ROOF on the Wit-- Best bar in Chicago...one of my most favorite weekends ever! If not the best! :)
"Riverboat cruises, outdoor movies in the park, rooftop bars, comedy clubs, cupcake bakeries, baseball games [are all fun places to go for dates in Chicago]" - @JenniferStraub
The famous elevator of Water Tower Place. We came at least once a month to Water Tower with mom, as kids. Ahhh, the memories.