Subway: Brown, Purple (rush hrs) to Chicago; Red to Chicago(312) 397-1961 highballlounge.com41.896026 -87.631601 738 N Clark St (between Superior St and Chicago Ave) River North, Chicago
Tue–Fri 5pm–2am; Sat 7pm–3am (closed Sun, Mon)Average cocktail: $9
An homage to the ’50s and ’60s, this second-floor lounge is furnished with midcentury modern couches, period-inspired art and a menu of highballs. The menu provides a history lesson for each cocktail (though in retrospect, we’d prefer not to know the origin of the gin-based Monkey Gland), and the subdued room is amenable to conversation. Too bad we spent most of the time discussing how bad the drinks were.