Winter in Chicago: Our Favorite Things

Pioneer Court on Michigan Avenue in Chicago

Chicago winters get a bad rap. Yes, it is cold and often snowy, but it’s also a magical time in the city—especially in December when the summer crowds are gone, and the city puts its best holiday foot forward. Most GNP Realty employees grew up in Chicago or neighboring suburbs, so we don’t let the cold stop us from enjoying winter in our favorite city.

In that spirit, we asked our team to share some of their favorite winter activities—many of which they’ve enjoyed since they were kids. Following is a list of what they shared. Whether you live in the area or plan to visit, consider adding one or more of these activities to your winter calendar.

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Enjoy the lights

N. Michigan Ave. stands up to New York City anytime with its sparkling white lights lit in November during the annual Magnificent Mile Lights Festival, for which our building enjoys a strategic location. Animal lovers should head north for ZooLights at Lincoln Park Zoo. Great for kids of all ages, this family tradition supports the zoo’s animal care and conservation work and helps to keep the zoo free for the rest of the year.

Shop for gifts (or yourself)!

While Marshall Field’s department store is long gone, Macy’s continues its time-honored traditions of the 45-foot decorated “Great Tree” (in its 115th year!) in the Walnut Room and festive State St. window displays. If craft gifts are more to your liking, check out the Christkindlmarket in the loop’s Daley Plaza, where you’ll find vendors selling traditional German crafts and treats. (Be sure to enjoy a cup of hot mulled wine!)

Warm up at a museum

If you need a break from the cold, the Museum of Science and Industry is hosting its annual Christmas Around the World and Holidays of Lights. This 80-year tradition that started with a single tree in 1942, newly decorated each day for 12 days to represent the WWII allied countries fighting alongside the US, now features 50+ trees highlighting numerous countries and cultures. Art lovers should visit the world-renown Art Institute of Chicago, where the famous two-ton bronze lions (recently cleaned and refurbished after 21 years) stand guard, decked out in their holiday wreaths.

Lace-up some skates

Enjoy amazing downtown views from the Millennium Park ice rink. It’s free if you bring your own skates but reserve a ticket online in advance. The nearby Skating Ribbon at Maggie Daley Park offers a different experience—a quarter-mile undulating ice track within a grove of evergreen trees. (For history buffs: The rink sits on the exact spot of the first Ferris wheel, erected for the 1893 World’s Fair.) Both offer skate rental and are open through early March when the crowds have dispersed a bit after the holidays. (Take a selfie at “The Bean” while you’re there!) Get above the crowds at The Peninsula Sky Rink. Located above Michigan Ave., the synthetic rink is Chicago’s only hotel skating rink.

Blackhawks game

If you prefer to watch people on skates, get a ticket for a Chicago Blackhawks game. Our folks are big Chicago sports fans, but the Blackhawks reign! We were thrilled to have the Stanley Cup grace our building following the 2013 win! If hockey’s not your game, try the Bulls or Bears.

See a show

Chicago is known for its live theatre. Enjoy annual favorites such as A Christmas Carol at the Goodman and Joffrey Ballet’s production of The Nutcracker at the Lyric. Visit for a complete list of holiday shows in the area.

New traditions

Winter is a great time of year to start a new Chicago tradition. Here are some suggestions from our staff:

  • Curl up at the Gwen. You don’t have to be an overnight guest at the Gwen Hotel to use the small iceless curling rink on the fifth-floor rooftop bar. Book a table and enjoy a signature curling cocktail between “ends” of curling.
  • Pop-up experience. We recently helped a client fill a vacant space with a pop-up experience Roar on Rush, where you can step back in time to a 1920s Speakeasy.
  • Candlelit concerts. Choose from unique Chicago venues, hosting live musical performances illuminated by candlelight.
  • Take a ride on the CTA holiday train (or bus). There is no better way to add merriment to your commute than to hop on the CTA’s holiday train or bus—decorated with seasonal lights and images. If you’re not lucky enough to happen on one, check out the online schedule.

Whether you prefer the warmth of the indoors or love to embrace the cold and beauty of the city decked out for the season, our favorite winter things in Chicago are just a tiny slice of what the city offers. The GNP Realty Partners team wishes you and your family a joyous winter—and great fun discovering your favorite Chicago winter activities!