Chicago’s Best Winter Events

December 3rd, 2015 by: relatedchicago

Related Realty Winter BannerChicago is one of those perpetually vibrant cities that thrive through all the seasons. Sure, the winters here are often cold and snowy, but that doesn’t mean hibernation is the only option. Far from it. An array of festivals and events bring each season to life in the Windy City, and winter is no exception. What follows are some of our favorite snow boot- and scarf-worthy events:

Winter WonderFest

Currently in its 15th year, Winter WonderFest is an absolutely massive holiday festival that runs from December 5th through January 10th at Navy Pier. The festival spans 170,000 square feet and features theme park rides – including a 50-foot Ferris wheel – games, obstacle courses, food vendors, climbing walls, a mini golf course, and nearly anything else one could imagine. A forest of hundreds of decorated Christmas trees contain more than 25,000 ornaments hung from a mile of wire. You can also skate on the Blackhawks ice rink, go snow tubing, or head to the Claus residence to hang with Santa and his elves. The entire space at Winter WonderFest is a venerable holiday mecca for all ages can enjoy—as well as a nice escape from the cold. Details here.


Christkindlmarket is the wildly acclaimed Chicago version of the German and European cultural and holiday festival. Scheduled to run from November 20th to December 23rd this year, the absolutely massive event is the Windy City’s largest open-air festival and, undeniably, its most popular, drawing more than 1 million visitors. Throughout the festival, the entire outdoor expanse of Daley Plaza is transformed into a quaint European village with nutcrackers and Christmas trees situated between traditional German food stands and art vendors. Attending Christkindlmarket is a transportive experience—within minutes, many forget they’re in the middle of a massive metropolis. It’s a phenomenal festival for all ages. Details here.

Chicago SketchFest

Coming up on its 16th year, this renowned sketch comedy festival is one of the premier winter attractions in Chicago. The largest festival of its kind on the planet, SketchFest consistently features the best-of-the-best sketch and improv performers from across the country. Chicago has been known as a sketch comedy haven for decades now as improv clubs like Second City and iO have grown to become comedy institutions and breeding grounds for future Saturday Night Live stars. More than 185 shows will occur during the eight-day stretch of the 2016 festival, which is scheduled to run January 7-17. This is the place to see the next Tina Fey, Amy Poehler, Steve Carell, Stephen Colbert, or Vince Vaughn—and to occasionally see one of these celebrities themselves. Check the SketchFest website for more information.

Millennium Park Ice Rink

Going for a skate at the McCormick Tribune Ice Rink in Millennium Park is just one of those Chicago winter rites of passage. The rink is beautiful and the atmosphere is second to none. The massive surface—which opens to the public in mid-November each year—is lit up and bordered by trees adorned with sparkling lights as the towering Chicago skyline paints the background. The entire scene is decidedly picturesque. It’s not often that one gets the opportunity to skate outside in the middle of a large city, and yet the simplicity of the experience is truly unique. This winter, pick a sunny day, prepare to brave the cold, and head out for a skate.

Throughout every season, Chicago is a bustling metropolis that’s brimming with activity. As the Windy City grows more dynamic with each passing year, Chicago real estate companies like Related Realty remain vital players in its vibrant development.


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