Hanging out in a hotel lobby isn't usually a fun experience—unless it’s at the Drawing Room. This spot in the Chicago Athletic Association Hotel in the Loop has tons of Ivy League clubhouse charm. It has dark wooden paneling, comfy leather seats, tons of tables, and two ornately designed fireplaces. So whether you’re here doing work with a cup of coffee, eating a BLT on a lunch break, or just waiting for an Uber, you can at least stay warm in style.