Where does the Cubs connection come from?
NBC Los Angeles reported on October 23, 2016 that Scottie Pippen is a Chicago Cubs fan. The outlet quoted him as saying, "This city is ready for another championship." The report is the source of the Cubs link, and it is a reported fandom, not one Pippen has confirmed in an interview of his own.
The geography is the part that fits. Pippen played for the Chicago Bulls from 1987 to 1998 and later returned to the franchise, so the Cubs are a hometown team for the stretch of his career spent in Chicago. He was born in Hamburg, Arkansas, and attended Hamburg High School before playing at Central Arkansas, so the Chicago tie comes from his playing years and not from where he grew up.
What about the Chicago Blackhawks?
The Blackhawks link is thinner. NBC Chicago, writing on June 6, 2015, described "former Bulls star Scottie Pippen also voicing their support of the team." That line comes from the outlet, not from Pippen, and it is a background tie to the team, not a stated fandom of his. It is also tied to his Bulls career in the same city.
Questions people ask
What team did Scottie Pippen root for growing up?
Nothing available ties him to a favorite team in childhood; the Chicago links come from his years with the Bulls.
What is Scottie Pippen's favorite MLB team?
NBC Los Angeles reported in October 2016 that it is the Chicago Cubs, though he has not confirmed it in his own words.
Is Scottie Pippen a Blackhawks fan?
NBC Chicago reported in June 2015 that he was voicing support for the team, which makes it a background tie, not a fandom he has stated himself.