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Chicago Nightlife is richly varied and impossible to capture in this sort of overview. With obvious exceptions like Second City , Supernatural Chicago and major venues, the options change constantly and many venues are very small and not well known. There are two local sources that cover the options well. The Chicago Reader is recommended for the scope of its coverage and unbiased reviews of current options. Copies of the Reader are free and are available at many bookshops and bars, one reliable central location is the Borders Books on the Corner of Michigan and Chicago avenues. The Reader also has an online site that contains much of the same information as well as informative reader submitted restaurant reviews. Another reliable site is MetroMix, which also lists current events and has very good reader submitted restaurant reviews. A welcome recent addition has been the Chicago edition of TimeOut. TimeOut is not free, but is available in most bookstore and newsstands. Much of their online content is only available to subscribers. Other specialty free papers abound covering the alternative music scene, gay/lesbian Chicago, etc. The specialty papers will give greater coverage to niche events. These can be picked up at the same places as the Reader and from paper boxes scattered around the city. When going to alternative events be prepared to travel to areas of the city that while usually safe, aren’t exactly on the normal tourist route.
The gay/lesbian scene is concentrated around North Halsted around Belmost and in a couple other locations. Great sources for these options are the Windy City Times or Gay Chicago Magazine.
Outside the clubs, Chicago also has a dizzying array of theater in which to partake. A good place to start for theater information is, once again, the Chicago Reader. Beyond that, you can check with the League of Chicago Theaters. Same day reduced price tickets can be obtained at HotTix, which has several locations around the city. The most convenient locations for tourists are in the Loop at 72 E. Randolph Street across from the Chicago Cultural Center and on North Michigan at the WaterWorks Visitor Center 163 East Pearson, at Michigan Avenue and Chicago. These tickets can be a great bargain if you’re willing to take a chance on something you wish to see popping up. They are closed on Monday, but open at 10:00 a.m on Tuesday through Saturday and at Noon on Sunday — be there when they open!
For more info about the performing arts, see the Inside Chicago: Performing Arts article