Celebrate Halloween happenings and festive winter traditions in Chicago.

Whether you’re planning to visit Chicago with your group in fall or winter, you’ll find fun seasonal celebrations happening throughout the city. Autumn is all about Halloween and spooky spectacles, from a fantastical evening parade to ghost tours. While winter brings sparkly holiday fun like Christmas caroling in snowy Millennium Park and wandering through a dazzling lights display at Lincoln Park Zoo. Here are 11 fun Chicago holiday ideas for groups to get your planning started.


With events ranging from a nighttime arts parade to an authentic Day of the Dead celebration, autumn is an awesome time to visit Chicago with your group.


Arts in the Dark Jester costume

Harnessing the imagination of Chicago's creative community, renowned institutions that include the Art Institute of Chicago and Lookingglass Theatre Company combine forces to produce a magical evening Halloween parade in downtown Chicago on October 20, 2018 from 6-8pm. Marvel at the large-scale puppets, costumed performers, elaborate floats and art-filled performances as the procession moves north along Columbus Drive from Balbo to Monroe Street in spectacular fashion. 


Day of the Dead

Experience an authentic Day of the Dead celebration at the National Museum of Mexican Art in Pilsen on October 28, 2018 from 3-8pm. The museum and nearby Harrison Park will converge to create a homage to dearly departed loved ones. Traditional make-your-own ofrendas (altars), live music, face painting and art activities transform the park’s soccer field into a festive community gathering place similar to one you would find in Mexico on Día de los Muertos. Also check out the museum's Día de Muertos: A Spiritual Legacy exhibit, on view through December 9, 2018, which features traditional and contemporary artworks that honor the Day of the Dead.


Nightly Spirits’ two-hour Chicago Ghost Tour appropriately begins at the The Red Lion Pub in Lincoln Park, reputedly one of the city’s most haunted bars. A guide takes ghost hunters through dark alleyways and around creepy buildings as they tell tales of murdered Prohibition-era gangsters and ghosts that refuse to leave their dwellings. The approximately one-mile tour includes stops at two or three bars to sample spirits of a different kind. The purchase of drinks is not included or required. Customized private group tours are available.


Uncle Dan's Thanksgiving Parade

Thanksgiving day begins bright and early with this cheery morning parade that takes place on November 22, 2018, along historic State Street from 8-11am. Join the crowd in cheering as a lively procession of huge helium balloon characters, colorful floats and marching bands make their way through the Loop.


Winter is a magical time of year to visit Chicago, with beloved seasonal traditions that include the festive Christkindlmarket and a spectacular holiday lights show at Lincoln Park Zoo.


Christkindlmarket Shopping

Stroll through a holiday village inspired by Germany’s Nuremberg Christmas market at Christkindlmarket Chicago in downtown Daley Plaza from November 16-December 24, 2018. Rows of quaint wooden stalls decked with twinkling lights and garland sell handcrafted holiday gifts like glass ornaments and old-fashioned toys. Enjoy warm spiced wine, gingerbread and other traditional treats. 


MSI Christmas Around the World

A holiday tradition since 1942, the Museum of Science and Industry celebrates its annual Christmas Around the World and Holidays of Light from November 15, 2018 through January 6, 2019. You’ll be awed by the sparkling four-story Grand Tree surrounded by a forest of more than 50 trees and displays representing the holiday traditions of cultures around the globe. On the weekends catch international music and dance performances, along with build-an-ornament workshops and photos with Santa. Make an advance group reservation for 15 or more to visit the museum and receive a discount on admission.


Copy of Caroling at Cloud Gate

From mid-November through December, sing holiday favorites with local Chicago choral groups during Caroling at Cloud Gate on Friday evenings in Millennium Park with the beloved “Bean” sculpture as a picturesque backdrop. Afterwards, glide around the spacious outdoor McCormick Tribune Ice Rink, a Chicago winter tradition for more than 15 years. Skating is free and open to the public through early March (weather permitting), with skate rentals available for a fee. Or whoosh along the winding Skating Ribbon at next-door Maggie Daley Park, where you can ice skate with Santa and catch carolers serenading the crowds on special days. 


Lincoln Park Zoo ZooLights

Ooh and aah at the dazzling animated light displays during the free ZooLights at Lincoln Park Zoo from November 23, 2018 through January 6, 2019, where you’ll also find fun crafts for kids, frosty beers for the grown-ups, live ice sculpture carving and visits with Santa Claus. More than two million lights transform the Lincoln Park Zoo into a glittering winter wonderland. Look for special ticketed events on select dates, such as the November Holiday Market.


Beginning in late November, hop aboard a festively decorated trolley and join the Holiday Lights Tour hosted by Chicago Trolley & Double Decker Co. The 2.5-hour tour kicks off near the spectacular Christmas tree in front of the towering 875 North Michigan Avenue building (formerly the John Hancock Center), then travels through the Loop past the quaint Christkindlmarket and by the glittering ZooLights display at Lincoln Park Zoo. A free cupcake from Sprinkles makes the trip even sweeter. The trolley makes two stops so visitors can hop off and explore the sights. Private group charters are available.


Copy of navy pier

Head to Navy Pier for the annual Winter WonderFest, held December 1, 2018 through January 6, 2019. Navy Pier is transformed into a 170,000-square-foot indoor winter wonderland with rides and slides, the Chicago Blackhawks Ice Skating Rink, and sparkling holiday decorations that include a forest of nearly 500 Christmas trees. Discounted group tickets are available.. 


Sing in the season during Symphony Center's annual holiday spectacular, featuring members of the Chicago Symphony Orchestra and guest vocalist Storm Large performing festive favorites. Don't be surprised when Santa Claus steps on stage, adding to the merriment. Merry, Merry Chicago! performances are held December 14-23, 2018. Group rates are available.

Find even more ideas for Chicago fall and holiday group fun.

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