funky buddah lounge is close as it get. look online to see whats going on that night,
http://www.funkybuddha.com/
also if you into the open mic mixed crowd try subterranean
http://subt.net/
hate to say it but chicago dont really cater to the hip hop scene, its not alot of money in it, you might be able to catch a nice open mic spot full of underground artist, but you won't find alot of females or normal black people there.
mostly the back pack nerdy kick push crowd.