According to the report, Lester will visit Wrigley Field, which is undergoing renovations, for "a formal get-together with the Cubs brass and owner Tom Ricketts."
Lester, 30, is ranked as the offseason's No. 2 free agent by SI.com's Ben Reiter.
Red Sox general manager Ben Cherington reportedly met with Lester's agent Tuesday night. Lester spent the first eight-plus seasons of his career with Boston, winning the World Series in 2007 and 2013.
Cubs president of baseball operations Theo Epstein was Boston's GM when Lester signed a six-year deal with the Red Sox in 2008.
Lester is a three-time All-Star, including an appearance this season, and pitched a no-hitter in 2008.
- Molly Geary