Winter isn't exactly the most popular time to take a trip to Chicago, affectionately known as the Windy City — actually for its political blowhards, but it could also be for those frigid Winter winds. But if you're willing to bundle your family up, braving the elements can be a ton of fun. Plus, during the colder months, you'll find great deals on hotels with prime locations — we're talking less than $100 for a room right on the Mag Mile, a nickname for Michigan Avenue. If shopping little girls' favorite doll store ever, seeing the stars (and dolphins and the city from 1,353 feet up), and ice skating with a view sounds like a trip your family would love, then Chicago is the place for you. Keep clicking to see Chicago's finest kid-friendly spots.