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Where to go Christmas Caroling in Chicago, IL

by | Nov 18, 2022 | Local

People who go Christmas caroling carry on an oral tradition of spreading Christmas cheer. Singing Christmas carols is a way of telling the story of the nativity and the birth of Jesus Christ while getting others in the festive spirit. To help you get in the spirit of the Christmas holiday in the Chicago, Illinois, area, bundle up, grab some friends, and head to any of these fabulous places to go caroling.

Millennium Park Holiday Sing-Along

Carolers by Joe Lewis is licensed with CC BY-SA 2.0

Head to Millennium Park to Cloud Gate for one of Chicago’s biggest holiday festivities, the Millennium Park Holiday Sing-Along. This event features community singers and chorus groups from across the city, and you’re invited to sing along to your favorite Christmas carols and songs. At this fun and festive event, you’ll enjoy the backdrop of shimmering Christmas lights, Cloud Gate, and the Chicago skyline. Enjoy dinner at one of the many restaurants before heading over to Cloud Gate for the sing-along.

Location: 201 E Randolph St.

Dates: Every Friday from November 25 through December 16, 2022

Time: From 6 p.m. to 7 p.m.

Light Up the Lake at Navy Pier

Everyone in the family will enjoy the fabulous festivities and activities at Chicago’s Light Up the Lake, formally called the Winter WonderFest. The staff at Navy Pier transforms the 170,000-square-feet Festival Hall into a holiday spectacle with over 500 Christmas trees, an interactive light display, and Christmas decorations throughout.

The family can join in the caroling, go ice skating, have fun on the giant slides, and enjoy the carnival rides. With your ticket purchase, you can ride the Centennial Wheel, jump in the Snowman Bouncer, challenge yourself on the Ice Peaks Climbing Walls, and visit the Candy Cane Lighthouse. A visit to Light Up the Lake is the perfect time for your kids to have their picture taken with Santa Claus when he visits between December 1 and December 24.

Location: Navy Pier at 600 E. Grand Ave.

Dates: November 26 through January 2, 2022

Time: For the first two weeks, the event is open from 3 p.m. to p.m. 5 p.m., and for the last two weeks, it’s open from 10 a.m. to 10 p.m. It’s also open on Christmas Eve from 10 a.m. to 5 p.m. and is closed on Christmas Day.

Christkindlmarket at Daley Plaza

You’ll feel like you’re on a European vacation when you stop by Christkindlmarket at Daley Plaza. This German Christmas market and festival is sure to get you in the holiday spirit with plenty of food and activities on offer. As you wander through the market, you’ll smell roasted nuts, freshly baked pretzels, cooked bratwurst, and hot spiced wine. There’s caroling, sparkling Christmas lights, and vendors selling hand-crafted products. Shopping at Christkindlmarket is the perfect way to find gifts for everyone on your holiday shopping list.

Location: Daley Plaza at 50 W. Washington St.

Dates: November 18 through December 24, 2022

Times: Sundays through Thursdays from 11 a.m. to 8 p.m. and Fridays and Saturdays from 11 a.m. to 9 p.m.

ZooLights at the Lincoln Park Zoo

Enjoy being dazzled by all the lights at ZooLights Presented By ComEd and Invesco QQQ and held at the Lincoln Park Zoo. You can purchase tickets to go on the AT&T Endangered Species Carousel, the Lionel Train Adventure, and the Ferris Wheel while wearing 3D HoloSpex glasses, or you can work your way through the Light Maze. You’ll want to keep those 3D glasses handy when you go through the maze.

As you wander through the zoo, you’ll see hundreds of themed light displays, join singing with the roaming Christmas carolers on Sundays before December 25, and get your photo taken with Santa before December 23. You can also watch awe-inspiring live ice carving events, buy holiday gifts, and warm up with hot beverages and tasty holiday snacks.

Location: Lincoln Park Zoo at 2001 N. Clark St.

Dates: November 19 through 23, November 25 through 30, and December 2 through 14, 16–23, and 26–31. The zoo is also open on January 1, 2023.

Times: 4:30 p.m. through 10 p.m.

Wintrust Magnificent Mile Lights Festival

Bring your friends and family to the wondrous Wintrust Magnificent Mile Lights Festival for a day and evening of cheerful holiday spirit, music, and song. This extravaganza takes place on the mile-long Michigan Avenue with festivities galore. The festival’s volunteer team lights and decorates the trees along the street, and as you stroll along, you can shop for holiday gifts, take part in fun family activities — including caroling — and eat foods to keep you fueled up for the main event — the parade.

The parade, with colorful floats, giant holiday-themed helium balloons, Santa Claus, marching bands, celebrities, and musical performances, starts at 5:30 p.m. Kids and adult alike will clap their hands with glee when they see Mickey and Minnie Mouse lead the parade down the Magnificent Mile.

Location: Michigan Avenue

Date: November 19, 2022

Time: 11 a.m. through 5:30 p.m. with the parade finale

Winterland at Gallagher Way

You can ice skate, sing Christmas carols, try curling, and get a thrill with on-ice bumper cars when you visit Winterland at Gallagher Way. Kids will have a blast having breakfast with Santa Claus, making holiday wreaths, and attending Santa’s workshop. The ice rink is inside the Wrigley Field ballpark, and outside along the streets, you’ll find a miniature version of the Christkindlmarket with German and international holiday food.

You won’t go hungry or thirsty at this event, as restaurants, bars, and coffee shops line the decorated streets. Neighboring Hotel Zachary is also offering special holiday programs and family-friendly activities to take part in.

Location: 3635 N. Clark St.

Dates: November 18 through January 8, 2022

Times: 4 p.m. to 10 p.m.

There you have Spot Migration’s list of the best places to go Christmas caroling in the Chicago area. Where’s your favorite place to go, and why? Do you know of any other spots that are perfect for caroling with friends or family? If so, please let us know. We always enjoy discovering more festive locations in our wonderful city.


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