Staypineapple

This place is amazing! The location is killer. The beds are like clouds. I took a gummy and woke up upside down in the bed I slept so hard. 😀 it’s so clean and quiet. The staff are great and the prices can’t be beat. A must stay!

Just got back from a girls trip and this hotel was great! Clean rooms and comfy beds. Great location. The bartenders at the lobby bar are great!

We stay at StayPineapple in Chicago every time we go to the Windy City. The location is just a step away from the Art Institute, Millennium Park and some of our favorite restaurants ....like Eggys! We also love the food and bar at the Atwood right in the hotel. Sooo convenient and lovely. Choices for the adults and kids. Everyone is happy--especially with the free drinks that come with every visit. The folks at the desk are always helpful and even greet us personally when we arrive. Go on your birthday and you are treated like a queen. The building itself oozes with history because it was lovingly restored. I love staying a boutique hotel with excellent service rather than a huge multinational chain. I know I’m in Chicago. Love it!

Oh my goodness….we have lived in NW Indiana for 20 years and I don’t know how I’ve never stayed here. This is my new go to downtown staycation hotel. My bff and I had a superb stay to celebrate my 50th birthday. Kudos to Cassandra at the front desk for exceptional customer service and for making our stay amazing. The location, comfort of the beds, and sheer beauty of this historic building makes it a must for your next Windy City adventure!

Great location, comfortable rooms and wonderful employees. We had a wonderful stay at the Staypineapple. The beds are super comfortable. The water filling station in the lobby was super convenient. The staff went above and beyond and even decorated the room for my daughter's birthday! We had a wonderful time and would stay here again.

The staff go above and beyond at Staypineapple! The concierge at the check in desk was friendly and welcoming. I went to Chicago with a friend to celebrate my birthday and the staff had cupcakes and a birthday card in the room for me. The location was perfect, so many destinations downtown were walkable and we utilized the valet parking which was convenient and reasonably priced. I would definitely stay here again!

Great, friendly staff that went above and beyond for my nephew's birthday

We absolutely love it here! Currently staying and it has been a wonderful experience. The hotel is beautiful, the service has been excellent and the rooms are very comfortable. We are celebrating my partners birthday and when we got to the room, there was called champaign and a balloon. Then we got back to the hotel late last night and the door man greeted us and gave us each a bottle of water. Thought it was the nicest touch. Would highly recommend!

What a perfect trip. Booking was easy. Check in was transparent and quick. Even came with welcome drinks! We were in town to see a play and the staff went above and beyond to welcome us. The location is great and walkable. The bartender is super friendly and makes a mean handcrafted cocktail. The beds are heaven. Pineapple cookies and coffee in the afternoon. But the real star that makes this property shine is the fabulous and creative general manager, Kristin. The attention to detail is better than any “5 star” property with amenities that you really need.

We had a wonderful three-day stay at Staypineapple in Chicago! The hotel is beautiful, clean, and well-maintained. The staff truly go above and beyond to assist with any requests, which made our stay even more enjoyable. Our room was spotless and had a nice view of the street. The location is perfect - walking distance to The Bean, surrounded by great restaurants and shops, and very close to bus stops, making it super convenient for exploring downtown. We’d definitely stay here again on our next trip to Chicago!

Cassandra was exceptional! Her service at the front desk truly made our Chicago trip unforgettable. The complimentary coffee and pineapple cookies every afternoon were a delightful touch. We also loved the free drink at the bar and the unlimited sparkling or still water—fantastic amenities. This hotel is truly one of a kind.

I had the pleasure of staying at Staypineapple this past weekend for my brother's bachelor party. There was a group of about 15 of us that come and went during the course of the weekend. First off, the staff was very friendly and accommodating throughout the course of our stay. We all liked the little amenities like the free drink pass, water and coffee stations. Location-wise, it was the best possible area to stay and you were within 10-15 minutes of most of the biggest attractions. I plan on staying there again the next time I'm in Chicago.

My stay at StayPineapple was absolutely amazing!!! I booked a staycation for my birthday and when booking I commented that it was my birthday. When I arrived at my room, I was surprised to see they had decorated the room for me! So so sweet! The lobby is gorgeous and the room was pretty as well. The bed is so so comfy! I also like that they give you a refillable water bottle so that you can fill it from the fountain in the lobby and you get a coaster that you can trade in for an item from the fridge in the lobby. The location is also great, you can walk to pretty much anything you’re looking for whether that’s food, activities or shopping. Overall I’m so so happy that I stayed here. I would definitely come here again and have already recommended to my friends and family. Thank you StayPineapple!!

Very cute for girls, kids, and some people that like feminine things. Flowers, butterflies, pastels.... The rooms are tiny. We got a connecting room, which was just 2 end rooms, we closed off the door to the hallway and left both room doors open. Then we had 2 bathrooms, a living area, and the bedroom. I enjoyed the atmosphere even though it was tiny. Everything was clean and in working order. The staff were friendly and helpful. I would go back, especially if I wanted to do something with some young ladies. Nice for a slumber party away from home!

I call this location in order to book for my daughter’s birthday. Her first time stay in New York. I talked to Paul and he helped me save money by going on the official site. The have their own limited sales periodically. So I looked and there was a tax sale. I saved money and Paul was extremely patient too. I’m sure the stay will be perfect. Thanks so very much!!

We are a group of 4 women that just completed our 3rd annual stay at Staypineapple. We get a floor to ourselves since there are only 4 rooms to a floor which makes us feel pretty special! The staff is great. We love the cookies, the incredibly comfortable beds and location is so convenient.

My friend and I decided to book three nights at this hotel for our girls trip and we couldn’t be happier. The customer service was great and both Cass and Marshay were very sweet and helpful. The rooms were a bit on the smaller side but the amazing view made up for it, the area was very safe even at night with lots of restaurants and things to do all around. The hotel was beautiful and very clean. Overall, very happy with our experience and would definitely book again.

Booked for a birthday trip. The rooms are amazing, second time staying here because the first time was so great. The staff are awesome and really helpful, and really came through with early check in, and making sure the room looked great. (Decorations were from me) but they offered us wine and a little treat to make the surprise even more special. The beds are seriously the best sleep you will ever get.

Freddie was friendly and great. We really enjoyed our stay and will be back!! Thank you Staypineapple and staff!

When we go to NYC, there is no better location for us. We had another great stay for my birthday and stayed on the top floor in an iconic, fun room (albeit, small) and the staff left me a special note and treat in our room.