1. If you happened to be in Chicago for just one day in winter months bus sightseeing tour should be at the top the list of things to do in Chicago in winter. Take a sightseeing tour, and learn about the rich history of Chicago. Many tours offer heated buses for this event, and are held in all but the very worst weather.

2. One of the top 10 things to do in Chicago in the winter is to pay a visit to the world famous Macy’s Department Store on State Street. This twelve story building of luxurious shopping is also a historical landmark—first constructed in 1892 and restored in 1992. Those interested in its historical value can take in Macy’s on State Street in order to see the massive, seven-ton clocks originally installed in 1902, the Tiffany glass ceiling, or the “Lost Fountain” (constructed in 1992 after plans from 1892 that were never completed). Those wanting to visit the store itself can work their up twelve floors of premium shopping including fashion, wine and dining. Elaborate window displays and scenes which are animated make this area a big attraction in the winter months before and during the holiday season.

3. Daley Plaza, formerly the Civic Center, has become a hub for Chicago’s diverse culture and color. The thirty one-storied building is the site of dozens of ethnic festivals and events unique to Chicago, along with the city’s holiday celebrations. First opened in 1965, the Daley Plaza building is a historic landmark and features a titanic sculpture by cultural icon Pablo Picasso. Weekdays at noon “Under the Picasso” features performances by local groups free to the public. One of the most popular winter things to do in downtown Chicago is to visit Daley Plaza for ice skating. The frigid winter temperatures make ideal conditions for ice skating, and at this location there is no charge to use the ice.

4. Daley Plaza plays a role in another of the top 10 things to do in Chicago during winter, and this is the annual Christkindlmarket, which is a traditional German Christmas market. Every year during the holidays the mythical Christkindl (a magical, fairy-like being from German-speaking nations) arrives to open the ceremonies of the Christkindlmarket in Chicago. The Christkindlmarket is a vibrant celebration of German-speaking culture and the holiday season, which takes its roots from original celebration in Nuremburg, Germany which first began in 1545. Chicago’s version of the celebration has been a holiday tradition since 1996, taking place between Thanksgiving and Christmas day. Visitors can shop for one of a kind gifts, and enjoy traditional German music and food. This gathering of good cheer is among the best things to do in Chicago during the holidays.

5. Millennium Park makes the list of top 10 things to do in Chicago at any time of the year. Millennium Park’s number of visitors being beaten only by the Navy Pier makes it consistently among the top 10 things to do in Chicago. The 24.5 acre park is located near Chicago’s Loop, near the Lake Michigan shoreline. Millennium Park is far more than just a park but a collection of stunning, modern art and architecture, along with a center for culture. Famous architects and artists from around the world contributed to its design, with such pieces as the Pritzker Pavilion, the Cloud Gate, the Crown Fountain, and the historically inspired Wrigley Square. Its central location and multitude of hosted activities and structures bring an estimated four million visitors each year. In winter there is a free ice skating rink, as well as a large park to walk through and explore. This park turns into a winter wonderland once the first snows of the season hit.

6. A popular pastime in the colder months in Chicago is to stop by the Ritz-Carlton Chicago for a formal afternoon tea. The setting and elegance can make this a very entertaining and enjoyable event, and the hotel itself is a big part of the history of the city. Ritz-Carlton Chicago, is one of the most highly reviewed luxury hotels in Chicago. Perched atop Water Tower Place, the Ritz-Carlton Chicago offers premium accommodations, furnished in elegant design and facing the breathtaking view of Lake Michigan. Also available are a full spa, fine dining, and highly-rated service. A short elevator ride takes guests into Water Tower Place for shopping, and the Ritz-Carlton Chicago hotel is within walking distance of many other Chicago top attractions including the Navy Pier, the Hancock Observatory, Millennium Park and the Museum of Contemporary Art.

7. A visit to one of the Chicago museums can be a terrific way to spend a blustery winter day. This would be considered the off season, and there are not many crowds at this time of year, so you can really enjoy everything offered without feeling rushed.

8. One of the best things to do in Chicago in winter with kids is to take a horse drawn carriage ride. While this is usually thought of as a romantic experience, children of all ages will enjoy the ride and adventure immensely.

9. For romantic things to do in Chicago why not enjoy dinner and a show? Chicago tops the list of US cities both in fine dining establishments and in the local theater scene. No matter what your tastes are there are restaurants and shows that are perfect.

10. Any list of top 10 things to do in Chicago in the colder months would not be complete without including the experience of enjoying a package of warm roasted chestnuts from a street vendor.