Cubs president of baseball operations Theo Epstein was hopeful on Wednesday that the team would re-sign Wood, who has spent 12 of his 14 major league seasons with the Cubs.
"We said all along we want to get this done," Epstein said. "We have a world of respect for Kerry and this should be a no-brainer, but sometimes during the winter things get a little more complicated. We have a lot of things going for us. Namely we want Kerry to be here. We surely want him to be here. And he sincerely wants to be a Cub. So if we can't figure this one out, something is wrong. I'll stand by that."
Wood's representatives have talked with several teams, including the Philadelphia Phillies, Boston Red Sox and Detroit Tigers. Wood told NBC-5 Chicago on Sunday that he would make a decision by Friday. The Cubs' traveling caravan started Wednesday with team officials and players leading up to the beginning of the Cubs Convention on Friday.
Cubs general manager Jed Hoyer said Tuesday that the Cubs offered Wood a "substantial raise," and hoped to get a deal done soon.
Wood signed a $1.5 million deal with the Cubs last season, leaving a two-year, $10 million contract offer from the Chicago White Sox and a one-year, $5 million offer from the Boston Red Sox on the table.
Wood and then-Cubs GM Jim Hendry agreed to the under-market deal in order to aid the team, which was cutting payroll, and re-establish Wood's relationship with the Cubs.
Before re-signing last season, Wood met with team chairman Tom Ricketts for their first ever face-to-face meeting, during which Ricketts told Wood that after his career ends he'll have a job with the Cubs for as long as he wants. According to MLB sources, Ricketts didn't go into detail as to what the pitcher would be doing; however, Wood left the meeting feeling that he'd be an ambassador for the team in some capacity when he retired.
Wood, the Cubs' No. 1 pick in the 1995 June draft, earned rookie of the year honors in 1998 and spent the first 11 years of his career in the organization. He punctuated his rookie season with 20 strikeouts against the Houston Astros on May 6.
Wood was 3-5 with a 3.35 ERA in 55 games for the Cubs last season. He suffered a torn meniscus in his left knee in mid-September and had successful arthroscopic surgery on Sept. 30.
Bruce Levine covers baseball for ESPNChicago.com and ESPN 1000.