Staypineapple, An Iconic Hotel, Chicago 

Who needs run of the mill? With its whimsical approach to design and warm welcome Staypineapple promises guests a relaxed stay in a plum location – minus the high price tag. Who needs run of the mill? With its whimsical approach to design and warm welcome Staypineapple promises guests a relaxed stay in a plum location – minus the high price tag.

The coupling of an historic 19th century building with the dare-to-be-different Staypineapple brand is a curious one but, somehow, it works. Staypineapple’s playful personality is stamped all over the restored Reliance Building, from the ‘sleep with me’ pineapple-embossed pillows to the quirky art and kitsch soft furnishings. 

4 stars

Facilities

All Hotels in Chicago & Route 66