Reconnecting with friends, family and that childlike sense of wonder is what makes the holidays so special. There are also so many things to do in a short amount of time: gifts to buy, events to plan, parties to throw and attend, all on top of an already packed schedule. How can you be sure to reconnect with the magic of the holiday season? That’s where The Caroling Connection can help.
Contact The Caroling Connection
What is The Caroling Connection
The Caroling Connection is a Chicago-area group of Dickensian-costumed a cappella singers who sing four-part holiday songs to provide an almost magical experience to our audience, helping to make holiday memories that last a lifetime. We’re trained musicians of the highest quality, with experience to match, that add that little something extra when you hear and see us sing. Some of the ways to use us are:

- Caroling at your front door to welcome your guests
- Strolling
- Table to table at events or company dinners
- Through a Reception or Cocktail Hour
- From store to store while your patrons are shopping
- Throughout your company holiday party
- Perform a set on a stage for events or meetings
- Sing for your family holiday get together for that special something extra
- That surprise that no one is expecting
- …And more
The Caroling Connection provides an almost magical experience for our audience. As the premier Dickensian Christmas Carolers in the Chicago area, we help create holiday memories that last a lifetime.
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Check The Caroling Connection’s Availability
How we create that experience
The Music
The foundation of The Caroling Connection is music and musicianship. We use a select group of highly educated musicians with degrees in music as well as being highly trained singers. This is the foundation which all carolers will share, simply as a starting point. We will build on that foundation to provide the experience we strive to achieve.
Interacting with the audience

We strive to make the audience feel like family and hopefully have that returned to us from the audience as well. Our live performances are more than a concert. We provide entertainment that goes beyond the music, making our audience feel as if they are a part of the performance itself. We are a cohesive group that works together to meet and at every opportunity exceed our standards and goals. Each caroler is important to the group and therefore to the success of the group. Based on that, we have the ability to bring our audience into our group and feel as if they are a part of the larger Caroling Connection family. Our performances are meant to be fun and uplifting for everyone involved, including you as our client, our audience, and the carolers.
What to expect from The Caroling Connection
On the day(s) of the performance:
- We will arrive 30 minutes before our start time
- We take a 10-minute break as a group after the first hour and every hour after that we are scheduled to sing, included within contracted performance time. (i.e. one break for two hours, two per three hours)
- We take requests, within reason and if we have the music
- We interact with your guests (or not, if you prefer)
- We love to be a part of your pictures
What The Caroling Connection needs from you
On the day(s) of the performance:
- A contact person for the performance (someone to check in with, contact in case of emergency or any other issues that may arise)
- A changing room (which can double as our meeting/break room)
- Any special information/instructions, for example
- Entrance codes to doors
- Best way to get to the performance area
- Traffic paths that need to be kept clear
- If there’s a special highlight of the event/performance, do you need us at a specific place at a specific time during the performance, etc.
Other considerations
The Caroling Connection books through With A Voice Like This. With A Voice Like This maintains a Commercial General Liability Insurance policy insured by Nationwide Mutual Insurance with an A.M. Best Rating of A+ which covers The Caroling Connection with the following limits:
- $1,000,000.00 per occurrence
- $2,000,000.00 aggregate per year
Please request any Additional Insured Endorsements if needed as soon as possible as it can take up to seven (7) business days for the endorsements to be added.
These things aren’t required, but they are nice to know before The Caroling Connection arrives:
- Is parking provided for The Caroling Connection at your location
- Is water available during our breaks
The Caroling Connection’s goal
Our goal is to create an atmosphere of warmth, joy, and wonder that is a part of the holidays for your special event, party or business that will make a lasting memory for everyone involved.
You can contact Jim Goodrich at [email protected], call him at 630.492.0487 to check availability and pricing or use our form below.