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The 44 Best Holiday Entertainers for Hire in Chicago, IL

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  • Holiday Entertainment
87 Holiday Entertainers serving Chicago, IL
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How it works (it’s simple!)

Browse vendors

1. Browse Holiday Entertainers in Chicago and contact your favorites

Communicate

2. Communicate with the Holiday Entertainment you select to work out the details of your event

Book!

3. Book them through GigSalad and be covered by our 100% awesome guarantee!

Holiday Entertainment Pricing

Pricing

Using data from quotes sent through GigSalad, we’ve gathered average pricing for hiring Holiday Entertainment in your region.

Our Worry-Free Guarantee

Worry-Free Guarantee

Booking a Chicago Holiday Entertainer through GigSalad offers you extra protection you can’t get anywhere else. You can rest easy knowing that your payment is secure, and that we’ll have your back in the event of any trouble that may occur. Learn more

What Chicago Users Say

5-star review

“Amazing and Professional” – Sara S., reviewing Naperville Holiday Entertainer Chezaday Magic Show. More reviews

Piano Bar Cabaret & Open Mic Party - Holiday Entertainment in Chicago, Illinois

This vendor provides virtual services Offers Virtual Services

Piano Bar Cabaret & Open Mic Party - Holiday Entertainment in Chicago, Illinois

Piano Bar Cabaret & Open Mic Party

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0 (0)
  • Map pin icon Chicago, IL
  • Vendor category icon Holiday Entertainment

Holiday Christmas House & Corporate Parties! Exquisite Ambiance Music & Performance! Enjoy Virtuosic Classical, Jazz & Popular Songs throughout the…

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Tyler Fowler - Comedian / Holiday Entertainment in Chicago, Illinois Featured vendor banner

This vendor provides virtual services Offers Virtual Services

Tyler Fowler - Comedian / Holiday Entertainment in Chicago, Illinois

Tyler Fowler

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4.95 (51)
Top Performer badge
  • Map pin icon Chicago, IL
  • Vendor category icon Comedian / Holiday Entertainment
  • Check mark icon 43 Verified Bookings

Jessica W. said “We booked Tyler for a 1 hour show at our house for a party and I would highly recommend anyone to book him. Tyler had us all laughing the entire hour…”

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Matt Griffo - Singing Pianist / Holiday Entertainment in Chicago, Illinois Featured vendor banner

This vendor provides virtual services Offers Virtual Services

Matt Griffo - Singing Pianist / Holiday Entertainment in Chicago, Illinois

Matt Griffo

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5 (32)
Top Performer badge
  • Map pin icon Chicago, IL
  • Vendor category icon Singing Pianist / Holiday Entertainment
  • Check mark icon 48 Verified Bookings

Kim K. said “Matt was very easy to work with from the beginning. He is a highly talented musician who plays a variety of music. He was very sociable with guests and…”

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Chicago Piano by Andy - Pianist / Holiday Entertainment in Chicago, Illinois Featured vendor banner

This vendor provides virtual services Offers Virtual Services

Chicago Piano by Andy - Pianist / Holiday Entertainment in Chicago, Illinois

Chicago Piano by Andy

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4.68 (17)
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  • Map pin icon Chicago, IL
  • Vendor category icon Pianist / Holiday Entertainment
  • Check mark icon 32 Verified Bookings

Mark E. said “Andy was great! We loved having him play at our event!”

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Santa Chicago - Santa Claus / Holiday Entertainment in Wilmette, Illinois Featured vendor banner

This vendor provides virtual services Offers Virtual Services

Santa Chicago - Santa Claus / Holiday Entertainment in Wilmette, Illinois

Santa Chicago

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4.85 (58)
Top Performer badge
  • Map pin icon Wilmette, IL
  • Vendor category icon Santa Claus / Holiday Entertainment
  • Travel distance icon 14 miles from Chicago
  • Check mark icon 119 Verified Bookings

Caleb J. said “He was super professional and highly recommend”

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Chezaday Magic Show - Children’s Party Magician / Holiday Entertainment in Naperville, Illinois Featured vendor banner
Chezaday Magic Show - Children’s Party Magician / Holiday Entertainment in Naperville, Illinois

Chezaday Magic Show

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4.96 (106)
Top Performer badge
  • Map pin icon Naperville, IL
  • Vendor category icon Children’s Party Magician / Holiday Entertainment
  • Travel distance icon 28 miles from Chicago
  • Check mark icon 1 Verified Booking

Sara S. said “Steve was very crowd pleasing and everyone loved the acts he performed. I would recommend him for any event you are hosting! Steve was very flexible and…”

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Dennis Christie MD "Master Deceptionist" - Magician / Holiday Entertainment in Lake Forest, Illinois Featured vendor banner

This vendor provides virtual services Offers Virtual Services

Dennis Christie MD "Master Deceptionist" - Magician / Holiday Entertainment in Lake Forest, Illinois

Dennis Christie MD "Master Deceptionist"

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5.0 (23)
Top Performer badge
  • Map pin icon Lake Forest, IL
  • Vendor category icon Magician / Holiday Entertainment
  • Travel distance icon 28 miles from Chicago
  • Check mark icon 59 Verified Bookings

Molly C. said “Denise is very flexible and he adjusted his performance to fit our needs. He is good with kids and excellent with close up magic. The party guests were…”

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Santa Scott - Santa Claus / Holiday Entertainment in St Charles, Illinois Featured vendor banner
Santa Scott - Santa Claus / Holiday Entertainment in St Charles, Illinois

Santa Scott

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5.0 (18)
Top Performer badge
  • Map pin icon St Charles, IL
  • Vendor category icon Santa Claus / Holiday Entertainment
  • Travel distance icon 35 miles from Chicago
  • Check mark icon 32 Verified Bookings

Joan W. said “Santa Scott was the best Santa ever - great with the kids - patient and jolly! We used him for two days of Santa Mini sessions and he did great the whole…”

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The Chicagoland Duo - Christmas Carolers / Holiday Entertainment in Chicago, Illinois Featured vendor banner

This vendor provides virtual services Offers Virtual Services

The Chicagoland Duo - Christmas Carolers / Holiday Entertainment in Chicago, Illinois

The Chicagoland Duo

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5.0 (10)
  • Map pin icon Chicago, IL
  • Vendor category icon Christmas Carolers / Holiday Entertainment
  • Check mark icon 17 Verified Bookings

Tracy R. said “Great”

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Christmas Carolers Corporate Entertainment Easter Bunnies Family Entertainment Holiday Party Entertainment Mardi Gras Entertainment Mrs. Clauses Santa Clauses Singing Telegrams Storytellers Variety Entertainers

Quick facts
Holiday Entertainment in Chicago, IL

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1,514 quotes sent

In the past year, Holiday Entertainers have sent 1,514 quotes to event planners

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104th most popular

Holiday Entertainers rank #104 in popularity out of 545 categories on GigSalad

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5 out of 5 stars

3,434 Holiday Entertainer reviews on GigSalad with an average rating of 5 stars

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Typically hired for

Retirement Community Events, Corporate Events, and Virtual Events in Chicago

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Chicago ranks #1

for Holiday Entertainer requests in Illinois

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1.3 days on average to book

From request to booking, it takes 1.3 days (on average) to hire a Holiday Entertainer

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Illinois ranks #4

for Holiday Entertainer requests in the United States

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Holiday Entertainment in Chicago, IL


Throughout the year, special holidays create opportunities for us to celebrate with our friends, family and co-workers. If you are planning a memorable holiday party, search our database of performers to book holiday entertainment. Holidays often serve as reminders of important events in our nation's history, other times they are important religious celebrations, and at other times they are simply reasons to connect with friends and family in a party setting. Whatever the case, GigSalad has the talent you need for your private or corporate holiday party.

Check out these examples of often celebrated holidays: Cinco De Mayo, Easter, Memorial Day, Mother's Day, Saint Patrick's Day, Father's Day, Independence Day, Halloween, Labor Day, Oktoberfest, Thanksgiving, Veteran's Day, Chinese New Year, Christmas, Hanukkah, Kwanzaa, Mardi Gras, New Year's Eve and Valentine's Day. And even if you're wanting to celebrate a holiday that's not listed here, you'll be sure to find some exciting entertainment for your event right here on GigSalad! Search for Holiday Entertainment in Chicago, Illinois above.

Please note that these Holiday Entertainment may also travel to Stickney, Forest View, North Riverside, River Forest, Lincolnwood, Riverside, Amf Ohare, Lyons, Hines, Harwood Heights, River Grove, Summit Argo, Summit, Hometown, Broadview, Norridge, McCook, Bedford Park, La Grange Park, Stone Park, Schiller Park, Merrionette Park, Northlake, Hodgkins, Hillside, Berkeley, Justice, Chicago Ridge, Rosemont, and Hickory Hills.

Find Holiday Entertainment in nearby cities

Lincoln Park Cicero Irving Park Oak Park Berwyn Forest Park
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