Subway: Brown, Purple (rush hrs) to Chicago(312) 335-9500 martiniranchchicago.com41.896563 -87.636229 311 W Chicago Ave (between Orleans and Franklin Sts) River North, Chicago
Mon–Fri 4pm–4am; Sat 5pm–5am (closed Sun)Average cocktail: $9
A martini hideaway? Sounds like an oxymoron, but this River North spot manages to marry the two into a union of after-work debauchery. After the nine-to-fivers roll it up on weeknights, industry folks (local bartenders and waitstaff) saddle up a martini and ride off into the dawn. On weekends, the Ranch becomes a hitching post—DJs spin house and urbanites try to make room to grind.