Maddux, who has helped the Rangers win back-to-back AL pennants, spent four hours on Tuesday and the entire morning on Wednesday interviewing with president of baseball operations Theo Epstein, general manager Jed Hoyer, vice president of scouting and player development Jason McLeod and assistant GM Randy Bush.
Maddux took himself out of the running for the Red Sox managerial opening on Monday, citing family reasons. He said family considerations could also take him out of the running for the Cubs job.
"We have a lot of things to think about and a lot of things to weigh," Maddux said. "Family is very important. I played for a long time and when I finished playing my kids were 10 years old and 8 years old. I said what happened? So I got into coaching right away, and we moved the family to Wisconsin. At least we were together.
"Then I went to Texas. For the first two years my wife and youngest daughter stayed in Wisconsin. My oldest daughter was with me in college in Texas. As of June my family resides together. That had not happened in three years, and that's pretty special. There does come a time when you have to stop and smell the roses. There are a lot of tough decisions that would have to be made."
Maddux said one of his first calls when he learned the Cubs were interested in talking to him was to his brother, Greg. Just to get some updated information and a bit of background on the team that might want to hire him.
"It's kind of cool to be considered," Maddux said.
"I enjoyed it, man. Pretty neat. Something I've never done before, so it was a learning experience on both ends," Maddux said. "I think I got to know them and they got to know me, see what our values are. We share a lot of values, share passion. We share the inner drive to win."
Epstein fired Mike Quade last week. The Cubs also have interviewed Phillies bench coach Pete Mackanin and Brewers hitting coach Dale Sveum. Indians bench coach Sandy Alomar Jr. is scheduled to interview on Friday.
Maddux flashed a sense of humor during a meeting with reporters. Especially when asked how he would handle the moody, one-time ace Carlos Zambrano, who was suspended for 30 days last season when he cleaned out his locker and threatened to retire shortly after giving up five homers in a game against the Braves.
"First thing you got to do is get to meet him. I heard he's a big teddy bear," Maddux said. "I might pick him up and just burp him."
Turning more serious, Maddux said several years ago he considered Zambrano to be the best pitcher in the National League with his work on the mound, in the field and at the plate, where he is a respectable hitter. "I've seen him dominate," Maddux said.
Zambrano, who is pitching winter ball, has a year left on his five-year, $91.5 million contract signed in 2007, and it's still not known if the Cubs will bring him back.
As pitching coach for the Rangers, Maddux played a key role in back-to-back World Series appearances for Texas.
The Rangers had an American League-worst 5.37 ERA in 2008, the year before Maddux arrived. They have improved each year since, including a 3.79 ERA this season that was their lowest since 1983.
Maddux's ability to get the most out of the Rangers' staff -- even after the loss of Cliff Lee from the 2010 AL championship team -- is certainly appealing to Epstein.
"Maybe it's a message, maybe it's giving guys the opportunity to perform, maybe giving them an opportunity to fail," Maddux said. "Maybe that's it, too. You don't put the weight of the world on your shoulders. You encourage guys. It's not life or death. It's win or lose, but it's not life or death. And keep it that way."
In 15 major league seasons, Maddux pitched for Philadelphia (1986-89), the Los Angeles Dodgers (1990, 1999), San Diego (1991-92), the New York Mets (1993-94), Pittsburgh (1995), Boston (1995-96), Seattle (1997), Montreal (1998-99) and Houston (2000).
The name Maddux will always resonate around Wrigley Field.
Greg Maddux's departure from the Cubs as a free agent after winning the first of his four straight Cy Young awards in 1992 is still considered one of the worst episodes in the franchise's long history of futility.
Maddux went on to star with the Braves and establish himself as one of the greatest pitchers of all-time. He returned to the Cubs in 2004 and before he was traded to the Dodgers in 2006, he got his 300th win with Chicago. He retired with 355 victories and is a shoo-in Hall of Famer when he's eligible.
Mike Maddux wouldn't go into detail but said he discussed with his brother the possibility of coaching, should he get the job. Greg Maddux was an assistant to former Cubs GM Jim Hendry and is one of the most respected pitching minds in the game.
"We talked about it, yeah. Sure did," Mike Maddux said.
Information from ESPNChicago.com's Bruce Levine and The Associated Press was used in this report.