Chicago

This is my adopted hometown and I love it. It is quite possibly one of the best cities in the world. And it is chock full of stuff for gays and lesbians.
There are three gay weeklies in the city. The Windy City Times has the best news coverage of both national and local gay news. It's also the most professional looking. It's available throughout the city. Outlines is another weekly that has the best enterainment coverage. It also has a several sister publications covery the black gay community, latin gay community, business and the bars. They also produce a yearly resource guide. Gay Chicago is a weekly magazine that has the best and most comprehensive listings for bars, businesses and groups for the Chicago metro area. Check them all out. All of them together can tell you all you need to know about the gay life in Chicago.
Chicago is also one of the few cities with gay radio. LesBiGay Radio broadcasts weekday afternoons on two AM radio stations through out the city.They also broadcast over the Internet.
You can also look up the Chicago Gay and Lesbian Bar List. This is an incredibly comprehensive website with a list of bars and other establishments in Chicago and the suburbs. The place to go to see what's going on in Chicago.
For more general stuff, there are other resources. WBEZ is Chicago's National Public Radio station. They regularly have announcements on theatre and other events in the city. Chicago also has two alternative weeklies (this is a huge newspaper town). New City and the Reader. Both have massive listings of bars, theatre, concerts and anything else in town. The Reader is easiest to find on the North Side and downtown and New City can be found anywhere.
If you prefer the old standby, Chicago still has two competing daily newspapers. The Chicago Tribune and the Chicago Sun-Times. They also have listings and reviews.
A few other things of interest, the Gerber/Hart Library is a major gay and lesbian library. They have all sorts of stuff about gay and lesbian history in Chicago.
There is also a large Chicago Gay & Lesbian Chamber of Commerce. If you want to find a gay-owned business, this is the place to go.
For more on Chicago and Illinois overall, check out the Illinois Queer Resource Directory.