I've found a bunch of links to cool deal sites which should help you have a fun night out on the cheap!
Every Tuesday in October freenightoftheatre.net is offering FREE THEATRE TICKETS! There is a pretty substantial list! Check it out Here!
Here are some more Chicago area freebies (brought to you by
@ExploreChicago Tweets reminders about free museum days, free events, and free performances.
@BrokeHipster tweets free and cheap drink specials, food deals, and events in Chicago. They update daily.
@FreeChicago Tweets free events (like flu shots, concerts, etc).