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Start with the experience you want, then choose the neighborhood. Downtown works well for theater, orchestral concerts and polished cocktail rooms, while River North concentrates late-night activity within walking distance of many hotels. Wicker Park and Logan Square offer a more neighborhood-scaled mix of bars, music and restaurants. Chicago's jazz and blues traditions deserve a venue selected by the night's performers, not simply by a famous name. Sports can define an evening around the United Center or a ballpark, but event traffic changes travel times. Consult official venue listings for age limits, set times, ticketing and accessibility. Map the return trip before going out, especially when a late show extends beyond frequent service. One well-chosen performance followed by a nearby drink usually creates a better night than crossing the city among disconnected venues.