While it's not quite San Francisco, Chicago is a very gay-friendly city. The neighborhood commonly referred to as "Boys Town" (roughly from Belmont Ave. north to Irving Park Ave., and from Halsted St. east to the lakefront) is the center of gay nightlife -- and plenty of daytime action too. Gay and Lesbian Pride Week (tel. 773/348-8243; www.chicagopridecalendar.org), highlighted by a lively parade on the North Side, is a major event each June.
You might also want to stop by Unabridged Books, 3251 N. Broadway (tel. 773/883-9119), an excellent independent bookseller with a large lesbian and gay selection. Here, and elsewhere in the Lakeview neighborhood, you can pick up several gay publications, including the weekly Chicago Free Press (www.chicagofreepress.com) which both cover local news and entertainment. Center on Halsted (tel. 773/929-HELP, 3656 N. Halsted, www.centeronhalsted.org), a gay social service agency with counseling services, support groups, and an antiviolence project, provides referrals daily from 8am to 10pm; you can also call the main switchboard at tel. 773/472-6469 during the day.