Booker was drafted in the third round (78th overall) in the 1999 NFL Draft by the Chicago Bears. He started four of the nine games in which he played during his rookie season, catching 19 passes for 219yd and three touchdowns. He did not play in each of the first six games of the season, with his first regular season action coming on an October 24 contest against the Tampa Bay Buccaneers. Booker's first career reception occurred on November 14 against the Minnesota Vikings, when he grabbed seven passes for 134yd and two touchdowns in what was also the first start of his career. He became the first Bears rookie to register a receiving game since Willie Gault in 1983. Booker also combined with Marcus Robinson to become the 15th tandem in Bears history to record receiving games in the same contest.