"Thanks to Lake Michigan and a lovely skyline, Chicago rooftops are very popular during the summer. But it can be exhausting dealing with the wind - everything on the table needs to be held down, and the occasional rogue balloon from someone’s “release ceremony” might interrupt your meal. Cindy’s in the Loop is a rooftop that has both indoor and outdoor tables, and both have excellent views of the city. The menu here has a lot of large-format dishes (like whole-grilled trout or platters of wagyu beef cheek), which makes it great for entertaining groups of out-of-towners who only visit when it’s warm." - adrian kane