Winter Activities in Chicago

Although winter routinely draws the wrath of Chicagoans and visitors alike, it also brings an abundance of joy and entertainment for all. Chicago residents, especially those at Optima Signature, are particularly fortunate, with convenient access to some of the city’s most sought-after activities and venues. Here are just a few of the many ways you can experience the best of winter in the city. 

Daytime Agenda

There is no better way to start your morning than with an invigorating walk along the lakefront, where Chicago’s crisp air will stir your senses. You’ll be dazzled by the views of a snowy Chicago skyline that showcases many of the city’s architectural achievements — including John Hancock Center, St. Regis Chicago, the Mies van der Rohe buildings at 860–880 N Lakeshore Drive and more. And the spectacular sight of towering ice chunks piling up along the Lake Michigan shoreline is not to be missed.

We recommend your morning route takes you to Millennium Park. This iconic Chicago park lights up with vibrant colors and sounds during the winter months. Don’t miss out on winter musts like taking a snowy selfie at The Bean, or popping into the Art Institute to view one of the many blockbuster exhibitions on view.

The festive drinks at JoJo’s Shake Bar
The festive drinks at JoJo’s Shake Bar

If you’re searching for a unique ice skating experience this year, make your way to the famous Peninsula Hotel, which is only a few blocks north of Optima Signature. Explore the hotel’s exceptional sky rink for the special experience of skating in the clouds of downtown Chicago, surrounded by the city’s skyscrapers and inspiring views. The one-of-a-kind experience is a kid-friendly activity too. If you bring your child, the proceeds for admission ($20 for adults and $10 for children) are donated to two Chicago children’s charities: Ann & Robert H. Lurie Children’s Hospital of Chicago and Hephzibah Children’s Association.

Once you’re ready for a warm-up, head a few blocks North and indulge in a Biggie Shake or a gourmet Hot Chocolate from JoJo’s Shake Bar. You can’t go wrong with any of their famous, over-the-top specialty drinks that are essential to experiencing the best of Chicago’s winter season. 

Trees are illuminated with vibrant colors at The Lincoln Park ZooLights experience
Trees are illuminated with vibrant colors at The Lincoln Park ZooLights experience

Evening Agenda

The fun doesn’t end once the sun goes down! There are countless evening winter activities throughout the city that you can’t miss this year. 

Of course, we can’t go without mentioning the legendary Lincoln Park Zoo Lights. Brighten up your night by strolling through the hundreds of holiday light displays. This year, the exhibition introduces new features, including an alluring Enchanted Forest experience and an 18-foot Christmas tree! The beloved holiday tradition runs until the beginning of January and costs $5 for admission, excluding Mondays and Tuesdays, which are free for visitors.

The Nutcracker at the Joffrey Ballet, Photo courtesy of Cheryl Mann
The Nutcracker at the Joffrey Ballet, Photo courtesy of Cheryl Mann

Finally, cap your night by seeing a production of The Nutcracker at the Joffrey Ballet. This is a Chicago must, as it celebrates the culture and history of the city. During the performance you’ll be transported into another world, serenaded by the orchestra’s performance of Tchaikovsky and wowed by the dancers’ performances. Tickets can be found on their website and the production runs from December 4–26, 2021. 

Chicago’s winter can feel long, so while you can, fill your days and nights with enthralling seasonal activities to brighten your spirit. We promise you’ll feel the magic.

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