During a pre-show planning meeting with Jenna, Oprah expresses doubt that the team will be able to pull this one off. "This is the craziest thing I've ever heard," Oprah says. "How are you going to be able to get them to Chicago at exactly that time?"

Watch Jenna's meeting with Oprah

"I am feeling the pressure if this idea doesn't work," Jenna says. "Nobody's going to blame anyone more than I'm going to blame myself."