Staypineapple: Iconic Boutique Hotel in The Loop

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!

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 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!

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.

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!

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!

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.

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.

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.

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.