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428 Holiday Party Entertainers serving Highland, IN

Featured

Street Magician Norman Basile

5.0 (94)
Top Performer
128 Verified bookings

  • Hobart, IN
  • Magician / Holiday Party Entertainment
  • 10 miles from Highland
  • $280 – $1,000 per event

Rachel S. said “We had Norman for a bachelorette party and he did not disappoint! We were in awe the entire time! Fantastic show and very passionate! ”
Featured

Santa Wayne

5.0 (34)
Top Performer
54 Verified bookings

  • Tinley Park, IL
  • Santa Claus / Holiday Party Entertainment
  • 18 miles from Highland
  • Contact for pricing

Lauren V. said “Santa Wayne was perfect for my daughter’s 7th birthday party. He showed up right on time with a big smile and made all the kids laugh through their silly questions. Definitely recommend Santa Wayne! ”
Featured

Cocktail Piano Music - Judy Bowen

4.89 (31)
Top Performer
66 Verified bookings

  • Chicago, IL
  • Pianist / Holiday Party Entertainment
  • 24 miles from Highland
  • $200 – $1,500 per event

Whitney M. said “Judy was a pleasure to work with. We will be hiring her again for our next Vegas function.”
Featured

Markus Rutz Music

5.0 (12)
Top Performer
23 Verified bookings

  • Chicago, IL
  • Jazz Band / Holiday Party Entertainment
  • 24 miles from Highland
  • Starts at $300

Maggie M. said “The Markus Rutz Jazz Quartet delivered an exceptional performance at our UIH Night event, elevating the entire evening with their artistry, professionalism, and dynamic musical presence. From the very...”
Featured

The American Caroling Company

4.80 (92)
Top Performer
179 Verified bookings

  • Chicago, IL
  • Christmas Carolers / Holiday Party Entertainment
  • 24 miles from Highland
  • Starts at $450

Katie P. said “What a great night. The American Caroling Company really added the perfect touch of Christmas spirit to our event. The communication was fabulous. The group arrived on time. Our guest very much...”
Featured

Mario Dueñas

5.0 (24)
Top Performer
33 Verified bookings

  • Chicago, IL
  • Jazz Band / Holiday Party Entertainment
  • 24 miles from Highland
  • Contact for pricing

Sarah L. said “I had my wedding at Adler Planetarium in Chicago and wanted to have an excellent music experience to top off the wedding. Mario is a wonderful musician. Being a classical pianist, music was one of the...”
Featured

Prestige Performances

4.91 (128)
Top Performer
283 Verified bookings

  • Chicago, IL
  • Jazz Band / Holiday Party Entertainment
  • 24 miles from Highland
  • $450 – $10,000 per event

Shelia H. said “Awesome performance… the ultimate professional. ”
Featured

The Lola Bard Holiday Carolers

5.0 (26)
Top Performer
65 Verified bookings

  • Chicago, IL
  • Christmas Carolers / Holiday Party Entertainment
  • 24 miles from Highland
  • Starts at $500

Gautam K. said “Loved having the carolers at our Christmas party - added a festive touch to the get together and they were very nice”
Featured

Magician Dan Feltey

5.0 (10)
Top Performer
10 Verified bookings

  • Chicago, IL
  • Magician / Holiday Party Entertainment
  • 24 miles from Highland
  • Contact for pricing

Sarah G. said “Dan performed at our Halloween party for a group of over 20 people and did a fantastic job! There was a good mix of props/cards/mentalist tricks. Everyone was amazed, and he did a great job with crowd...”
Featured

Olde Towne Carolers

5.0 (14)
Top Performer
34 Verified bookings

  • Chicago, IL
  • Christmas Carolers / Holiday Party Entertainment
  • 24 miles from Highland
  • Contact for pricing

Kurt K. said “Absolutely fantastic! Beautiful voices.”
Featured

The John Behling Group

5.0 (6)
Top Performer
12 Verified bookings

  • Chicago, IL
  • Jazz Band / Holiday Party Entertainment
  • 24 miles from Highland
  • $450 – $3,000 per event

Abby A. said “It was a pleasure working with the John Behling Group, communication was easy and seamless and the music was a great background for our elegant event. We received many compliments about the band...”
Featured

Bmr4

5.0 (20)
Top Performer
54 Verified bookings

  • Chicago, IL
  • Jazz Band / Holiday Party Entertainment
  • 24 miles from Highland
  • $400 – $2,500 per event

Amy P. said “I hired Bmr4 to perform at a private memorial reception for my father and they were terrific! I wanted move our guests into a celebration of his life after the funeral mass and the beautiful jazz...”
Featured

Mr. Lucky and his Orchestra of Tomorrow!

5.0 (2)
Top Performer
1 Verified booking

  • Chicago, IL
  • Jazz Band / Holiday Party Entertainment
  • 24 miles from Highland
  • $1,000 – $8,000 per event

Jessica E. said “Mr. Lucky and his Orchestra of Tomorrow are a group of very talented musicians who are also down-to-Earth. Whether you want them to keep the dance floor hopping as others watch and enjoy the show,...”
Featured

Michael the Santa

5.0 (7)
Top Performer
30 Verified bookings

  • La Grange Park, IL
  • Santa Claus / Holiday Party Entertainment
  • 29 miles from Highland
  • Contact for pricing

Logan L. said “Amazing improv, extremely kind and easy to work with, such a good heart, and embodied the sweet and jolliness of Santa. Would hire again, and again.”
Featured

Santa Chicago

4.78 (83)
Top Performer
202 Verified bookings

  • Wilmette, IL
  • Santa Claus / Holiday Party Entertainment
  • 38 miles from Highland
  • Starts at $40 per hour

Amanda G. said “He was awesome! We received many compliments on him. He was great with the kids. I would definitely recommend. I am hoping to book again for next year! Thank you! ”
Featured

Santa Claus Irwin

4.84 (25)
Top Performer
62 Verified bookings

  • Naperville, IL
  • Santa Claus / Holiday Party Entertainment
  • 39 miles from Highland
  • Contact for pricing

Nayeli N. said “Best Santa ever!!! ”
Featured

The Frozen Robins/Mingle with the Kringles

5.0 (39)
104 Verified bookings

  • Chicago, IL
  • Santa Claus / Holiday Party Entertainment
  • 24 miles from Highland
  • $60 – $5,000 per event

Barb H. said “We had a fun and engaging visit with Santa and Mrs Claus. They interacted with the children and we sang Christmas carols. We will definitely look forward to having them visit again next year!”
Featured

IL Suono Music Agency

4.92 (39)
59 Verified bookings

  • Chicago, IL
  • Pianist / Holiday Party Entertainment
  • 24 miles from Highland
  • Contact for pricing

Rodney F. said “A-Z IL Suono delivered The performer was on time. Played beautifully, he even took a request. We couldn’t have been happier. We’d definitely use them again. Great Job! Thanks”
Featured

Windy City Santa

5.0 (7)
24 Verified bookings

  • Chicago, IL
  • Santa Claus / Holiday Party Entertainment
  • 24 miles from Highland
  • Starts at $125

Sarah A. said “Santa Matt did a great job at my client event. Was wonderful with the kids, played the part well, and even engaged with the adults. Would recommend him again! ”
Featured

Windy City Strings

4.84 (27)
48 Verified bookings

  • Chicago, IL
  • Classical Ensemble / Holiday Party Entertainment
  • 24 miles from Highland
  • Starts at $200

Melissa J. said “What a treat to have Windy City Strings play for our Christmas Party! Our employees loved it, and we would definitely book them for an event again. Thank you! Melissa”
Featured

The Jazz Arts Duo

4.95 (18)
29 Verified bookings

  • Chicago, IL
  • Jazz Band / Holiday Party Entertainment
  • 24 miles from Highland
  • $500 – $2,000 per event

Bob M. said “This is the second time we engaged the Jazz Arts Duo for a party. They were excellent! John and Marcel kept the music interesting. Our guests, many of whom were affiliated with the musical arts, ...”
Featured

Louis Pettinelli Entertainment

4.92 (70)
249 Verified bookings

  • Chicago, IL
  • Jazz Band / Holiday Party Entertainment
  • 24 miles from Highland
  • Starts at $300

Kelly S. said “Hired for our corporate event. They did a fantastic job from communication to execution to performance. Thanks!”
Featured

Dr. Dave Magic

5.0 (96)
115 Verified bookings

  • Chicago, IL
  • Magician / Holiday Party Entertainment
  • 24 miles from Highland
  • Contact for pricing

Madison S. said “Dr. Dave was absolutely amazing. I expected a magician, but Dr. Dave was a whole performance. He blew us all away, he was also hilarious, very professional, and showed up right on time. I would hire...”
Featured

Mega Magic- Magician Mike D'Urzo

5.0 (23)
23 Verified bookings

  • Chicago, IL
  • Magician / Holiday Party Entertainment
  • 24 miles from Highland
  • Contact for pricing

Kristina T. said “Mike put on an awesome show. He was punctual, prepared and very organized. He was engaging with the crowd and was just an absolute pleasure to be around. Everyone was amazed by his talent. Fun was...”
Featured

The Christmas Carolers, LLC

4.78 (14)
61 Verified bookings

  • Chicago, IL
  • Christmas Carolers / Holiday Party Entertainment
  • 24 miles from Highland
  • Contact for pricing

Pete H. said “The Christmas Carolers were outstanding. Their singing brought alot of the Christmas Spirit to our Christmas Party. ”
Featured

Harrison Jazz Ensemble

4.71 (30)
61 Verified bookings

  • Chicago, IL
  • Jazz Band / Holiday Party Entertainment
  • 24 miles from Highland
  • $1,000 – $2,500 per event

Odelia K. said “We are very picky with jazz music so we requested lots of different accommodations, which the band were very supportive of. The music was great and all the guests enjoyed the music during our...”
Featured

Hmg+

5.0 (1)
2 Verified bookings

  • Chicago, IL
  • Waitstaff / Holiday Party Entertainment
  • 24 miles from Highland
  • Contact for pricing

Michael A. said “The party was great. Had a very good time. Had 2 waitstaff at the party and they were great. Timely, efficient, helpful, communicative, etc. Would hire again for sure.”
Featured

Chicago Diamond Trio

5.0 (9)
14 Verified bookings

  • Chicago, IL
  • Jazz Band / Holiday Party Entertainment
  • 24 miles from Highland
  • Starts at $300

Mona M. said “The jazz trio with Clark, Josh, and the amazing pianist were perfect for our professional association's holiday party. Communication was straightforward prior to the event, and the musicians were...”
Featured

The Perfect Mix

5.0 (21)
10 Verified bookings

  • Chicago, IL
  • Bartender / Holiday Party Entertainment
  • 24 miles from Highland
  • $50 – $100 per event

David M. said “Joey was wonderful and extremely professional in coming to assist us as an extra bartender at a brewery for our wedding reception. He was able to serve wine and seltzers for us when the venue...”
Featured

Santa Stephen

4.67 (3)
6 Verified bookings

  • Brookfield, IL
  • Santa Claus / Holiday Party Entertainment
  • 28 miles from Highland
  • Starts at $225

Liam B. said “Santa was on time, very friendly and patient with the children. Would definitely hire him again. Thanks!”
Featured

Santa Stops By - By Funtime Services

4.86 (14)
61 Verified bookings

  • Naperville, IL
  • Santa Claus / Holiday Party Entertainment
  • 39 miles from Highland
  • $75 – $2,000 per event

Cinthia F. said “Santa was great, he played the piano and sang carols. The way he went about giving out the gifts was fun. Then when he read The Night Before Christmas the kids all had their eyes glued to him. It...”
Featured

John Measner Magic Productions, Inc.

5.0 (1)
5 Verified bookings

  • Naperville, IL
  • Magician / Holiday Party Entertainment
  • 39 miles from Highland
  • Contact for pricing

Esther B. said “I only have amazing things to say about John! I just got off the phone with him, he was so friendly and helpful, fun and very very experienced, with over forty years! With a show that includes dogs...”

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About booking Holiday Party Entertainment in Highland, IN

The holidays offer special opportunities to create joy and connection with people you care about the most, and the right entertainment can make your celebration truly shine. From Christmas carolers setting a festive mood to Santas delighting children or DJs keeping the dance floor busy, professional entertainers bring the magic that makes a party memorable. Whether you’re planning a large corporate holiday party or a cozy family Christmas party, you can find the right performer to help you create unforgettable moments.

The cost of hiring holiday party entertainers in Highland, Indiana will vary depending on the type of holiday entertainment, their experience, and the length of the performance. A short Santa visit at your family Christmas party will cost less than a live band performing at a holiday corporate event. Contact the local entertainers above to discuss your event details and receive a customized quote.

As you search for Highland holiday party entertainers, view their profiles to read about their services, browse photos, and watch promotional videos. Then, check out reviews from past clients to see what it would be like to work with them. When requesting a quote, include key details like the venue, audience size, expected performance time, and event goals to ensure you receive the most accurate pricing.

Once you find the holiday act you want to hire, finalize the booking on GigSalad. Our full-service platform makes it easy to book holiday party entertainers. You can message the performers, confirm the details of your agreement, and make a secure payment all in one place. Every GigSalad event is covered by our Worry-Free Guarantee, so you can rest easy knowing we’ve got your back. Just relax and let the holiday magic unfold!

Holiday Party Entertainment serving the Highland, IN area

These Holiday Party Entertainment serve the wider Highland and Lake county area and travel to Griffith, Munster, Hammond, Lansing, Schererville, Dyer, Calumet City, Lynwood, East Chicago, Gary, St John, Sauk Village, Glenwood, Merrillville, Ford Heights, Burnham, Thornton, South Holland, Wolf Lake, Whiting, Dolton, Chicago Heights, Phoenix, Hobart, Crown Point, Homewood, Harvey, Riverdale, Lake Station, and Steger.

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