How to Have the Perfect Holiday Vacation in Chicago

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If you're heading to the windy city this December, here's how to embrace Chicago's holiday spirit.

Chi-town is a particularly cozy town to visit to ring in the holiday season. The city in the winter is chilly as can be, but the Windy City is picturesque in the snow, as are their numerous holiday installations. Beyond that, the city is a wonderful food destination to keep foodies occupied, and it's home to some of the best museums in the U.S.. If you’re visiting Chicago this winter, don’t miss these seasonal spectacles:

Go ice skating at Millennium Park


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McCormick Tribune Ice Rink in Millenium Park is free to the public each year. The seasonal ice rink is open from mid-November until March, weather permitting. Skate rentals run from $13 to $15. If the crowds are too much at McCormick Tribune Ice Rink, you can also visit the adjacent Maggie Daley skating ribbon, which also has free admission and charts a scenic urban skating route with views of the snow-covered trees and skyline.

Stop in at The Second City for their Best of the Holidays Show

There are few things more quintessentially Chicago than seeing a show at The Second City. Some of the best comedic talent of our generation comes out of Second City, which is why stopping by for a show is a must while in Chicago. Their Best of the Holidays show is a compilation of their favorite holiday sketches of the last few years—and Second City “guarantee(s) yule laugh a whole latke.”

See Joffrey Ballet’s “The Nutcracker”


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Taking your family to “The Nutcracker” is an extra-special holiday tradition, which you can continue in Chicago even if you’re spending the holidays there for the first time. Joffrey Ballet performs “The Nutcracker” each year at Auditorium Theatre of Roosevelt University from late November through the end of December. You can also treat your family to Nutcracker Teas, which Joffrey’s Ballet hosts in conjunction with the JW Marriott Chicago.

Visit the Great Tree and holiday windows at Macy’s State Street


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Macy’s State Street is known throughout the country for its stunning holiday window displays. Their displays capitalize on nostalgia, bringing in storybook or animated characters from shoppers’ youth. Inside Macy’s, you’ll find their Great Tree, which towers at almost 50 feet. Book lunch at The Walnut Room, the restaurant inside Macy’s State Street—you’ll have a full view of the Great Tree from the restaurant.

Experience the Christmas Tree Lighting at Millennium Park


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The City of Chicago Christmas Tree Lighting takes place once a year, typically in late November to kick off the holiday season. The Millennium Park fest features live music, and of course, Santa Claus makes an appearance to welcome the season. If you miss the free tree lighting event, the tree stays up through December and is worth a visit when you’re in town.

Roam through ZooLights at Lincoln Park Zoo

Running from late November until early January, the ZooLights at Lincoln Park Zoo are a (free) wintertime spectacle. An annual tradition that started in the 1980s, the Lincoln Park Zoo is illuminated by no fewer than 2.5 million lights. Geared toward families—both visiting and local—Santa spends time at the market in December to pose for pictures. There’s also live ice sculpture carving on the weekends, and you can nosh on treats and much-needed hot beverages from ZooLights’ vendors.

Support student artists at Millennium Park Holiday Art Market

Highlighting student artists, the Millennium Park Holiday Market opens for one weekend (Friday through Sunday) in late November. It’s a chance for the students to showcase—and monetize—their art, be it jewelry, prints, sculpture, or paintings. The wares of these up-and-coming artists are unique and in the season of giving, it’s a great opportunity to support the work of Chicago students.

Stroll through Illumination: Tree Lights at The Morton Arboretum

Wandering the mile-long paved path through Illumination: Tree Lights at The Morton Arboretum is one of the most romantic Chicago winter traditions. The interactive light displays fuse music, color, and natural beauty. As if the snow-laden pine trees weren’t enticing enough, the light design only enhances their beauty. And of course, the arboretum’s bonfire where you can warm your hands and roast marshmallows sweetens the entire experience.

Shop at Christkindlmarket


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A traditional German-style market, Chicago’s Christkindlmarket serves all the pretzels, bratwursts, and spiced wine you could hope for. The open-air market has been running for nearly 15 years. It may not be warm, but the food vendors are reliably delicious and the shopping is good. If you’re coming as a family, be sure to bring your children by the market’s Kinder Club.

Where to Stay

Stay in the Fulton Market District at The Hoxton, Chicago, newly opened as of spring 2019. Cozy up in their industrial and mid-century-mod-inspired rooms, and be sure to stop by their high-end bar, Lazy Bird for a craft cocktail.