Christmas Carolers in Chicago, IL
If you’re looking for Christmas carolers in Chicago, IL, near you, Olde Towne Carolers is the city’s trusted source for live holiday entertainment. From downtown corporate parties in the Loop to festive gatherings at iconic spots like Navy Pier and Millennium Park, our professional carolers perform each season with timeless music and elegant Victorian costumes. Whether you’re planning a holiday party at home, hosting a corporate event in Fulton Market, or adding seasonal cheer for shoppers along the Magnificent Mile, Olde Towne Carolers deliver the Christmas spirit with professionalism, warmth, and style.
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We Provide Christmas Carolers in Chicago, IL
and all surrounding areas
SERVICES
available in the entire Chicagoland area
Christmas Carolers
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Learn MoreHere’s What Our Chicagoland Clients Say…
“The carolers made my Christmas party”
“They made my Christmas party. I wished I had booked them for a little longer. Everyone was asking where I found them. They were punctual, pleasant, and in character. They were fantastic! I would highly recommend.”
Marie Rimgaila
“Very professional from start to finish”
“The singers were very professional from start to finish and brought a smile to everyone’s faces. We also loved the Victorian costume! The whole process from booking to payment was super easy and everyone I interacted with was helpful and professional. Would definitely book again!”
Barry James,
No. 7 Beauty Company
“You made my parents’ night”
“Thank you for making my parents’ night with the carol-gram on Saturday! They called us right away to tell us how much they enjoyed it. We appreciate your communication and service! Happy holidays!”
Erin Guard
“Simply magical”
“It was simply magical! The children and adults were all mesmerized by the beautiful voices singing all our favorite Christmas songs. Booking the event was easy and any question I had was answered quickly and thoughtfully. I would highly recommend them for your next event – it’s worth every moment made!”
Laura Greene
“A delight and pleasure, arrived promptly”
“It was a delight and pleasure to have the Olde Towne Carolers at our Holiday Open House. They arrived promptly and ‘roamed’ the house singing to all our guests. I truly like the period costumes and would definitely recommend them to others for their events.”
Sandy Focht
“Amazing! 5 Stars!”
“Amazing! We had a great event!!! 5 stars!”
Ann Saybolt
Olde Towne Carolers: Your Best Choice for Christmas Carolers in Chicago, IL
Chicago is the largest city in Illinois and one of the most dynamic in the country, known for its stunning architecture, rich cultural history, and vibrant neighborhoods stretching from the Loop to the lakefront. Often called the “Windy City,” Chicago is home to Fortune 500 companies, world-class universities, and a thriving arts and dining scene. Each December, the city sparkles with beloved holiday traditions, including the Christkindlmarket at Daley Plaza, the ice skating ribbon at Maggie Daley Park, and dazzling light displays at Lincoln Park Zoo.
With countless corporate parties, private celebrations, and community events across the city, the demand for high-quality live entertainment is strong all season long. Olde Towne Carolers meet that need, performing in authentic Victorian costumes and filling Chicago’s holiday gatherings with music, warmth, and festive cheer.
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Where Our Carolers Perform in Chicago
The Peninsula Hotel
Olde Towne Carolers were invited to perform for a holiday party at the Peninsula Hotel, one of Chicago’s most luxurious five-star destinations. Our carolers added festive cheer to the celebration with live Victorian-costumed singers, creating a holiday atmosphere guests won’t forget. High-end hotels across Chicago, from the Palmer House Hilton to the Waldorf Astoria, host corporate and private holiday parties throughout December — and our professional carolers are the perfect entertainment choice for these elegant gatherings.
Google HQ at Fulton Market
Our singers brought festive music and Victorian charm to a holiday celebration for Google at their Chicago headquarters in the vibrant Fulton Market District – showing how live carolers can transform a workplace party into a memorable experience. Across Chicago, leading companies like United Airlines, Boeing, and McDonald’s host holiday events where professional entertainment sets the tone — and Olde Towne Carolers are a trusted choice for adding holiday joy to corporate events.
Damen Avenue in Wicker Park
Our carolers were photographed spreading holiday cheer along Damen Avenue, one of Chicago’s most vibrant shopping and dining districts. With its boutiques, restaurants, and neighborhood gatherings, Damen becomes a festive hub during the holiday season, making live caroling the perfect addition. Olde Towne Carolers often provide background music for seasonal events in districts like Wicker Park, Bucktown, and Lincoln Park, creating a joyful soundtrack for the holiday experience.
Magical Christmas in Chicago!
Olde Towne Carolers bring festive sparkle to holiday parties and events across Chicago. Hosts often tell us our music is the highlight their guests remember the most. With rich harmonies and elegant Victorian attire, our singers capture the timeless spirit of Christmas and make every celebration feel truly special.
Get a QuoteShow-Stopping Sound and Style
Our classically trained singers and picture-perfect costumes instantly elevate your celebration. The result is a Christmas atmosphere so festive and photogenic that guests feel transported to a simpler time — and your party or event feels truly special.
see our photosFlexible Performances, Everywhere
From strolling carolers mingling with guests to a featured stage moment, we adapt effortlessly to your space and schedule – even outdoors! You can relax, knowing the music will fit your vision and keep the night flowing beautifully.
watch our videosTrusted. Year After Year.
Families, companies, and iconic venues book us again and again for one reason: peace of mind. With 20 holiday seasons under our belt, our belief in punctual arrivals and smooth planning mean you can enjoy your event instead of managing it.
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Why Chicago Chooses Olde Towne Carolers
Since 2005, Olde Towne Carolers has built a reputation as a premier name in live holiday entertainment. Our Chicago ensemble extends that tradition, bringing festive music and Victorian charm to corporate parties, community events, and private gatherings throughout the city. With the support of a company known for professionalism and glowing reviews, Olde Towne Carolers make holiday celebrations in the Windy City memorable year after year.
In addition to Philly, we also offer Christmas Carolers in Evanston, IL and Christmas Carolers in Oak Brook, IL. No matter where you are in the Delaware Valley, we can entertain you!
21 Years in Business
Professional Musicians
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Hundreds of Reviews
Large Company
International Clients
National TV Appearances
CDs Available
Appearances with Recording Artist
