Group vacation fun in Chicago

Plan an exciting trip to coincide with the dazzling festivities during Chicago's fall and winter holidays. Your group will be impressed by the city's joyful local traditions, from a nighttime Halloween parade and lively craft markets to glittering light shows and classic seasonal performances. Check out our suggestions for group holiday fun in Chicago.


Arts in the Dark, photo by James Richard IV Photography

Arts in the Dark

On October 19, 2024, over 50,000 people are expected to line State Street in the Loop to cheer Arts in the Dark. This Halloween evening parade includes floats, puppets, music, dancing and performers in spectacular costumes. Billed as an “artists' holiday,” the event celebrates the talents of the city's creative community. USA today ranked Arts in the Dark as one of the top 10 Halloween parades in the United States.

Haunted Halloween Parade in Halsted

Come with your group on October 31, 2024 to see the fantastic costumes that will be on display during the Haunted Halloween Parade in Halstednamed after Fodor's as one of the 10 best Halloween parades in the USA The parade moves along Halsted Street in the city's landmark LGBTQ+ Northalsted neighborhood (formerly known as Boystown). Hundreds of participants raise the stakes each year, vying for cash prizes in character, creativity, history, youth and group categories. Stay after the parade to watch the lively awards ceremony.


Chicago Christmas Market

Take your group on a trip to a German Christmas market in the heart of downtown Chicago. The scent of mulled wine, sizzling bratwurst and roasted nuts wafts from the charming wooden stalls along Daley Plaza. Artisans on Chicago Christmas Market Sell ​​colorful ornaments, handmade wooden toys, cozy woven clothing and more. Live music is rousing and admission to the market is free. Ask about group dining and special ticketed events. Christkindlmarket Chicago begins in mid-November and runs through December 24, 2024.

A Christmas Story at The Goodman
A Christmas Carol at the Goodman Theatre

A Christmas song

Watch the holiday classic A Christmas Carol by Charles Dickens from 16 November to 30 December 2024 in Goodman Theatre. Acclaimed actor Larry Yando will reprise his lead role as the bitter, miserly Ebenezer Scrooge who eventually surrenders to the spirit of Christmas. Featuring an incredible set that sees Scrooge flying across the stage, the iconic production is a Chicago Christmas tradition. Reserve tickets now for groups of 15 or more to get the best prices and seating.

ZooLights at Lincoln Park Zoo

Lincoln Park Zoo will be held during the annual ZooLights. Visitors to this evening event, which runs from mid-November to early January, can look forward to a number of holiday experiences. In addition to the zoo's animal exhibits, you can experience dazzling light shows, Christmas carols and costumed characters. Watch ice carvers at work, ride a whimsical carousel or decorate cookies with Mrs. Claus. Ask how you can customize the experience for your group.

Christmas around the world And Holidays of Light

More than 50 trees decorated by volunteers in Griffin Museum of Science and Industry beautifully depict cultural holiday traditions from around the world. The trees surround the glittering four-story Grand Tree, which stretches from the ground floor to the museum's globe. On weekends, you can enjoy live international music and dance performances. Christmas around the world And Holidays of Light can be seen from mid-November to early January. groups Groups of 15 or more receive discounts when booking at least two weeks in advance. Special group activities, guided tours and lunches can be included in your visit.

Skating band for Maggie Daley Park
Skating band for Maggie Daley Park

Skating band for Maggie Daley Park

Downtown Maggie Daley Park becomes every ice skater's dream in winter. Glide along the Skating rinka winding, ice-covered path adjacent to Millennium Park. Reserve a two-hour session in advance to accommodate your group during the skating season from November to March. Skates are available for rental.

Millennium Park

Several events that you cannot miss ring in the holiday season at Millennium ParkOn November 22, 2024, you can join the festivities on Michigan Avenue, which will mark City of Chicago Christmas Tree Lighting Ceremonyfollowed by fireworks lighting up the sky. Visit the Holiday sing-along with choir groups on Friday evenings in December. From November to March, you and your group can lace up rented skates and do a few laps on the outdoor rink. McCormick Tribune Ice Rinkwith the spectacular city skyline in the background.

The Wintrust Magnificent Mile Lights Festival
The Wintrust Magnificent Mile Lights Festival

The Wintrust Magnificent Mile Lights Festival

For over 30 years The Wintrust Magnificent Mile Lights Festival has kicked off the holiday season in Chicago on North Michigan Avenue. Bring your group on November 23, 2024 for a full day of free activities including games, photos with Santa, and booths selling local food and drink. The festival culminates with a parade led by Mickey Mouse and Minnie Mouse, where more than 200 trees along Michigan Avenue are magically illuminated by nearly a million lights. The parade also includes floats, celebrity appearances, marching bands, and Santa himself. A spectacular fireworks display over the Chicago River concludes the day of fun.

Christmas market in Winterland on Gallagher Way
Wrigleyville Christmas Market in Winterland on Gallagher Way

Winterland on Gallagher Way

Go to Gallagher Way in the historical Wrigley Field (Home of the Chicago Cubs baseball team) and discover many ways your group can celebrate the season. Winterland at Gallagher Way brings an ice rink to the famous venue and offers a variety of holiday activities, including Christmas movies and arts and crafts, from late November to early January. Part of the popular event is Wrigleyville Christmas Marketa smaller version of the Christmas market in the city center, with craft stalls and German food.

The Nutcracker

A young girl’s Christmas dream of a magical nutcracker prince, toy soldiers and an army of evil mice comes to life in The Nutcrackera popular annual Christmas performance by the celebrated Joffrey BalletSet during the 1893 Chicago World's Fair, this magnificent production was choreographed by two-time Tony Award winner Christopher Wheeldon and will be performed at the Lyric Opera House from December 6-28, 2024. Discounted seating is available for groups of 10 or more.

Menorah at Daley Plaza
Menorah at Daley Plaza

Celebration of lighting the Menorah

Gather at Daley Plaza in the Loop to witness the lighting of a 31-foot-tall menorah for Hanukkah, the eight-day Festival of Lights. The celebration continues a tradition started by Chabad Center for Jewish Life since 1987. After the lighting, participants dance and eat latkes and doughnuts. The celebration begins on December 25, 2024, and ends on January 2, 2025.

Kwanzaa celebration

Celebrate African American heritage by joining the Kwanzaa celebration with dance, drumming and storytelling at The DuSable Black History Museum and Education CenterThe holiday from December 26, 2024 to January 1, 2025 focuses on the seven principles of Kwanzaa – unity, self-determination, shared work and responsibility, cooperative economics, purpose, creativity and faith.

Discover even more opportunities for your group to Holidays in Chicago.