I would be remiss if I didn’t include a lot-a-bit of blues in my recommendation for late night tomfoolery in Chicago, but forget about the House of Blues and other such tourist traps. If you want to have the most authentic, carefree, and romping toe-tappingest best time from late night until very, very late night, then Kingston Mines must be your choice. This charmingly grungy, dual staged amalgamation of buildings wraps around a fun-loving, wildly diverse (in many ways) crowd. Music ping pongs between the two stages each hour, and the bars ethos of limitless energy leaves people amazed by the lateness of the early hour when all is sung and done.
Photo Credit: ©Kingston Mines