Though it first came to be in Ohio, Bobtail Ice Cream is now a home-made Windy City favorite that can be found at three locations in the city, as well as at assorted restaurants and shops. But win this treat and this delicious frozen delight will be coming right to your home—Signature Sunset, Cubby Crunch, Daley Addiction, and more. You'll receive two free pints each month for a year. Woohoo!