c) In a crowd of weekend adventurers in West Loop or Lincoln Park?. b) At a Sunday brunch in Wicker Park with your married friends and their kids?. Speed Dating Chicago with CitySwoon: Relaxed, Friendly and Fun Question: Where are Chicago's most eligible single people (i.e., YOU), most likely to meet and fall in love?Ī) Out with colleagues at Friday night after-work drinks in the vibrant River North?