The City of Chicago Office of Tourism has a thousand ideas for places go and things to do. Consult them online, at their visitor centers, or download free tours in five languages at Downloadchicagotours.com
Gay media includes: Boi Magazine, and the group of publications from Windy City Times. Grab Magazine is Chicago's gay bi-weekly magazine, with business listings, bar events and maps, plus local color.
The weekly Chicago Reader is an alternative paper with massive listings on what's happening, all over the metro area.
Online info resources include Chicago Events, the Gay & Lesbian Chamber of Commerce, NewCityChicago, and the Northalsted Business Alliance.
Toto Tours (1326 West Albion Ave; 800-565-1241) is the pioneer in gay adventure travel with twenty years of experience. They provide small group adventure travel for gay men exclusively, bringing together fellow travelers, and fostering mutual understanding with those of other cultures.