Chicago: flat, smelly, boring, polluted lake, giant south side slums, and well...its filled with boring Chicagoans....
Rio: beach, mountains, fantastic weather, thongs, clubs, drugs, booze, lots of sex, hot chicks, weed, warm oceans, slums (but those can be cordoned off by the military), and did I mention the beaches, the thongs and the chicks?? It's really no contest...