What may be second only to the North Pole, Chicago, Illinois, is one of the coldest destinations during the holiday season. Despite its frigid temperatures, the Windy City and its residents exemplify the spirit of the holidays. From its extravagant displays of light to its festive parades, Chicago is a magical destination for families from late November to early January.
Millennium Park Ice Skating
A prime activity during the holiday season in Chicago is taking the family to ice skate in downtown's Millennium Park. The McCormick Tribune Ice Rink is situated at the city's Michigan Avenue and Washington Street, and it provides skaters with unparalleled views while on the ice. During the holidays, the city is decorated in lights, and it provides a festive backdrop for its skaters. Since opening nearly a decade ago, the park sees more than 100,000 ice skaters each year. The rink is open from mid-November through mid-March, and it's also open to the public on Thanksgiving and Christmas Days.
Christkindlmarket Chicago
Since 1996, the annual Christkindlmarket has brought a taste of German holiday tradition to the Windy City. The four-week event, held from the end of November through Christmas, draws more than half a million visitors each year from around the world. The Christkindlmarket Chicago is the ideal holiday activity for families, as it provides shopping, cultural food and dining, as well as entertainment, such as ballet productions of "The Nutcracker." Admission to the open air market is free, and children and adults are able to walk throughout the market.
Polar Adventure Days
Each year, Northerly Island holds a monthly Polar Adventure Day from December through February. The family friendly day event is free of admission and provides families unparalleled winter activities. Whether visiting with the winter animals, watching an ice sculpture carving or participating in winter activities, there is no shortage of entertainment the day of the event. Children will enjoy seeing the Siberian huskies and learning about the Iditarod dog sled races. Families will have fun trying on snowshoes and using them on the island, if there has been snowfall.
Chicago Sports Fest
Hosted by the Chicago Mayor's Office of Special Events is the annual Holiday Sports Festival. The two-day event is held at McCormick Place's South and North Buildings. The December event is designed for families to engage in fun and fitness. In addition to skills and demonstration areas, children and adults are invited to become a part of the interactive exhibits, which include tumbling, jump rope, martial arts, basketball, climbing walls and fencing. Chicago sports team players also make guest appearances during the weekend event.
Santa Hustle 5K
Held at Chicago's Montrose Harbor in early December, the Santa Hustle 5K generates a crowd of Santas. As part of the race fee, runners receive Santa caps and beards; they are encouraged to don these caps and beards during the festive race. These healthy Santas follow the course in their costumes as they race throughout the city. Children and families will enjoy seeing hundreds of Santas abound during the race, keeping their naughty and nice tally in check.


