Whichever moniker you prefer – The City of Big Shoulders, The Windy City, or The City That Works – and whatever draws you here – architecture, food, sports, performing arts, museums, or shopping – Chicago is one of the most iconic cities in America. Though most choose to visit during more welcoming weather, Chicago is a great way to experience Christmas.
A classic itinerary for enjoying the sights, sounds, smells, and tastes of the city during Christmas begins with a walk along Michigan Avenue to take in the Magnificent Mile. Beginning at the north end of the storied shopping district, The Magnificent Mile Lights Festival (one of the largest holiday celebrations in America) kicks off the season with one million lights just before Thanksgiving. Famous for surviving the Great Chicago Fire back in 1871, the Chicago Water Tower gives the shopping mall at Water Tower Place its name.
One of the enjoyable experiences at Water Tower other than gazing up at the majesty of John Hancock Tower is riding the escalators, taking in the decorations, and shopping while enjoying a bag of Garrett's popcorn.
Decorations lining both sides of the Mag Mile impart appropriate panache to the window shopping experience at Neiman Marcus or Saks Fifth Avenue. Finally, one reaches the famous Wrigley Building, which is no less decorated. Despite the season, it's hard for anyone not to see Chicago's varying architectural styles while strolling south across DuSable Bridge (which is also an ideal place to witness the Chicago River dyed green for St. Patrick's Day).
A few blocks further brings Millennium Park into view. It doesn't matter if it's 100 degrees or 10 degrees outside, there will always be people at the park enjoying its scenery. During Christmas, that means ice skating and getting one's picture taken in front of The Bean. The Art Institute of Chicago also contributes a dose of holiday cheer by bedecking their iconic bronze lions that stand vigil outside the entrance.
By this time, the smell of grilled bratwurst and candied nuts compels a visit over to Daley Plaza to take in the Christkindlmarket. Featuring authentic foods, crafts, and decorations from Germany, the market is best visited during the weekday to avoid crowds. But, like Chicago weather, wolfing down a plate of potato pancakes, chasing it down with a mug of gluhwein, and standing at a table while being nudged and bumped by hundreds of people in bulky winter clothing -- without spilling anything or becoming impolite! -- is a "character builder."
Another Chicago Christmastime tradition is seeing The Nutcracker performed by The Joffrey Ballet at the Auditorium Theater. For 29 years, the company told the story within the classic European context. But in 2016, the writers changed the setting to Chicago in 1892 just before the 1893 World's Columbian Exposition, making the ballet truly tailored to Chicago's unique history.
To finish off the day's experience, walking back east to State Street puts you in front of Macy's – formerly known (and still known to many Chicagoans) as Marshall Field's – where the tradition of storefront window Christmas displays continues.
Often, the "Bucket Boys" can be seen (you always hear them before you see them) playing rhythms on upturned Home Depot buckets, but jazz and blues ensembles also gather on the street to entertain passers-by. Inside, shoppers are greeted with another tradition: lavish Christmas decorations in addition to the anchor display at the Walnut Room.
According to Macy's, it is the first restaurant in a department store and the longest-running in the country. For many, whether a tourist or a local, it is the best Christmastime lunch or dinner experience they've ever had.