Hinsdale magician and mentalist Nick Gasparro performing mind reading for a guest as friends laugh

When Is the Best Time to Book Holiday Party Entertainment? (And What to Do If It’s Already November)

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The best time to book holiday party entertainment is late summer to early fall. That’s when the first two Saturdays of December are still wide open, and when the companies and families who plan ahead are making their calls. But if you’re reading this in November, don’t panic. Plenty of great holiday parties get booked now. You just need to be a little more flexible and a lot more decisive.

Here’s how the holiday booking season actually works in Chicago’s western and southwest suburbs, which dates disappear first, and how to still land the party you want.

The Short Answer

  • Corporate holiday parties: 3 to 5 months ahead (August through October). Companies lock in a banquet room first, then the entertainment.
  • In-home and private holiday parties: 6 to 10 weeks ahead. Hosts often set the date in October or early November.
  • Already November? Book this week if you want a December Friday or Saturday. Weeknights, Sundays and early January stay open longer.

If you’re planning a company event, our company party booking timeline goes deeper on venues and lead times. This post is for everyone else, too: the family get-together, the neighborhood party and the dinner party for twenty.

Which December Dates Go First

Every year the same nights fill up first:

  1. The first two Saturdays in December. They sit right in the sweet spot. It’s late enough to feel like the holidays and early enough that nobody has left town yet.
  2. The Fridays right before them. These are the most popular nights for office parties held after work.
  3. The Saturday a week before Christmas. This one is popular with families and private hosts, less so with companies.

The weekend right before Christmas and the days between Christmas and New Year’s are quieter. A lot of guests are traveling, so many hosts skip them.

November Isn’t Too Late. Here’s How to Make It Work

1. Have two or three dates ready

If your heart is set on one Saturday, have a backup or two. Ask your entertainer which of your dates are still open before you send out invitations. Then send them out right away.

2. Consider a weeknight or a Sunday afternoon

A Thursday-night holiday party is easier for guests than you’d think, and a Sunday afternoon open house works great for families. Venues and entertainers both have more room on these days.

3. Move it to January

More and more suburban companies and friend groups are throwing a “holiday party” in early to mid-January. Calendars are clear, people aren’t burned out, and it gives everyone something to look forward to after the holidays. It’s also the easiest way to get your first-choice date.

4. Decide quickly

In November, the date usually goes to whoever puts down a deposit first, not whoever asked first. If the date is open and the plan fits, lock it in.

What to Know Before You Call

You’ll get a faster, more accurate quote if you have these ready:

  • Date and start time, plus a backup date
  • Town and venue (your home, a restaurant’s private room, the office)
  • Guest count and whether it’s adults only
  • The flow of the night: when people arrive, when you eat, and when you’d like the entertainment

Stand-Up Show or Strolling? Pick the Format That Fits Your Party

For most holiday parties, a magician and mentalist works one of two ways.

A stand-up mind reading show is a featured, 50-minute live show for the whole room, built around audience participation. It turns a party into an event that everyone talks about the next morning. Schedule it after dinner, once guests have finished eating, so you have everyone’s attention.

Strolling magic and mentalism happens during the cocktail hour or open house. The performer moves from group to group, up close. As a rule of thumb, plan about an hour for every 40 to 50 guests so every group gets a real moment.

Many hosts do both: strolling while people arrive, then the show after dinner. You can read more about private and in-home holiday parties or corporate holiday events.

Why Mentalism Works So Well at Holiday Parties

Holiday parties mix people who don’t know each other well: spouses meeting coworkers, in-laws meeting neighbors. Mentalism gives them something to share. The most impossible moments happen in guests’ own heads, so it lands just as well with the people who usually say “I’m not really into magic.” And because it’s built on conversation rather than props, it fits in a living room just as easily as a banquet hall.

Book Holiday Party Entertainment in the Chicago Suburbs

Nick Gasparro is a magician and mentalist based in Oak Brook with more than 25 years of experience, and he was featured on WGN-TV’s Spotlight Chicago. He performs holiday parties throughout DuPage, Will and southwest Cook County, including Naperville, Hinsdale, Downers Grove, Elmhurst, Orland Park and Tinley Park.

December weekends fill quickly. Check Nick’s availability for your date or call 847-773-5306. He responds within 24 hours. A 50% deposit reserves your date.