Oprah producers called Tom and cooked up a crazy plan to get his wife, Gina, from upstate New York to Chicago without letting her know where they were going. Tom surprises Gina at the school she works at and whisks her away to the airport. To keep Gina in the dark, Tom outfits her in a blindfold, headphones and a sign that reads, "My hubby is taking me on a surprise trip. Please don't tell me where I am."
At the airport, everyone from the ticket counter staff to the flight crew is in on the plan, announcing only that the plane is headed for "the mystery city." Gina thinks they're on their way to Fiji and is still in the dark when the couple lands in the Windy City. They spend the night in a hotel room stripped of anything that could give away the surprise. There are no magazines, brochures—not even a television!