A Guide to Winter in Chicago

November 22, 2017 | By Luxury Living Chicago Team
Reading Time: 7 Minutes

Luxury Living’s Guide to Winter in Chicago:

If Chicago is known for one thing, it’s our winters. While definitely cold and snowy, winters in Chicago are also filled with fun holiday events to keep you, your family, and your friends as cheerful as the mulled wine you’re sipping.

As Lake Michigan begins to freeze, downtown lights up with holiday excitement and hosts multiple tree-lighting ceremonies, markets, ice skating rinks, and musical acts throughout the winter season.

Since there are so many activities to do in the winter, we’ve compiled an organized list to show all of the amazing opportunities winters in Chicago holds.


The Best Holiday Events in Chicago

The holiday season is an exciting time in Chicago filled with parades, lights, and best of all, holiday food. The Windy City is packed with many different events that cater to everyone’s holiday bucket list.

From holiday pop-up bars to meticulously decorated restaurants to Christmas markets, the holiday cheer can easily be felt. The season is celebrated through holiday trains, ZooLights at Lincoln Park Zoo, winter-themed festivals, and holiday parades throughout the city.

Anything that you can imagine for the holidays, Chicago’s probably already doing. Must-sees include Christkindlmarket, Magnificent Mile Lights Festival,  and Navy Pier’s Winter Wonderfest. Don’t forget to catch the Holiday “L” train and ride with Santa!


Take a Tour of Chicago Christmas Lights

Photo courtesy of Lincoln Park Zoo

The city literally lights up during November and December. There are many places in Chicago with holiday lights and events that are the perfect place to snap a picture.

Watch Michigan Avenue come to life with over a million lights at The Magnificent Mile Lights Festival on November 18. ZooLights in Lincoln Park is another can’t miss lighting events as well as taking a stroll down State Street and enjoy the beautiful Macy’s holiday display.

Christmas Around the World at The Museum of Science and Industry puts up a display of lights and decorations from around the world to appreciate how other cultures around the globe celebrate the holidays and bring multiple cultures together through the unity of one displace.

Additionally, taking a drive into the suburbs and seeing the houses decorated with lights and decoration for the holidays gives you the perfect excuse to post two Instagrams in one day.


Get in the Holiday Spirit at the Chicago Tree Lighting 

Photo courtesy of TimeOut Chicago

Tree Lighting is a classic event in Chicago during the holiday season and can’t be missed. Downtown Chicago has many tree lighting ceremonies and displays throughout the holiday season that draw excited crowds.

The City of Chicago presents an official Christmas Tree Lighting Ceremony in Millennium Park and features at 65-foot tall tree and Christmas entertainment. The city accepts nominations for the tree beginning in September with the following guidelines: the tree must be a spruce or a fur, at least 55 feet tall, and located within 100 miles.

The Magnificent Mile Lights Festival lights up all 250 trees along Michigan Avenue at once. In addition to the lights, an exciting parade with festive floats and multiple musical performances throughout the event.

Macy’s on State Street is the perfect place to walk past to see elaborate and dazzling Christmas window displays while strolling near Millennium Park.

Other great Christmas displays include Christmas Around the World at the Museum of Science and Industry, Zoo Lights at Lincoln Park Zoo, Winter Wonderfest at Navy Pier, and Christkindlmarket


Where to Go Ice Skating in Downtown Chicago

Now that we talked about all of the lights in Downtown Chicago, it’s time to delve into one of the best winter activities: ice skating. For beginning or even the most experienced skaters, ice skating is a fun activity for everyone to enjoy.

Photo courtesy of Choose Chicago

Ice skating is a great way to stay active and warm in the chilly weather while having a fun experience embracing winter. There are many different options ice skating throughout Chicago.

Outdoor skating options are more common in the downtown area and if you want to skate indoors you have to venture a bit further north out of the city to McFetridge Sports Center.

The McCormick Tribune Ice Rink is an iconic Chicago skating destination where you can skate to cheerful holiday music and watch your reflection in the Bean.

Try skating at Navy Pier’s Winter Wonderfest with a rink brought to you by the Chicago Blackhawks and also be surrounded by many other fun winter activities. 

The Maggie Daley Skating Ribbon is a particularly fun outdoor skating rink as this circularly shaped rink allows your to race your friends.


Here are the Christmas Shows in Chicago You Need to See

There’s nothing better than walking into a warm theater on a cold night and seeing a Christmas show. Chicago has a wide range of shows throughout the holiday season and they’re guaranteed to keep your Christmas spirit alive.

The renowned Joffrey Ballet is performing the Christmas classic The Nutcracker at the Auditorium Theatre from December 1- 30th. The Auditorium Theatre, a national landmark, is one of the best theaters in the city with its central location and great nearby dining options.

For a family-centered show, check out ‘Twas the Night Before Christmas at the Emerald City Theatre. Don’t forget to stop by the post-show hot chocolate bar with sweet and savory pastries and meet the cast.

Don’t miss the classic Dickens story A Christmas Carol brought to life on stage at the Goodman Theater.


Take the Family Sledding in Chicago at These Spots

Photo courtesy of Chicago Park District

Button up, it’s officially sledding season. Finding the perfect hill to sled down is a major priority during the winter holiday season. Chicago has a wide array of sledding sports ranging from novice to daredevil.

The northwest Caldwell Woods may no longer have the famous toboggan slides, but it does still have one of the cities best sledding areas with lights at night, easy parking, and indoor bathrooms.

Montgomery Ward Park is a great option for kid-friendly sledding near the river with the nearby Peet’s Coffee and Tea for a warm beverage after taking on the sled.

Lincoln Park is a great neighborhood with lots of family-friendly sledding opportunities in addition to great places to stay cozy with a warm drink or fireplace.  

For the real family daredevil, head to the Soldier Field Sled Hill and take on the 220-foot slope that’s thought of as one of Chicago’s best sledding spots. Don’t worry if there’s not a heavy snowfall the night before, they’ll make artificial snow for the slope if there isn’t enough natural snow.


The Best Holiday Concerts in Chicago

Chicago’s schedule is full throughout November and December with many different kinds of holiday concerts for concert-goers of all ages.

The Trans Siberian Orchestra is here on December 28th and is a guaranteed good time for a holiday celebration or check out a concert for the kids at one of the many Chicago Symphony Orchestra holiday-themed shows.

For a more pop-centered holiday celebration try the B96 Pepsi Jingle Bash, which is held annually at Allstate Arena and features some of the most popular current artists.

Other local Chicago radio stations also host holiday concerts with a wide assortment of genres according to their station such as the pop station 103.5 KISS FM Jingle Ball and the alternative rock-themed 101WKQX The Night We Stole Christmas.

Another way to celebrate the songs of Christmas is to watch the caroling at the Bean and become a part of the action by joining the caroling every Friday through late November and December.


Celebrate New Year’s Eve in Downtown Chicago

Photo courtesy of Telemundo Chicago

As we shift into the new year, focus on making this New Year’s Eve the best one yet… Chicago is a major destination for New Year’s Eve and depending on your interests, there many different events for you to enjoy as we transition into a new year.

The range of celebrations feature concerts, parties, speakeasy cruises, and galas. The options for how to ring in the new year are endless and we’re here to help by showing the best ways to celebrate New Year’s Eve.

Unfortunately, the Chicago star will not be rising this year, but check out a great holiday party to watch the NYC ball drop and enjoy your first moments of 2018. Different party options include Big Night Chicago, Brew Year’s Eve, Chicago Resolution Gala at Navy Pier, and Rock Around the Clock. With so many great options, New Year’s Eve in downtown Chicago is guaranteed to be a great time.

If you’re in the market for a new Chicago apartment or condo and want to fully experience our city’s winter celebrations, click the link below!


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