Falling Into Winter


Fall & Winter Happenings in Chicago

By Dave Lifton

Chicago Marathon 

October 8

The Chicago Marathon brings elite distance runners from around the world to the Windy City. Cheer the athletes at the finish line in Grant Park or anywhere else along the 26-mile route. 

Arts in the Dark 

October 21 

This nighttime parade brings cultural institutions and artists from all over Chicago in creative and colorful costumes to State Street to celebrate the power of art. 

Nightmare on Clark St.

Until October 31

The Bamboo Club in Wrigleyville transforms into a multi-level haunted house. The pop-up experience is for those aged 15 and over, and people under 18 must be accompanied by an adult.

Pumpkin Patches

Until October 31

Within a 90-minute drive of Chicago are many apple orchards and pumpkin patches. You can enjoy family-friendly activities like corn mazes, petting zoos and hayrides. 

Scary Movies

Until October 31

Horror film enthusiasts will find their way to the Music Box Theatre in Lakeview and the Logan Theatre in Logan Square, where they’ll have the opportunity to enjoy nightly screenings of timeless classics from the genre.

Día de los Muertos 

Until December 10

Pilsen’s National Museum of Mexican Art’s 35th annual Día de los Muertos exhibit honors and celebrates the lives of lost loved ones through this time-honored tradition. 

13th Floor Haunted House & Old Joliet Haunted Prison 

Until November 5

In Schiller Park, near O’Hare International Airport, 13th Floor Haunted House returns for its 10th year with a pair of post-apocalyptic scary experiences. In suburban Joliet, the former Joliet Correctional Center is transformed into a haunted prison with two prison-themed experiences, plus zombie laser tag and two bars. 


November 10 – January 7, 2024

In suburban Glencoe, this annual light fest turns the Chicago Botanic Garden into stunning installations of color, light and music created by artists from across the globe.  

Christmas Around the World 

Mid-November – January 7, 2024

One of the Museum of Science & Industry’s most popular exhibits fills the Rotunda with more than 50 trees in displays that portray international holiday traditions. 

Ice Skating

Mid-November – Spring 2024

Ice skating lovers have two outdoor options in the heart of Chicago. The McCormick Tribune ice rink is located underneath “The Bean” in Millennium Park, and Maggie Daley Park’s skating ribbon is a quarter-mile track with curves, inclines and declines. Skates and lockers are available for rental at both facilities. 

Chicago Christmas Tree 

November 17

Chicago’s official Christmas tree will be lit by Mayor Brandon Johnson during a ceremony at the Washington St. entrance to Millennium Park. 


November 17 – December 24

One of Chicago’s favorite winter traditions returns to Daley Plaza. The outdoor market replicates those found in Germany and features holiday gifts from around the world, German food and beverages and plenty of holiday cheer. 


November 17 – January 7, 2024

The Lincoln Park Zoo gets festive for the holidays. Stroll the grounds and see colorful displays that contain more than 2.5 million lights.  

Magnificent Mile Lights Festival

November 18

The 32nd annual festival kicks off the holiday season with a day’s worth of activities, concluding with a parade down Michigan Avenue, with 1 million lights in the trees being turned on. Mickey and Minnie Mouse are this year’s Grand Marshals. 


November 18 – January 6, 2024

The trees of Lisle’s Morton Arboretum serve as canvasses for immersive light displays and along the one-mile path are concession tents with hot beverages and s’mores kits. 

Winterland at Gallagher Way

November 21 – December 31

This annual event brings Christmas cheer to Wrigley Field, with a Christkindlmarket outside the historic stadium and a skating rink and many other fun activities taking place inside the “friendly confines.” 

Chicago Thanksgiving Parade

November 23 

With loads of balloons, floats, dancers and marching bands, the parade heads up State St. in the Loop to the delight of children of all ages.

Holiday Magic at the Brookfield Zoo

November 24 – December 31

The main attraction at is the displays featuring more than 2 million lights. But there are other festivities, such as ice carvings, carolers and pictures with Santa Claus. 

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