2. Chicago, Illinois

The Art Institute of Chicago at Christmas

Although Chicago is a popular tourist destination during the summer months due to the beautiful lakefront path, wonderful museums,  and wonderful architecture, there is no shortage of winter fun in store. If you can brave the chilly temps, you can have a fantastic time enjoying the many wonderful seasonal events and activities in and around the city. Check out a few favorites below.

Top winter activities in Chicago

*Ice skating at the McCormick Tribune Rink at Millennium Park

Millennium Park ice rink in Chicago, Illinois

Every winter, Millennium Park is transformed into a winter wonderland with the annual opening of the McCormick Tribune Ice rink and the return of carolers on Friday nights in front of the famous Cloud Gate Sculpture. As you test out your skating skills, you will be treated to views of some of the finest architecture in city.

*Holiday shopping on North Michigan Avenue

A holiday season in Chicago would not be complete without walking along the Magnificent Mile, one of the premier shopping destinations in the country. The season kicks off early in November with the annual Magnificent Mile Light Festival, featuring a parade, live performances, and a special fireworks show.

*Holiday Magic at Brookfield Zoo

Brookfield Zoo, located in the Chicago suburbs, offers one of the best holiday extravaganzas in the area. Along with taking in the sights of over 1 million LED lights, you will also be able to watch live ice carving demonstrations, listen to carolers, enjoy hot treats, take a special holiday tram ride, and visit indoor exhibits.

*Zoo Lights at Lincoln Park Zoo

Lincoln Park Zoo Lights in Chicago

Chicago other zoo, Lincoln Park, is located not too far from downtown. It is much smaller than Brookfield, but has a fantastic holiday light display (better than Brookfield, in my opinion). The free annual Zoo Lights festival is truly one of a kind. Grab a spiced wine or hot cocoa and enjoy strolling around while taking in the colorful display – not a single tree is left undecorated! You will also find an amazing synchronized light show, ice carvings, and ice skating on the lineup.

*Chriskindlmarket in downtown Chicago

Chicago Christmas Tree at Daley Plaza in Chicago

This seasonal outdoor market in Chicago is a popular annual event, with guests coming from around the world. Here you will find many vendors, including several offering the most beautiful German ornaments, along with a selection of German food and drinks.

*Macy’s Holiday windows and shopping on State Street

Macy's holiday window displays in Chicago

One of Chicago’s most timeless holiday activities is a visit to State Street to view the festive Macy’s holiday windows. Each year a new story is told. Be sure to stop by for lunch at The Walnut Room, located on the 7th floor of Macy’s, for a holiday lunch next to the grand 45 foot tall tree.