From crisp fall days with gem-toned leaves to twinkling holiday lights turning the city into a wondrous snow globe scene, Chicago is glorious this time of year. For things to do in Chicago over winter, read on! Annual seasonal traditions, outdoor ice skating, winter tours and more make it a perfect destination for all ages.

Here are the absolute winter musts in Chicago: 

Lace up Some Skates

Ice Skating during a Snowfall

On shimmering winter days, Chicagoans love gliding around one of the city's many outdoor ice rinks. Whether it's the outdoor rink at Millennium Park (pictured above), the skating ribbon at Maggie Daley Park, neighborhood rinks sponsored by the Chicago Park District, the rink outside the big red barn at Lincoln Park Zoo or the winter wonderland known as the rooftop Sky Rink at The Peninsula Hotel, there's a skating experience to suit every taste.

Grab Some Gifts

Macy's exterior holiday decor in Chicago

Chicago is a shoppers' paradise. In fact, the city has been named the No. 2 shopping destination in the country by Travel + Leisure. Stroll high-end boutiques and mega shopping malls along The Magnificent Mile. Admire the extravagant holiday window displays in the Loop at Macy's on State Street.

Or head to neighborhoods like Lincoln SquareAndersonville, the Southport Corridor in Lakeview or Wicker Park/Bucktown to find something for everyone on your holiday gift list.

Explore with the Kids


The city is packed with family-friendly fall and winter activities. Don a free pair of 3-D glasses to fully experience ZooLights (pictured above) at Lincoln Park Zoo.

Head to Navy Pier for Winter WonderFest, a massive indoor amusement park of bouncy houses, climbing structures, and even a skating rink.

Hit the local favorites


Stroll the authentic German Christkindlmarket (pictured above) at Daley Plaza to buy beautiful glass ornaments and sip cocoa or mulled wine.

Gaze at the sparkling Millennium Park Christmas Tree or the over-the-top tree that nearly touches the Walnut Room ceiling at Macy's on State Street (say hi to Santa while you're there).

Watch the Art Institute of Chicago lions get their traditional evergreen wreaths at the annual ceremony. Or warm up those vocal chords with Caroling at Cloud Gate (aka "The Bean") in Millennium Park.

In Chicago's neighborhoods, attend a sing-a-long at the Music Box Theatre on Southport Avenue or admire the St. Lucia Festival of Lights in Andersonville.

Seasonal Traditions

Diners in a Chicago restaurant during Restaurant Week

Make your reservations for Chicago Restaurant Week (Jan. 25-Feb. 7, 2019, pictured above) to indulge in special prix fixe menus around the city. Or, celebrate the city's world-class theater scene with discounted Chicago Theatre Week (Feb. 7-17, 2019) tickets.

Experience the splendor of Chinese New Year (Feb. 16-March 4, 2019) celebrations throughout Chicago with vibrant parades, cultural performances and authentic food. 

Winter Cravings


For soul-warming meals, grab a table at Big Jones (Southern favorites) in Andersonville, Sapori Trattoria (Italian) in Lincoln Park or Honey Butter Fried Chicken (comfort food) in Avondale.

For over-the-top hot chocolate, swing by Mindy's Hot Chocolate, a go-to dessert spot, or BomboBar, a walk-up window in the West Loop neighborhood. 

Festive Shows

Joffrey Ballet The Nutcracker performer on stage in Chicago

Theatergoers make annual pilgrimages to shows like Joffrey Ballet's The Nutcracker (pictured above), Goodman Theatre's A Christmas Carol and T'was the Night Before Christmas at Broadway Playhouse.

Stroll Our Museums

AIC Wreathing Lions

Experience Christmas Around the World and Holidays of Light at the Museum of Science and Industry, with some 50 trees decorated to represent different countries and holiday traditions. At the Art Institute's Thorne Miniature Rooms, select rooms have been decked out in tiny festive decorations.

Take in the Freedom, Resistance and The Journey Toward Equality exhibit at The DuSable Museum of African American History. Or revel in the winter night sky with a show at the Adler Planetarium.

Embark on a Winter Tour

Millennium Park Christmas Tree

What better way to see Chicago's magical holiday lights than by a guided tour? Hop aboard Chicago Trolley and Double Decker Co. for a tour of lights along The Magnificent Mile, as well as Daley Plaza, John Hancock, Macy's and more. Jump on a Segway for Absolutely Chicago Segway's festive Holiday Lights Tour.

Or see the lights from thousands of feet in the air. Take a holiday light helicopter tour with Chicago Helicopter Experience or Vertiport Chicago. Even public transit gets into the spirit with its annual CTA Holiday Train, featuring decorated train cars, holiday music, and lights as well as Santa himself as the conductor.

Find more things to do and Chicago itinerary ideas for your visit, or pick a neighborhood and start exploring.

Related Listings

Absolutely Chicago Segway Tours
238 E. Monroe
Chicago, IL 60603
(312) 552-5100

Millennium Park
201 E. Randolph St.
Chicago, IL 60601
(312) 744-6050

The Joffrey Ballet
Joffrey Tower, 10 E. Randolph St.
Chicago, IL 60601
(312) 739-0120

Adler Planetarium
1300 S. Lake Shore Dr.
Chicago, IL 60605
(312) 922-7827

DuSable Museum of African American History
740 E. 56th Pl.
Chicago, IL 60637
(773) 947-0600

Lincoln Park Zoo
Cannon Dr. at Fullerton Parkway
Chicago, IL 60614
(312) 742-2000

The Walnut Room
111 N. State St., Seventh Fl.
Chicago, IL 60602
(312) 781-3139

Goodman Theatre
170 N. Dearborn St.
Chicago, IL 60601
(312) 443-3800

Sapori Trattoria
2701 N. Halsted St.
Chicago, IL 60614
(773) 832-9999

Christkindlmarket Chicago
50 W. Washington St.
Chicago, IL 60602
(312) 494-2175

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Navy Pier
600 E. Grand Ave.
Chicago, IL 60611
(312) 595-5300

Macy's on State Street
111 N. State St.
Chicago, IL 60602
(312) 781-1000

The Magnificent Mile® Association
625 N. Michigan Ave., Ste. 401
Chicago, IL 60611
(312) 642-3570

Art Institute of Chicago
111 S. Michigan Ave.
Chicago, IL 60603
(312) 443-3600

Museum of Science and Industry
57th Street and Lake Shore Dr.
Chicago, IL 60637
(773) 684-1414

Chicago Trolley and Double Decker Co.
Water Tower Pumping Station
Chicago, IL 60611
(773) 648-5000

The Peninsula Chicago
108 E. Superior St.
Chicago, IL 60611
(312) 337-2888

Chicago Helicopter Experience
2420 S. Halsted St.
Chicago, IL 60608
(855) 414-8687

Big Jones
5347 N. Clark St.
Chicago, IL 60640
(773) 275-5725

Theater Wit
1229 W. Belmont Ave.
Chicago, IL 60657
(773) 975-8150

Maggie Daley Park
337 E. Randolph St.
Chicago, IL 60601
(312) 742-3918

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