The 8 Best Hotels in Chicago (Updated 2025)
"Located in the Loop inside a landmarked historic building with beautiful mahogany-lined walls and furniture, I found Staypineapple fun and cozy. Rooms are on the smaller side but have everything you need: extra-fluffy duvets, oversized pillows, soft robes, blackout curtains, huge towels, Keurig coffee/tea makers, and unlimited bottled water. I received a free welcome drink at the attached bar/restaurant, which serves great food from breakfast to late evening, and there’s a fitness center and bike rentals available." - Matthew Kepnes
