Staypineapple, An Iconic Hotel, The Loop

“Amazing experience. Love this place. Just one negative point.”

My stay in june 24 was very pleasant. The hotel is in the heart of the city and has cozy rooms, very stylish and with a very special charm. The bar always has a good atmosphere and is the perfect place to end a long day, whether on business or on vacation. The fact that the hotel has a gym is fun... more

My stay in june 24 was very pleasant. The hotel is in the heart of the city and has cozy rooms, very stylish and with a very special charm. The bar always has a good atmosphere and is the perfect place to end a long day, whether on business or on vacation. The fact that the hotel has a gym is fundamental for me, so I took advantage of it a lot. I would like to highlight the kindness and good disposition of all the hotel staff, their professionalism and good vibes and the desire to always help, especially the reception team. I would especially like to highlight William from the front desk team, who was a great guy, had great details and made the checkout very easy for me, since having such a long trip back home, it is wonderful that someone makes everything easier for you. The only negative point I can point out is that at checkout I was informed that the amenities were not included in the room price, and the charge was more than 70 USD, something that I had not been personally informed of beforehand and that I understood that it was included in the hotel (as in all the hotels I visit for work around the world) when I read that I could drink all the coffee I wanted on a label that you find with this equipment in the room (it was the only thing I consumed in the room). I will definitely stay at this hotel again when I return to the city.

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“Charming, with some quirks (and hidden fees)”

This hotel had a perfect location, great view, friendly staff, and charming art-deco setting, but beware a few quirks. First, the $20 daily amenity fee essentially only covers a metal water bottle, water fountain refills, and occasional sugar cookies (good, but not $20 each good!). We were encour... more

This hotel had a perfect location, great view, friendly staff, and charming art-deco setting, but beware a few quirks. First, the $20 daily amenity fee essentially only covers a metal water bottle, water fountain refills, and occasional sugar cookies (good, but not $20 each good!). We were encouraged to take the water bottle everywhere––it felt like we were paying them to advertise their chain. Secondly, housekeeping visited rarely (once) during a 3 day/3 night stay. We often had to request more essentials: towels, coffee, mugs. Our room was spacious but the bathroom and shower left some to be desired. This hotel is great for a quick mini break to explore a fun and lively area of Chicago, but would likely pass on another stay unless we found a super good deal. (A cheaper in-house restaurant would also help, considering how much we paid for our stay).

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“A great stay in a great city”

We stayed in the Staypineapple Chicago early June 2024 for 4 nights. Initially, we were allocated Room 410, being told that it was a “quiet room” . However, the room looks out to an internal space with an old air con unit and a dusty old broom. Not a great start, however this was remedied by M... more

We stayed in the Staypineapple Chicago early June 2024 for 4 nights. Initially, we were allocated Room 410, being told that it was a “quiet room” . However, the room looks out to an internal space with an old air con unit and a dusty old broom. Not a great start, however this was remedied by Michelle and Darnell the next morning, moving us to a wonderful from with a great street view from the 11th floor . Darnell was also really helpful with local knowledge … what a star!! Thanks Darnell. The beds in both rooms were super comfy and the hotel and rooms were spotlessly clean so we would definitely stay here again, just not in Room 410 lol 🤣. The Hotel is brilliantly located for all metro lines and right in the centre of The Loop, so not far to walk for most sights. We loved Chicago ❤️and its people who couldn’t have been more friendly to us. Can’t wait to come back!!

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“Surprisingly disappointed”

Overpriced and underwhelming. For background, I came to Chicago solo for a special event for 3 nights. I really wanted to stay here bc it looked cute, had excellent reviews, and the stuffed dog (not gonna lie!). I signed up for their program to get a discount but 1 night of my stay was sold ou... more

Overpriced and underwhelming. For background, I came to Chicago solo for a special event for 3 nights. I really wanted to stay here bc it looked cute, had excellent reviews, and the stuffed dog (not gonna lie!). I signed up for their program to get a discount but 1 night of my stay was sold out online. So I waited to see if someone cancelled. I kept checking online and called their main number twice, but they kept saying sold out. But then I found a room in Priceline. Hmmmm.....?!? I ended up spending about $1,600 for 3 nights?!? Ridiculous, and totally my fault...but they charge a huge amenity fee. Pros: -pineapple theme is cute. Cute sugar cookies given out everyday. Cute stuffed dog in your room that you can buy for $25 and an *unknown* amount goes to rescue shelter. -bed was really comfy. I like the double duvet situation. -robes were comfy! -great location; walkable to everything and super close to subway. I took the subway here from the airport and it took about 50 minutes. Cons: -front desk staff are not warm or welcoming (don't know how they got such glowing reviews before?!?). They sit super low down behind front desk so you really only see eyeballs peering at you. They give short answers. I felt like I was bothering them whenever I asked the easiest questions. -housecleaning only EVERY OTHER DAY?!? For the amount I paid, I expect housekeeping every day. Don't greenwash the situation, they are just understaffed and/or lazy. -there was hair on my bathroom floor and in bathtub upon check-in. I didn't notice until late night on night #1 bc I came into the room, set my luggage down and left. The next day after I showered and washed my hair, they was now a lot more hair all over bathroom floor (I shed a lot). I called down to front desk to ask if someone could come just vacuum my bathroom floor and bring new towels (1 towel had someone's hair), and the guy told me NO - that I'm not due for a cleaning until tomorrow. He said someone would bring new towels but that's it. Are you kidding me?!? I've stayed in motels that had better service. --my TV sucked. Couldn't get reception. Streaming to TV didn't work. Tv turns off automatically after a few hours. -no room service option. I expect that option for the price I paid. -scratchy towels

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