Each year, some 30 million people visit Chicago, and for good reason.
For years the city has consistently been voted one of the best in the U.S., and for a country this size that is no small feat.
With its iconic Chicago River, well-known architecture, and Lake Michigan beaches, it is truly the gem of the Midwest.
But winter is when the Windy City really shines.
The lights and storefronts combined with cool, crisp air are sure to bring anyone back to their childhood holidays.
Unsure where to start?
Look no further.
Here are some of the must-do winter activities in Chicago.
Hey! Looking for more fun Illinois guides? Check these out!
- Illinois National Parks: Insider Tips for 5 Iconic Sites
- 51 Fun Facts about Illinois (that most people don’t know!)
- 15+ Songs about Illinois to Brighten Your Day
Getting around Chicago
Don’t forget that it’s much easier to see Chicago by car so you can get around on your own.
Rental cars are perfect if you’re flying into the state.
We recommend using Discover Cars price comparison to find the cheapest deals!
Holiday Themed Tours in Chicago
If you’d prefer to have someone else show you around, check out these festive Chicago tours that you could go on, or continue reading our guide that you can follow yourself!
- Chicago Holiday Lights Segway Tour – Enjoy this 2-hour intimate night tour as you explore the twinkling lights around the city. You’ll stop by Christkindlmarket, Michigan Avenue, and more!
- Holiday Hike Chicago-Style: Festive Food & Walking tour – How does deep dish pizza, chocolate, hot dogs, and seasonal craft beer sound? Explore the sights and sample some of the best festive food Chicago has to offer on this walking tour!
- Train & Walking Tour: Chicago Passageways – Pedway & Holiday Sights – Take a tour of Chicago’s Pedway system—a network of underground tunnels that allow pedestrians to pass from one end of the Loop to the other—and enjoy seasonal holiday sights and sounds along the way!
The weekend before Thanksgiving kicks off the holiday festivities in Chicago, and there is no more momentous occasion to set the tone than the Lights Festival.
It all starts Friday night in the Wrigley Building Centennial Plaza with a much-anticipated tree lighting ceremony.
When the lights come on, the holiday season has officially begun.
The following morning, bring the whole family down to Lights Festival Lane (401 North Michigan Avenue) where there will be music, food, family-friendly booths, and you can even get your picture with Santa!
Next, watch the kids’ eyes fill with awe as Mickey and Minnie Mouse act as Grand Marshals in a parade that lights up more than 200 trees along the way.
Don’t be in a hurry to leave at the conclusion of the parade.
The city has one more surprise in the form of fireworks.
For over a century, the “official” Chicago Christmas Tree has illumined the city and delighted onlookers from all over the country.
A true piece of Chicago history, the tradition lives on in Millennium Park.
Be sure to get your spot early to enjoy live music including Broadway performances as the sun goes down.
Next, it’s the main event, the tree lighting!
This four-story behemoth will amaze, and a fireworks show rounds out the night.
Located in the Chicago Loop, this event takes place near the famous Cloud Gate mirrored sculpture, known affectionately to the locals as “The Bean”.
This event is for the whole family.
Bring the kids for a night they’ll never forget.
Right next door to Millennium Park is the Maggie Daley section of Grant Park where a seasonal ice-skating ribbon is one of the best winter things to do in Chicago.
Open annually since 2014, the ribbon provides a means for visitors to get some fresh air and get their muscles moving in the cold.
Don your skates and immerse yourself in the heart of the city surrounded by beautiful architecture. Skates and lockers are available to rent for a small fee.
From mid-November through the New Year, the Zoolights event transforms the 49-acre Lincoln Park Zoo into a veritable winter wonderland that’s perfect for little ones.
More than 2 million twinkling LED lights bring holiday cheer to the pathways and structures.
While the animal houses are closed at this time you may get lucky and see them in their outdoor habitats.
The zoo is normally free but there is a small $5 fee for general admission tickets that goes toward conservation efforts. However, check their website prior to visiting for information on snagging free admission on Mondays.
Not to be outdone, for over four decades Brookfield Zoo has drawn crowds to their Holiday Magic nights.
Your whole family will be dazzled by the millions of lights covering the landscape.
Wander under a 600-foot light tunnel and help the kids find hidden gnomes around the park.
Be sure to bring their letters for Santa.
There’s a special drop-off location right at the zoo! Shopping is also available as well as food and beverages.
And if you’re feeling up for a challenge, why not get the family together for a run?
The Reindeer Run is a fun run that covers two miles, all within the zoo among the lights.
Can’t get enough of the lights?
The Chicago Botanic Garden offers a light experience unlike any other.
Appropriate for children, but exhilarating even for adults, you will not soon forget the display here.
Groups are staggered in 15-minute increments in order to ensure that everyone is able to fully appreciate their surroundings.
Stroll through the Winter Cathedral, a 100-foot archway of lights, gaze at the fire garden featuring hundreds of burning torches, and watch as light shows dance across your path.
This event sells out fast, so get your tickets early!
Every winter, the Morton Arboretum becomes aglow with their Illumination series just 25 miles to the west of the city.
Stroll a one-mile path surrounded by trees of bright colors and interactive displays, all while listening to festive seasonal music.
Get a s’mores kit and have a yummy treat by the fire.
For the 18 and over crowd, check out Electric Illumination.
Trance and Progressive House music sync up with the light displays for a one-of-a-kind experience.
And don’t miss the laser light show at the end.
If you’re looking for an adults-only night, IllumiBrew is for you.
Beers, ciders and meads from local Chicago breweries will be available to taste test.
The building that houses the Museum of Science and Industry is a Chicago icon as it is the only one remaining of those built for the 1893 World’s Fair.
A great way to spend a day any time of year, the sprawling museum features everything from a German submarine to a five-story movie theater.
And every winter it showcases two very special exhibits, Christmas Around the World and Holidays of Light.
Wander through the more than 50 trees on display, each decorated to represent a different culture, and learn about the various cultures for whom light is at the forefront of their holiday celebrations.
Macy’s Department Store on State Street is a staple during the holidays in Chicago.
Adorned inside and out with colorful, vintage embellishments to delight your inner child, it epitomizes Chicago in winter.
Lively scenes and animated characters tell a story in the outer windows, one that includes The Joffrey Nutcracker Ballet.
You may even see some Chicago landmarks in the scenes.
Take the kids to see Santa Claus at the Cozy Cloud Cottage, go Black Friday shopping and get some of the best deals.
Plan in advance to reserve a table in the Walnut Room where you and your loved ones can have a meal while you bask in the glow of a two-story Christmas tree in the center of the room.
10. Navy Pier
Hugging the Lake Michigan shoreline, Navy Pier is a place for families to play.
There’s a Children’s Museum, shops, restaurants, and rides.
And who could miss the Centennial Wheel along the skyline with its closed, comfortable seating and unparalleled views of the city?
But wintertime is when the pier really shines.
With lights, Christmas trees, and ornaments galore, the Winter Wonderfest really lives up to its name.
Hitch a ride on the train or the carousel.
Enjoy a number of carnival rides.
Let the kids be the drivers on the bumper cars, the one place where crashing is not only okay but encouraged.
This is definitely an adventure you won’t want to miss.
11. Pop-Up Bars
Pop-up bars are the newest annual attraction for city-goers.
As the weather grows colder, many of the local watering holes shed their usual appearance and transform into holiday hotspots with fun and elaborate themes.
Belly up to the bar with your friends and enjoy festive adult beverages and immersive rooms designed to put you in a merry mood.
With plenty of photo ops, the memories and laughs will last a lifetime.
In a city the size of Chicago, talented musicians abound, and Candlelight Concerts are a unique way to enjoy the sounds of the season.
The concerts take place in beautiful venues all over the city and feature all different styles of music such as classical, jazz, soul, and rock.
The one commonality is the ambience.
Hundreds of candles cast a warm glow on the stage, giving concertgoers a sense of serenity and peace. Relax and enjoy the gift of music with the ones you love.
Guests must be 8 years or older to attend these events.
One of the best things to do in Chicago in winter is visit the theatre for the Nutcracker.
But this Nutcracker is unlike any you’ve seen thanks to Joffrey Ballet.
Join Marie on a magical adventure through the 1983 Chicago World’s Fair.
With whimsy and grace, the dancers will command your attention.
You’ll be entranced by the intricate sets, the colors, the sounds.
As if the performance wasn’t enough on its own, the bonus is that you will find yourself learning some of the rich history of Chicago to boot.
The Goodman Theatre is the home of this classic tale of greed and redemption in Chicago.
Located in the Chicago Loop and walking distance to many of the other places featured, the Goodman has been part of the Chicago landscape for over 80 years and A Christmas Carol has graced the stage for over four decades.
Take your seat and enjoy the story of Ebenezer Scrooge and his nightly visits from the Ghosts of Christmas Past, Present, and Future played by a cast of talented local actors on a renowned stage!
When in Chicago, why not take in a game?
Two major professional sports teams play in The United Center, The Chicago Bulls and the Chicago Blackhawks.
The Chicago Blackhawks have been entertaining fans since 1926.
In that time, they have been the winners of the Stanley Cup six times over and have called The United Center home since 1995.
Founded in 1966, the Chicago Bulls have garnered the attention of fans worldwide with the likes of Michael Jordan and Scottie Pippen bringing them six NBA Championship wins.
Grab a Chicago style hot dog, have find your very comfortable seat, and be a part of the action.
Maybe you’ll even end up on the jumbotron!
Since 1992, in a grand gesture to spread holiday cheer, the Chicago Transit Authority treats its commuters to their very special Holiday Train.
Inside and out, every inch is covered in lights, decorations, ornaments, and pictures made by local school children.
Even the seats are lined with Christmas fabric.
But the most exciting part is the flat car that pulls Santa and his reindeer through the Chicago Loop.
Hop aboard and join Santa on his route or watch with delight as the train makes its way around the city.
Either way, this train is sure to make you smile.
Last on the list, but most certainly not least is perhaps the best of the best things to do in Chicago during winter.
A longstanding tradition, the Christkindlmarket harkens back to the 16th century when the first open air Christmas market came on the scene in Nuremberg, Germany.
Chicago’s version ushers in visitors from far and wide who enjoy the warm, nostalgic feel it gives them.
Stroll through the stands and find the perfect gift for everyone on your list.
Have a German pretzel, sip some Belgian hot chocolate, and take home some handcrafted decorations to put on the tree.
The Christkindlmarket takes root in Daley Plaza, with sister sites in Aurora and Wrigleyville.
But really, this market will transport you to another time, all while tucked away in the one-and-only city of Chicago.
Pin for Later!
Get the All-American Travel Secrets!
Don't miss out on America's hidden gems!