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Windy City-Bound: NBC’s “The Tonight Show With Jay Leno” will travel to Chicago for five nights starting April 29. The road trip, planned to coincide with the all-important May ratings sweeps period, marks the first time the entire “Tonight Show” has visited the Windy City. (Leno made a solo trip there in February 1995 to tape some comedy sketches.) Meanwhile, a previously announced “Tonight Show” trip to New York, originally scheduled for this spring, will take place in November, NBC said.

On Probation: “Living Single” star Queen Latifah, whose real name is Dana Owens, was fined $810, ordered to give $2,500 to a charity and given two years’ probation by a Los Angeles judge Friday for carrying a loaded gun in her car and driving without a valid license. The actress, a Grammy-winning rap singer who survived a carjacking in New York last year in which her bodyguard was wounded, was stopped and charged with speeding Feb. 3 on the Santa Monica Freeway. She was arrested after a CHP officer allegedly found marijuana, as well as a handgun, in the driver’s side door pocket of Owens’ 1995 BMW. Owens, 25, was not in court for her scheduled arraignment Friday, but her attorney entered guilty pleas on her behalf in the two misdemeanor counts. Prosecutors had declined to file drug charges, citing insufficient evidence.

New Annual Emmy: The Academy of Television Arts & Sciences will offer a new Emmy this year for the program “that best explores social, educational or medical issues and encourages and promotes changes that help society become familiar with and effectively meet the challenge.” All shows eligible for prime-time Emmy competition--including series, single series episodes, specials, TV movies, miniseries and informational television--will be eligible for the annual honor, tentatively called the President’s Award. White House aides said Thursday that President Clinton might present the award in person at this year’s Emmys, Sept. 8 at the Pasadena Civic Auditorium. Academy President Richard H. Frank called the new award “a special distinction whose time has come: recognizing excellence in areas of social, educational and human conditions.” Frank said the President’s Award would be considered one of the “most important and prestigious Emmys.”

Other Emmy News: Entries for the 48th annual Primetime Emmy Awards are due by March 15 for programs aired between June 1, 1995, and March 15, 1996. Shows broadcast between March 16 and May 31 must be entered by April 26. Nominations will be announced July 18. Dick Clark will produce this year’s Emmy telecast on ABC. . . . ABC Entertainment President Ted Harbert and CBS Entertainment President Leslie Moonves are among six new appointees to the TV academy’s executive committee. The others are Dean Valentine, president of network television and TV animation for the Walt Disney Co.; Barry Meyer, president of Warner Bros. Television Productions; John J. Agoglia, president of NBC Enterprises; and Mark Allen Itkin, senior vice president at the William Morris Agency.