Rob Ford told the Toronto Sun he plans to attend Sunday's Academy Awards in Los Angeles, Calif.
The paper says the mayor's trip south of the border will also include an appearance on the late-night talk show Jimmy Kimmel Live.
Ford, who is running for re-election, has been mired in scandal since two media outlets reported last year they had seen a video that showed him smoking what appeared to be crack cocaine.
While he initially denied the allegations, Ford later admitted he has smoked crack cocaine, likely during what he called one of his "drunken stupors."
Ford told the Sun he had no problems crossing the border and everyone has been "friendly."
A photo posted to the mayor's Twitter account seemed to show him at Chicago's O'Hare airport. The image was retweeted by Kimmel's account.