The interview took place on top of a double decker bus with the back drop of the city and the Magnificent Mile. Oprah talked about everything from Chicago's Olympic bid to how her first talk show in the Windy City inspired Tuesday's kickoff party.
"It was called AM Chicago. My very first interview show was on State Street. Those were some of the best years, best times when I was down literally with the people. We started talking, 24 years, what are you going to do and we said we gotta kick it up a notch," said Oprah.
"I have some wonderful sponsors happy to have them we have to do our part paying back the city. But it's all worth it," said Oprah when asked how much the event cost.
The 'queen of talk' says she understands the magnitude of the season kickoff celebration. But she also says the city that works still appreciates the biggest block party on Mag Mile.
"This city has never failed me. I could cry when I think about this city. This is my favorite city in the world," said Oprah.
And Oprah wanted to showcase her city globally with the hopes that just maybe it might influence the International Olympic Committee when they make their final decision on the host city for the 2016 Summer Games.
"I do hope the Olympic Committee is watching because seriously I just don't know a of a cleaner friendlier more sophisticated, cosmopolitan has everything city than this city. If they are watching, I would be very happy about that," said Oprah.
Oprah's public support for Chicago's bid to host the 2016 Summer Games was evident when she kicked off her new season last year with the medalists from the Beijing Summer Games.
"I'm not sure yet but if I'm needed there, that's what I will do," said Oprah when asked if she will go to Copenhagen on October 2nd when the IOC announces who will get the Games. "I haven't talked to the president. He has enough going on without me intervening."
The president's home city and the headquarters for the Oprah Winfrey show make Chicago one of the biggest tourists attractions in the country.
"Lots of people come to the city to see the show just to see the Oprah Winfrey show and they are all excited...I think the more we can do that the better for all of us in the city," said Oprah.
Oprah also talked about the only time she was nervous in her career when she interviewed the late Michael Jackson back in 1993. And she says her interview with Whitney Houston was the best interview she has ever done.
Oprah also told ABC7 that she has to make the decision this year as to whether or not she will continue the Oprah show past the 2011 season.