Planning to visit Chicago in the winter? Here is a guide to great winter activities and holiday-themed events in Chicago along with where to stay and what to eat. For more indoor things to do in Chicago, check out our post on 39 Best Things to do in Chicago. 

The first time I stepped foot in Chicago? On Christmas Day more than a decade ago! The city looked gorgeous. The holiday lights sparkled brilliantly everywhere and downtown was a dream – draped in twinkling lights and ribbons. So festive. Chicago in winter looks almost ethereal.

The city also packs a punch of holiday-themed activities plus has many indoor attractions. Also, flights to Chicago are often cheap in the winter making Chicago a great winter holiday destination or even better, the perfect place to head to if you want a White Christmas. 

Chicago Navy Pier decorated for the holidays

Tips for visiting Chi-town in the winter

Visiting Chicago in winter is way different than visiting Chicago in summer. It gets really cold and windy – more than you would imagine. Also, the weather almost always feels at least five degrees colder than what is predicted. You have to dress appropriately or you’ll freeze your socks off. 

Walking time between attractions almost doubles as visitors struggle to keep up with the dry, chilly air. We recommend taking the L (loop transport) to major attractions or flagging down a cab or Uber. Fortunately, Chicago has plenty of transport options and you won’t be left standing out in the snow for long. 

You need to plan every day such that there’s a great mix of outdoors and warm indoors attractions. If you plan to visit many museums or ticketed attractions Chicago attractions pass might come in handy. 

Book your accommodations in advance as winter is a popular time to visit during the holidays and weekends. Stay in the Loop or city center to remain close to major holiday attractions. 

Dress for comfort and warmth and you can even enjoy a lakeside stroll and take in the skyline views even in the winter. 

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Views from Millenium Park

Best Things to do in Chicago in the winter

Here are our favorite things to do in Chicago in the winter. In this holiday-themed article, we mostly cover just cold weather attractions. For a look at Chicago’s famous year-round tourist attractions check out our post on Best Things to do in Chicago for first-time visitors

Ice Skate at Millennium Park

In winter, the free area under the Bean is transformed into the McCormick. Tribune Rink. Locals, as well as visitors, love to ice skate at the rink while listening to holiday music. While ice skating you also have gorgeous views of the city and can wrap it up with a cup of warm coffee from Starbucks just opposite to Millennium Park. The rink also has skate rentals in case you don’t own a pair. 

While in Millennium Park, don’t forget to see it’s many attractions including the famous Bean, Jay Pritzker Pavilion, Lurie Garden, etc. The Bean looks fabulous when partly covered by snow and creates some stunning photo opportunities. Also, just across the Millennium Park is the free Chicago Cultural Center which has beautiful Tiffany glass domes and is a great place to spend time indoors.

The Bean looks beautiful when covered in snow

See the Magnificent Mile Lights

While the Magnificent Mile is a great place year-round, it is even more vibrant during the Holidays when the trees are studded with Holiday Lights. The Magnificent Mile Holiday Lights Festival starts in November and the trees stay lit up well into January.

The event kicks off with a grand Tree Lighting parade down Michigan Avenue. The parade has marching bands, helium balloons, and it is a lot of fun. Musical performances, family events, and winter wonderland activities are held on weekends throughout the holiday months. To check out this year’s festivities, read more here

Walk along the Lakefront Trail

While you won’t think of this as a winter activity, we would suggest bundling up and walking along the Lakefront Trail in winter to experience the crazy weather from a different angle. You will get to see spectacular ice formations along the frozen Lake Michigan.

Here’s a fun fact: the lake is so large that it never freezes completely. That’s why you should never tread on the ice, you don’t know when it will give way.

On the Lakefront Trail, you will also see locals going about their daily runs and jogs – some even dressed in shorts or running bare-chested in the freezing weather! 

Views of the skyline from Museum Campus

Visit the Christmas market

Christkindlmarket in Chicago is inspired by the famous German Christmas Market in Nuremberg. The market usually sets up around Thanksgiving and lasts up to Christmas Eve. There are many vendors selling Christmas gifts, holiday beverages, foods, and more at the holiday market.

You can pick up one of a kind, often handmade items such as eclectic Christmas ornaments, wooden toys, cuckoo clocks, jewelry, and clothes, as well as really cool Christmas gifts. Vendors also sell German sweet and savory delicacies as well as Gluhwein, the famous spiced holiday wine. 

If you are spending a long weekend in Chicago, then read this 3-day Chi-town itinerary now!

Enjoy the holiday window decor

While not as iconic as New York, Chicago also has its own trendy holiday decor in-store display windows. The best places to see the holiday displays are along Michigan Avenue and State Street. Macy’s on State Street especially puts on quite a spectacular holiday display.

We also love the holiday decor inside Water Tower Place. With many signature brands present at both locations, this is also a great time to shop for Christmas gifts. 

Macy’s holiday display

Attend the tree lighting ceremony

The City of Chicago Christmas tree lighting is one of the most popular holiday events in Chicago. The event features musical performances by celebrities and appearances by Santa Claus and Mrs. Claus. The event takes place in Millennium Park.

An art market in Millennium Park also usually accompanies the event. Attending the tree lighting ceremony is a fun, cheerful holiday event and an absolute must if you are in Chicago on the day of the event. 

See the Thanksgiving parade

The annual Chicago Thanksgiving parade is held on State Street. This much-anticipated event has over 100 units of helium-filled balloons, floats, marching bands, performers, equestrian units, and more. Read more details about this year’s parade including when it is held here.

The parade is known as Chicago’s Grand Holiday Tradition and has been held since 1934. The parade is also nationally broadcast, which means you can catch it even if you are not in Chicago. 

See holiday decor everywhere

Have fun at the Lincoln Park Zoo Lights Festival

We love visiting the Lincoln Park Zoo year-round. After all, it is free and has a great variety of animals. However, the zoo turns spectacular in the holiday season when over a million lights are used to decorate trees and almost everything in the park. The event also includes many other festive activities including taking pictures with Santa Claus, lighted 3d displays, holiday snacks, and drinks, etc. This is also a great time to see animals at night. 

See trees from Around the World at the Museum of Science and Industry

Christmas Around the World exhibit at the Museum of Science and Industry explores holiday traditions in different countries. This is one of the most underrated holiday events in Chicago.

You can see over 50 Christmas trees decorated in keeping with the culture and tradition of their home country. We love the sparkling trees – they are also perfect for all your holiday social media pics!

The event is included in regular entry tickets, so you can also see many interesting science and technology exhibits at the same time. This visit is definitely a hit with the kids and a must if you are visiting Chicago in winter with the family. 

Chicago looks gorgeous even in winter

Have fun at the Skating Ribbon

The Skating Ribbon in Maggie Daley Park in downtown Chicago is one of the best attractions for families. Maggie Daley Park is located right behind Millennium Park but is rarely visited by tourists. The park has lots of things to do for kids.

The most popular attraction is the Skating Ribbon that winds up throughout the park. Skate rentals and hot chocolate are available at the park to complete your experience. The park also has play areas and picnic tables to enjoy the sunshine in the winter. 

Attend a Chicago Bulls game 

Chicago loves it’s sports teams and there are plenty of games to watch even during winter. You can watch the Chicago Bears play football at Soldier Field from September till December or the Chicago Bulls play basketball at United Center throughout winter. For ice hockey, watch out for the Chicago Blackhawks and Chicago Wolves. 

Soldier Field, Chicago

See a holiday musical in Theater district

Chicago’s Theater District has many holiday shows and operas and is a great place to watch a musical. We especially love watching holiday shows as you can skip the cold weather and feel cozy indoors while still enjoying the festive atmosphere.

The Theater District features the most popular holiday shows during the season including classics like A Christmas Carol at the Goodman Theatre, It’s a Wonderful Life by the American Blues Theater, and the Nutcracker at Chopin Theater. 

Enjoy the Black Friday shopping

Chicago Premium Outlets in Aurora is a great place to line up at midnight and enjoy shopping for Black Friday holiday deals and discounts. Other favorite outlet shopping places are Gurnee Mills Outlet Mall – they even have a Rainforest Cafe, Fashion Outlets of Chicago, etc.

If you don’t want to leave the city, but still get shopping done then try the Maxwell in South Loop. For best window shopping opportunities, try Magnificent Mile and Water Tower Place. We love visiting the Water Tower Place with our kids as it has the American Girl store as well as the Lego store. 

Fireworks display at Navy Pier

New Year’s fireworks at Navy Pier

The Navy Pier has many holiday happenings throughout the winter including tree lighting, Santa Claus appearances, caroling, etc. Their Winter Wonderfest event has indoor ice skating, carousel, and more.

We also love their free fireworks displays and feel this is the best way to ring in the New Year in Chicago. We recommend dressing warmly in layers for the fireworks as it gets super cold out on the lakefront at midnight. 

While you are at Navy Pier, enjoy the other attractions including the Centennial Wheel, other fun rides, children’s museum, the food court, etc. Oh and don’t forget to eat the famous Garrett Popcorn and the deep dish pizza at Giordano’s – both have a convenient location at Navy Pier. 

Navy Pier in the holiday season

Have a romantic dinner with your sweetheart

If you are celebrating Valentine’s Day in Chicago, then many restaurants have a fixed four-course meal to enjoy the day with your sweetheart. Or you can attend a romantic dinner cruise on Lake Michigan followed by music and lots of quality time. Or you can enjoy the views from the Signature Lounge in the John Hancock tower. Chicago has quite a few romantic things going on for Valentine’s Day.

Attend St. Patrick’s Day Celebrations

Okay, so St. Patrick’s Day doesn’t technically come in the winter. The day is celebrated on 17th March every year but if you know Chicago, it’s still as cold as it’s in winter! Chicago has one of the best St. Patrick’s Day Celebrations in the world.

The highlight is the Chicago River Dyeing Ceremony where the entire river turns green. Following the ceremony, parades are held everywhere in the city and then it’s time for a green beer bar crawl. To plan a St. Patrick’s Day trip to Chicago, read our post now. 

Chicago on St. Patrick’s Day

Besides these, Chicago has many other Christmas themed events and holiday festivities going on in winter including pop up bars, shopping deals, bakeries selling holiday treats, themed meals, etc. Many of these events continue well beyond Christmas and ensure that you have a great time in Chicago irrespective of when you visit. 

We hope you liked our guide on the best things to do in Chicago in the winter. Did we miss any top attractions? Let us know in the comments.

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