Why you should visit Chicago in December

There's no shortage of ways to keep the kids entertained when visiting Chicago in December. First stop: Navy Pier, where alongside the iconic Centennial Wheel and other classic fairground rides, there's also a full-on festive extravaganza in the shape of the Wintrust Winter WonderFest event. And it's really quite the spectacle – think carnival thrills, giant indoor ice-skating, towering holiday trees, and endless inflatables, and you'll be about halfway there. Step out of the cold into a massive winter playground where kids can soar on classic amusement park rides, tackle giant bounce houses, and share their wishlists with Santa inside a glowing, festive wonderland.

Also on Navy Pier, Chicago Children’s Museum is less a traditional museum and more a place for kids to interact with and discover the world around them, playing firefighters, excavating dinosaur bones, creating water-based experiments and exploring the multi-level Cloud Buster structure.

Other crowd-pleasing attractions for families seeking to escape the winter chill include the Legoland Discovery Center, the mind-bending Museum of Illusions and the mind-expanding Adler Planetarium. Hot tip: entry to these, and dozens more top Chicago tours, activities and attractions is included with Go City's Chicago pass, which can save you a stack on your sightseeing, leaving you plenty of spare cash to splash on other Chicago essentials like deep-dish pizza and rainbow ice-cream cones (guaranteed delicious even in sub-zero temperatures).

Commuting may not sound like the kind of thing that would rank highly on your Christmas vacation to-do list, but the Allstate CTA Holiday Train and Bus – running from late November through late December each year – may well change your mind.

A beloved Chicago tradition since 1992, the Holiday Train is festooned with festive decorations. Its entire exterior is also garlanded in lights, making after dark trips a must. But that's not all: Santa waves to passengers from his sleigh, complete with reindeer and Christmas trees. The train's younger sibling – the 60-foot Holiday Bus – is a winter wonderland with holiday music and, of course, another jolly Santa. That guy sure gets around. Each service integrates seamlessly with the usual Chicago bus and metro routes, so check the CTA's site for the current year's exact schedule.

Dazzling displays of holiday lights aren't difficult to find in Chicago during December. The Morton Arboretum Illumination is another must-see, running November 14, 2026 through January 2, 2027. Far from the standard Christmas lights you might expect, its 50 acres of trees are transformed into a magical world of light, color and sound.

Closer to downtown, the Magnificent Mile's seasonal lighting displays are the stuff of legend. Here, each storefront vies to outdo its neighbor, which, given there are around 450 stores, creates quite the festive spectacle. The Mile's tree-lighting festival takes place on Saturday, November 21, 2026, when some 200 Michigan Avenue trees are illuminated as part of a major parade, including Disney characters, live music and fireworks over the Chicago River.

It's easy to fill those chilly Chicago December evenings with fabulous festive fun. The Christkindlmarket in Daley Plaza has the power to bring holiday cheer to even the most curmudgeonly of Christmas scrooges. In 2026, it's open daily from November 20 to December 24. The German-themed market is the biggest in the US, with dozens of stalls, a huge Christmas tree, a nativity scene and live entertainment from dance troupes, brass bands, carolers and more. Meet up for a hot mulled wine with friends or cruise the stalls in search of unique Christmas gifts and ornaments, splendid souvenirs and a long list of edible treats, from currywurst to cookies.

Lovers of culture and tradition might also want to seek out the city’s theater spaces. The Goodman's adaptation of Charles Dickens’ A Christmas Carol  has been staged annually for half a century, whilst ballets to look out for include Tchaikovsky’s Nutcracker, set on Christmas Eve.

Chicago's New Year's Eve fireworks now happen in two spots: downtown along the Riverwalk, where the city's official countdown launches fireworks from six bridges alongside an ART on the MART projection show, and at Navy Pier, where the midnight display pairs with a ticketed ballroom party at the Aon Grand Ballroom. Or you can just watch for free from the lakefront.

Occupying the only structure still standing from the 1893 World's Columbian Exposition (or World's Fair), the Museum of Science and Industry is packed to the rafters with artifacts and objects relating to scientific discovery and human endeavor – the actual Apollo 8 command module that carried the first humans to orbit the Moon, a captured German U-boat, and a 40-foot indoor tornado you can have a go at controlling.

In December, it also hosts its celebration of Christmas Around the World and Holidays of Light – a tradition at the museum since 1942. Today it includes around 50 Christmas trees decorated by volunteers to represent seasonal traditions around the world, alongside non-Christian winter festivals such as Hanukkah, Kwanzaa and Diwali.

Further north, the Field Museum is catnip for anyone fascinated by the wider natural world. Among its most popular exhibits are Máximo – a cast of the largest dinosaur ever discovered – treasures and relics of Ancient Egypt, and the DNA Discovery Center, where windows reveal real-life scientists working to map out the genetic codes of a whole range of species.

Chicago regularly sees snow in December – the city averages around 10.8 inches for the month, enough to create an Insta-perfect wintry blanket without bringing things to a shuddering halt. Millennium Park typifies scenes across the city, with its massive Christmas tree and no-less-substantial outdoor ice rink. Sightseers, rejoice: the McCormick Tribune Ice Rink sits in the shadow of another of Chicago's must-see modern icons – the mirror-like sculpture Cloud Gate by Anish Kapoor, better known to most locals as "The Bean."

For dreamy vistas from higher up, look no further than the Willis Tower. An elevator ride of under a minute zips you to the ear-popping height of 1,353 feet, where this iconic tower's 103rd floor Skydeck promises unrivalled views of the city by day and night, taking in sights such as the Magnificent Mile and Lake Michigan. On a clear day, views extend across four different states: Illinois, Indiana, Michigan and Wisconsin. Sure, you won't see much in the middle of a Midwest blizzard, but at least you'll be warm in there.