of Chicago so we didn't want to leave anything in our car at night. Valet drives your car to a lot about 4 blocks away; they don't have their own garage or anything. Definitely do the parking package for a discount. It is a dog-friendly hotel, however, it's VERY important to note that there are not any grassy areas nearby (not even trees or tanbark patches). I was expecting a dog-friendly hotel would at least have a little turf patch somewhere for dogs to go potty. The parks nearby do not allow dogs either, and security kicked us out. I did think it was a little pricey, but on the other hand, you're paying for the location. It's walkable to Cloud Gate, and we recommend Wildberry Pancakes for breakfast. read more

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. read more

See all

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. read more

Staypineapple, An Iconic Hotel, The Loop - Hotels Near Me - Chicago, Illinois

See all

This is NOT the Atwood I remember. From start to finish with this place it was a disaster. I ordered multiple snack packs before arriving and didn't get a bunch of the items I paid for. The room was filthy - hair tumbleweeds on the floor, wrappers around the living area. Things were also broken - a pipe in the bathroom under the sink leaked and we stuck the garbage pail under it because it was bad and this was at bedtime so we weren't about to either call and have to change rooms or have a repairman in here. Blinds were Broken, chips on wooden furniture. The room, even though an executive King, was tiny. They'd be better off with pocket doors because you can't fit more than one person in the bathroom without hitting something and if traveling with kids, it is horrible to try to accomplish baths. Same with the bedroom French doors - unnecessary and a huge space sucker. Better insulation for windows is needed as well with the constant ambulance and police sirens at night. And, the Wi-Fi was awful. The instructions to be able to stream Netflix or other apps to the televisions never worked either, so forget movie night because they have no premium channels on the tv. And one last comment - if you advertise on your in-room tv that there will be eggs hidden in the lobby (presumably for children to find) perhaps think about what this looks like in practice. read more

See all

Stayed here for 3 nights and it was awesome! Great hotel, super comfy rooms, delightful staff, amazing location. Would definitely stay again! read more

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. read more

See all

This was one of the coolest hotels I've stayed in. Fun fact this was one of the only buildings that survived the Chicago Fire so I felt pretty secure in staying on a high floor. There's a eatery when you first walk in to your left, though we didn't indulge in any items from here. The decor was so cool and pineapples are everywhere, even pineapple cookies that were delicious. I kept expecting to see SpongeBob and Patrick in Bikini Bottom, lol. We stayed in a suite and enjoyed the beautiful views from our room. The room was cozy and plenty of space for 2 people. We had robes which were very comfy to lounge in. The bed was spectacular and so comfy. We really enjoyed our stay and would return. It's in a great location and the charm is on 1000. All staff were friendly and hospitable. read more

See all

I stayed here for a night during my stay in Chicago. I wanted a hotel close to Millennium Park, with quick access to restaurants, shops, and bars, and this hotel was one of them! The hotel is on a busy street, close to the shops and the park. I did valet parking since I wanted to avoid the hassle of finding street parking during that busy afternoon when I arrived in Chicago. The hotel is decorated nicely with holiday decorations. When I arrived at the hotel, it was extra busy with people trying to check in, and the crowd was rushed. I checked in, and this hotel is super-friendly to your pets with a pet fee. You can get bowls for your dog at the front desk, and when you get to your hotel room, they have this husky stuffed toy you can purchase, and half the proceeds go to an animal shelter. To enter the hotel room, you get your turn-in key like back in the day. The front door reminds me of the front door, where you have a slot where an old letter carrier would slip in your letters to your room; it was a nice touch when the owners of the hotel remodeled the whole hotel completely but left old details such as that to make it a unique lodging that separates it from other hotels around the area. Once you get situated, after you unpack all your stuff, you can enjoy a great meal and drinks from the restaurant and bar in the hotel's lobby. The food was delicious when I stopped by here for dinner and drinks. I enjoyed my stay at this hotel. I highly recommend this place to those traveling to Chicago who want a pet-friendly hotel in the middle of the shopping district and within walking distance of many things and Millennium Park. read more

Staypineapple, An Iconic Hotel, The Loop - Hotels Near Me - Chicago, Illinois

See all

Great place to stay. Needed to be in Chicago for six days for business. Picked the staypineapple for my stay. What stood out for me the most was the staff, very friendly and helpful people. They came across as sincere and very friendly people, loved it. Location is perfect. If you're into shopping you're in the close proximity of more than enough and close to the magnificent mile, but the field Museum is also closer than when I was staying in River North. Close to subway/metro stations, right across the corner. And a ten minute walk to Union/Oglivie if you need to go to the suburbs (Some sweet villages there). Building and room itself; spacious enough room, great bed. The building has got character in a good way, because it's kind of classy. read more

Very iconic hotel. Great staff, bedding, and the Atwood restaurant. HOWEVER, no security and there SHOULD BE! Random homeless people allowed to come in the lobby by the bar/restaurant and "wash themselves " at the water fountain provided for guests to fill their "iconic pineapple water bottles". I watched him for 5-10 minutes before anyone said anything to him, until he walked out on his own. This should be addressed, the need for door security. read more

Stayed here for 3 nights over the weekend while visiting Chicago. You can not get more central than this! It's on a corner smack middle of downtown, down the block from the famous Chicago theatre, a few blocks from the Cultural museum and Millennium Park. Eateries, walgreens, Garrett's popcorn just all outside no more than a block. I thoroughly enjoyed my stay here with a few hiccups here and there. First off, The "Naked Experience" was amazing! The most comfortable bed, sheet, pillow and personal duvet was heavenly! I had the best sleep. So much that I just went on their website and purchased the bedsheet and some pillow cases for my own bed! I just wish they sold a large king size duvet because I would purchase it immediately! Although the Queen size room was small it was perfect for 2 people. Views of downtown. I would say that on the website when I booked this room, it states that it comes with both a bathtub and shower combo and it was just a bathtub. I would have the listing updated because it's misleading! What else did I enjoy? Free coffee, free waters, 2 free welcome drinks downstairs. When it downpoured on our last day, we had a free umbrella we borrowed for the day. The robes were comfy. I even enjoyed having an actual set of key versus key card. The building is old and vintage and with a set of keys, it felt more like entering an apartment vs a hotel room. We stayed for 3 nights and it aint cheap but we only got room service for 1 day. Not sure why we were skipped a day??!?! Overall, good stay and I would stay here again. Just minor fixes here and there. The "pineapple" theme is cute. Though, not sure if there's any connection to "swingers" although pineapple is is also a symbol of hospitality. read more

See all

Cassandra!! And Sashon!! And Maya!! The hotel was charming and comfortable. Our suite was perfect. The real jewels were the staff! All three went the extra mile to make our trip happy and memorable!! read more

First time staying at this hotel. So impressed. Loved the charm, the outstanding "down to earth" kindness and customer service from the entire team and amenities. At first I was taken aback when handed physical room keys (versus key cards), but it absolutely matches the hotel's essence. The beds and down comforters were the best. My favorite part of this trip was meeting Cassandra at the front desk! SHE IS AMAZING! Her warmth, positive attitude and professionalism was so refreshing. She assisted me with finding neat dining spots to eat, listened so well and was just so engaging. She is an incredible representation for this boutique hotel and will be the reason I come back! Loved how the hotel stayed on brand with the pineapple theme everywhere, super cute. Will absolutely stay here again. read more

See all

The gentleman working at the front desk named Darnell was absolutely amazing. From the moment we checked in he was awesome and then upon checking out I wasn't feeling well and he kept checking on me to make sure I was feeling better. Aside from the rooms being perfect for a two person stay the customer service was above and beyond my expectations. Will definitely be staying here again and recommending it to my family and friends! P.S. give Darnell a raise!!! read more

Staypineapple, An Iconic Hotel, The Loop - Queen bed in our room for two guests - Hotels Near Me - Chicago, Illinois

When the hotel for the conference I was attending was totally booked, I started looking around for someplace nearby for accommodations and hit on StayPineapple, the quirkiness of which appealed to me (and the fact that they are pet friendly. I wasn't traveling with my dogs, but never turn down an opportunity to pet one!). This was a good choice. I arrived early in the midst of a downpour and came in looking, no doubt, like a drowned duck. Despite it being early, they found a room for me to change and dry off (and even swapped it for another when I asked for something a bit further removed from the elevators). The hotel is quite charming with Art Deco flourishes and cute pineapple- themed touches. My room had lovely view of State street from the 11th floor and was comfortable and clean. The room comes with a reusable aluminum water bottle and has a recycling receptacle as well as trash can. It also comes with a little stuff animal dog that costs $25 if you take it, but then they donate the proceeds to animal rescue organizations. The beds and duvets are very comfortable. The room also comes with very soft robes, although I didn't try out this feature. There is a restaurant on the ground floor--Atwood--with a nice bar. After I arrived I had lunch there and enjoyed it (Korean BBQ chicken sandwich, with very good fries). Prices are certainly metro Detroit prices, but on par with other restaurants in the area. The staff were all very friendly. Overall, I really enjoyed my stay and would certainly stay at StayPineapple again on a future trip. read more

Take this review with a grain of salt. Stay Pineapple, An Iconic Hotel, was a bit of a letdown for me, mostly thanks to one particular employee, a half clean room, and the pandemic. Check-in was after 4PM on 4/3/2021. Check-out was by 12:00 p.m. on 4/6/2021. We were allowed to leave our car at the curb out front while getting our hard copy keys and bringing our luggage up to our room. The room was admittedly smaller than I anticipated even though I read the reviews and can tell by the pictures this would be so. In our room, the smoke alarm was half hanging off of the wall. The bathroom was marginally clean. Quite a bit of long hair everywhere that wasn't mine. I paid for two nights and got a third free for a deluxe room with two queen beds and private bath. The rate on 4/3/2021 was $149.00 and on 4/4/2021 was $169.00. There was also a nightly amenity fee of $15 (multiply that times 3 even as the third night was free... fees still apply!). Altogether with the city, county and state lodging fees, my bill came out to $426.20. My brother asked the front desk person in-person to have a new towel sent up. After waiting nearly 12 hours, it never happened. I'm guessing that because he forgot to wear his mask back down the elevator that the female night employee sloughed his request off. Ultimately the point of the matter is she said she would have it sent up and didn't follow through. This was just one of a few unfortunate interactions with her. There were no cute little pineapple cookies like they kept advertising. The same front desk person rambled on about how they are shipped in from Seattle now and all of the local bakeries weren't good enough for the sweet tooth aficionados, meanwhile talking smack about the higher ups that made these decisions. She was a real Debbie downer. I love the details inside and on the building itself. I even like the fact that they still use real keys. It's within walking proximity to an array of places in Downtown Chicago. A short drive to others. However, parking is not included in your Staypineapple bill. And they recommended the mediocre parking garage at Wabash and Rudolph. Their website mentions another one, but in person they mentioned this one. If you use this garage, I recommend the mobile app "SpotHero" to save a little on money. TIPS + dog-friendly hotel + beach cruisers are available for checking out the local sights OVERALL It was a good experience overall, however, a moderately clean room and that one employee with whom my brother and I interacted on several occassions made only half efforts to ensure a marginal sense of hospitality. read more

See all

Chose this hotel as its central to all the sights my mini-me and I were going to explore while in Chicago. When looking at hotels, I really loved the decor and history of the build. Fun fact: It was the first Chicago building that had large full glass window panes, which was a big deal as windows were typically smaller. Our checkin was great, got a room early which is always appreciated and was upgraded to a corner suite. They give you drink cards for a complimentary treat which was appreciated. Great cappuccino in the lobby restaurant. Will definitely stay here again when I'm back in Chicago. read more

See all

Loved the location of this hotel. Central to everything we wanted to see during our 3 day stay. All the major sights were walkable. It's a historical landmark. It used to be Reliance built in the 1890s- a building designed by Burnham (who designed the Chicago World Fair), then the Burnham Hotel, and now Staypineapple. The inside is beautiful, the doors use actual keys instead of key cards. The staff is really friendly, helpful, and welcoming. You get a complimentary drink at check in. The view from our room was great. They're smaller rooms, but that was something we didn't mind considering we spent most of our time sight seeing during the day. read more

Darnell was a great start to our visit. He was friendly and welcoming and took it upon himself to treat us to a cupcake because we were celebrating a birthday. Clean room, quiet hotel, excellent location, near stores, and CTA. Beds were very comfortable and the space was just enough. read more

See all

The first room I got put in had the most gorgeous view! I asked to be put in a room with 2 beds, the first room had a bed and a pullout. They moved me right away, absolutely wonderful service. The beds are crazy comfy BTW, the blankets are the best part. Cool, fluffy, and amazing on bare skin. Sashon made the trip unforgettable, he really takes care of guests and gets to know everyone. read more

No need to consider any where else to stayPineapple in Chicago. This hotel is friggin' AWESOME!!! Old school, they use actual room keys! Cassandra at the front desk was the perfect representation of how you'd want your guests to be greeted. This hotel is one of the few structures that survived the Chicago fire (thank you Cassandra for sharing the history). It feels throwback to a bygone era of speakeasies and Al Capone. I don't know if someone gave Cassandra a script of what to say and how to greet guests, but I think it's actually just her innate ability that made the first impression so impressive. Everything about this hotel is five star....ultra cool and hip. This coming from someone who is about to enter their sixth decade lol read more

See all

Stayed here for work and the pineapple theme is cute. Pineapples everywhere. Check-in was easy. The room was clean. There was a complimentary drink. Overall a great stay and you're around the shopping! Restaurants around there do close early, so make sure to check what's open early on. read more

Staypineapple, An Iconic Hotel, The Loop - Hotels Near Me - Chicago, Illinois

See all

Absolutely love this hotel! So many thoughtful and cute pineapple themed options throughout experience. Even when arrive you receive a delicious pineapple sugar cookie that I loved so much I bragged at check out about it and they gave me another one! Very cool old building with great location. Hard to compare this to any ordinary hotel experience as I loved the theme and thoughtfulness of whole experience. Even had comfy pineapple robe for each guest. Always trying to find reasons to stay here and live locally because it's so fun! read more

See all

This past April, I attended a conference in Chicago. I decided to spend a couple of extra days in the windy city to do some sightseeing. My friend from Chicago recommended a few spots to stay, with the Staypineapple being her favorite. I'm so happy I took her up on her recommendation as this hotel is awesome. And I'm not just saying that because my favorite fruit is pineapple. First off, the hotel is in a great location centrally located just a block or two from Millennium Park and the bean plus many popular attractions, restaurants, and stores. Upon check in, they give you a pineapple cookie which was a nice touch. The hotel is very much pineapple-themed with pineapple-shaped toilet paper, and other pineapple decor. It's funny. They also set up their beds and provide robes to encourage you to sleep naked so hey if that's your thing you're in good shape here. It's a historic hotel so that aspect is nice too. Super clean, super comfortable, you can't really ask for much more. They also have a hotel bar and restaurant. As part of your stay, you get $10/day to spend where you see fit. Food, drinks, or snacks. The drinks are overpriced but it is a hotel bar so it is to be expected. I would gladly return the next time I'm in Chicago. read more

We stayed here in the Fall 2021, Winter 2022, and Spring 2022 so it was like our home away from home and the staff treated us as such. The rooms are smaller but they are well appointed and being in the old Hotel Burnham made it unique and memorable. The location is wonderful and we had the pleasure of spectacular views from each of our rooms. We had rooms ending in 07 and each time we went up floors. We also went to the Atwood for food and drinks a few times and we're well taken care of. read more

See all