Staypineapple, An Iconic Hotel, The Loop

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Nice room with a view of the Chicago theater & Macy's in the old Marshall Field building. Super convenient to take buses or El trains. We were happy that we came from O'Hare and were able to take 1 train and be within a block of the hotel. When we checked in, we were supposed to get a "Welcome drink", but they told us they were out of them. Huh? The hotel bar was 20 ft. away. They offered us one for the next night, which was nice. I got a beer that the hotel bar offers. They had 2 bottles of wine at the reception desk that I guess the bar doesn't sell. It was all kind of silly. Pineapple theme is a gimmick but it's cute I guess. Great historic building with beautiful architectural details - that I really liked. BEST, fluffiest towels ever! Also, we had drinks at the bar that first night & loved our bartender, Gabe. He made some amazing espresso martinis that had some ancho chili oil in them! Gave a subtle heat - really interesting & delicious. Overall it was a nice stay & great location!

We loved our stay at StayPineapple. The name is strange but the hotel is awesome. Very historic but still very clean and updated rooms. In the heart of Chicago we will definitely stay here again for sure.

Great historic building expertly converted to an iconic hotel. As an architect I was thrilled to stay in the historic Reliance building.

Great location with easy access to everything. Spacious rooms and a great staff. Rates were very good.

It was nice and in the perfect location.

We had a wonderful stay at Staypineapple Chicago! The entire hotel was incredibly clean and well-maintained from the lobby to the room. The amenities are fantastic—we loved the quirky touches, the incredibly comfortable beds, and the fun afternoon treats. A huge thank you to the staff, who were consistently helpful, welcoming, and quick to assist with anything we needed. One big tip for future travelers: The hotel charges $75 for valet parking. My recommendation to everyone is to download the ParkWhiz app and check for parking nearby ahead of time instead. You will save a ton of money!

Great room, lovely environment. Close to all forms of transportation. We used the L train, and bus and foot to get around. Free sparkling water refills kept us hydrated.

This is our third stay at this property. The location cannot be beat!!! Central to everything including the red line if you plan to use the train. Make sure you get your Welcome drink, pineapple sugar cookies, and reusable water bottle from the room. The staff is always wonderful. The iconic Macy’s is across the street and you are steps from Goddess and the Baker…yum.

Location. Close to everything.

Great stay great location great staff.