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398 Holiday Party Entertainers serving Pleasant Prairie, WI

Featured

Santa Ed

5.0 (7)
Top Performer
17 Verified bookings

  • Mundelein, IL
  • Santa Claus / Holiday Party Entertainment
  • 20 miles from Pleasant Prairie
  • $125 – $200 per hour

Kayla S. said “We could not have asked for a better Santa for our Claus for a Cause event! He was absolutely AMAZING - so warm, friendly, and engaging with every child and family. His communication leading up to the... ”
Featured

Ferny Magic

5.0 (13)
Top Performer
26 Verified bookings

  • Lake Zurich, IL
  • Magician / Holiday Party Entertainment
  • 26 miles from Pleasant Prairie
  • Starts at $400

Brazilio C. said “Everyone had a great time , everyone enjoyed the magic . Thank for a great show. ”
Featured

The Real Santa

4.97 (30)
Top Performer
52 Verified bookings

  • Crystal Lake, IL
  • Santa Claus / Holiday Party Entertainment
  • 29 miles from Pleasant Prairie
  • $75 – $300 per hour

Pat R. said “Santa was a very nice man. He read "The Night Before Christmas" book and led the group in singing "Jingle Bells". He then handed out the stockings we had for all of our kids. He was very... ”
Featured

Zach Michel - Comedy Magician

4.97 (35)
Top Performer
73 Verified bookings

  • Milwaukee, WI
  • Magician / Holiday Party Entertainment
  • 34 miles from Pleasant Prairie
  • $450 – $5,000 per event

Bobbi M. said “Zach did a fantastic job entertaining our diverse group at our company Christmas party. He kept us laughing through the show. I highly recommend booking him for your entertainment needs. ”
Featured

Cocktail Piano Music - Judy Bowen

4.89 (31)
Top Performer
66 Verified bookings

  • Milwaukee, WI
  • Pianist / Holiday Party Entertainment
  • 34 miles from Pleasant Prairie
  • $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

Brenden Trojan

5.0 (27)
Top Performer
39 Verified bookings

  • South Barrington, IL
  • Magician / Holiday Party Entertainment
  • 34 miles from Pleasant Prairie
  • Contact for pricing

James W. said “Brenden did an awesome job for our PBIS reward assembly. He had all the students engaged, and all the magic tricks were appropriate for the ages. We did two separate assemblies, one for K-2 and one... ”
Featured

Santa Chicago

4.78 (83)
Top Performer
202 Verified bookings

  • Wilmette, IL
  • Santa Claus / Holiday Party Entertainment
  • 35 miles from Pleasant Prairie
  • 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

The Premier Santa Group

5.0 (2)
9 Verified bookings

  • Crystal Lake, IL
  • Santa Claus / Holiday Party Entertainment
  • 29 miles from Pleasant Prairie
  • Contact for pricing

Peggy S. said “VERY GOOD KIDS LOVED THEM VERY ENTERTAINING ”
Featured

The Great Boodini

4.80 (15)
27 Verified bookings

  • Arlington Heights, IL
  • Magician / Holiday Party Entertainment
  • 32 miles from Pleasant Prairie
  • Contact for pricing

Dale P. said “The Great Boodini was very engaging annd entertaining! Lots of laughs and amazement by both kids and adults. Even the 2 year old was able to participate in the magic with big smiles. The kids magic... ”
Featured

Total-T Magic by Terrence Hunter

5.0 (9)
19 Verified bookings

  • Glenview, IL
  • Magician / Holiday Party Entertainment
  • 33 miles from Pleasant Prairie
  • Starts at $299

Laura L. said “Kids loved him and parents did too. He was on time, friendly and a great entertainer. ”
Featured

Aleon Piano

1 Verified booking

  • Milwaukee, WI
  • Pianist / Holiday Party Entertainment
  • 34 miles from Pleasant Prairie
  • Starts at $300

I love creating a beautiful and memorable atmosphere through live piano music. I perform for weddings, cocktail hours, dinners, romantic evenings, church...
Featured

The Christmas Carolers, LLC

4.78 (14)
61 Verified bookings

  • Milwaukee, WI
  • Christmas Carolers / Holiday Party Entertainment
  • 34 miles from Pleasant Prairie
  • Contact for pricing

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

Kuj Magic

5.0 (2)
13 Verified bookings

  • Milwaukee, WI
  • Magician / Holiday Party Entertainment
  • 34 miles from Pleasant Prairie
  • $600 – $2,500 per event

Samantha C. said “Kuj Magic was a great addition to our corporate event! Everyone really enjoyed his strolling magic during our cocktail hour and his stage performance. ”
Featured

Dennis Christie MD "Master Deceptionist"

5.0 (51)
121 Verified bookings

  • Des Plaines, IL
  • Magician / Holiday Party Entertainment
  • 36 miles from Pleasant Prairie
  • Starts at $400

Danny C. said “We had a wonderful time with Dennis at the office. We recommend him for any event- large or small. ”
Featured

  • Zion, IL
  • Bartender / Holiday Party Entertainment
  • 9 miles from Pleasant Prairie
  • Starts at $6.95 per guest

Kylee H. said “I cannot recommend Jim and Professional Beverage Service enough. Their bartending services at our wedding were outstanding - throughout the night, Jim checked on my new husband and I and swapped our... ”

IYQ Entertainment

4.85 (24)
Top Performer
66 Verified bookings

  • Des Plaines, IL
  • Magician / Holiday Party Entertainment
  • 36 miles from Pleasant Prairie
  • Contact for pricing

Atul R. said “Nice entertainment with Magic , puppet show and fun Banter with Adults. ”

Santa Jim LLC

1 Verified booking

  • Burlington, WI
  • Santa Claus / Holiday Party Entertainment
  • 19 miles from Pleasant Prairie
  • Starts at $150 per hour

Meet Santa Jim For me, being Santa is about much more than putting on a red suit. Every child who meets Santa Jim deserves to be seen, heard, respected,...

Ed Garcia - Magic & Illusion

4.0 (1)
1 Verified booking

  • McHenry, IL
  • Magician / Holiday Party Entertainment
  • 23 miles from Pleasant Prairie
  • Starts at $400

Ed Garcia is a professional magician known for his engaging performances that captivate audiences of all ages. Ed's journey began in his youth, fostering a deep...

Troubadours of Rhythm

5.0 (1)
1 Verified booking

  • Milwaukee, WI
  • Jazz Band / Holiday Party Entertainment
  • 34 miles from Pleasant Prairie
  • $1,200 – $3,000 per event

Margo A. said “The guys are pros! The band was communicative, ready to play when our event started, and engaged with our guests. The music was PERFECT for a company holiday party. Entertaining, lively, and appealing... ”

Tavern Team

5.0 (6)
13 Verified bookings

  • Milwaukee, WI
  • Bartender / Holiday Party Entertainment
  • 34 miles from Pleasant Prairie
  • Starts at $500

Maraba H. said “We hired Tavern Team for our wedding reception-- we got amazing cocktails and amazing service! Tavern Team consistently went the extra mile to make our reception so fun and special. ”

Santa Ted B

5.0 (17)
Top Performer
32 Verified bookings

  • Gurnee, IL
  • Santa Claus / Holiday Party Entertainment
  • 13 miles from Pleasant Prairie
  • $150 per hour

Susan K. said “We liked Santa Ted so much last year, we hired him again this year. He’s really good with kids and great interacting with everyone! We won’t be in town for the holidays on 2026 but if we were I’d book... ”

North Shore Santa

5.0 (1)
Top Performer
3 Verified bookings

  • Waukegan, IL
  • Santa Claus / Holiday Party Entertainment
  • 14 miles from Pleasant Prairie
  • $100 – $1,200 per event

Rachel M. said “North Shore Santa was very prompt and professional. He was great with kids and adults and made the event very fun. A couple of the kids wanted to keep going back to talk and take pictures with... ”

Jazz Flux

5.0 (1)
Top Performer
4 Verified bookings

  • Milwaukee, WI
  • Jazz Band / Holiday Party Entertainment
  • 34 miles from Pleasant Prairie
  • Contact for pricing

Anne B. said “We were delighted to host the Jazz Flux band at Sacred Heart. Their performance brought energy, joy, and wonderful music to the sisters. The musicians were not only highly skilled but also warm and... ”

Jazz In Vivo

5.0 (2)
Top Performer
3 Verified bookings

  • Milwaukee, WI
  • Jazz Band / Holiday Party Entertainment
  • 34 miles from Pleasant Prairie
  • $200 – $1,000 per event

Kelly B. said “Jazz In Vivo was absolutely amazing. They met my exact jazz performance vision for my event. I am a corporate event planner of 30 years. This was THE BEST jazz band I have ever worked with. ... ”

The Enchanted Carriage

5.0 (13)
Top Performer
22 Verified bookings

  • Eagle, WI
  • Horse Drawn Carriage / Holiday Party Entertainment
  • 36 miles from Pleasant Prairie
  • Contact for pricing

Sara F. said “Enchanted Carriage did an amazing job! They were very responsive, personable, accommodating, and provided the best possible experience for my daughter’s first birthday. I would recommend! ”

Santa David-Kenosha

5.0 (5)
6 Verified bookings

  • Pleasant Prairie, WI
  • Santa Claus / Holiday Party Entertainment
  • $100 – $250 per event

Ruth E. said “David Slama was hired by a friend of ours for a day-long Christmas event, and he was absolutely wonderful. He made every interaction feel special and stayed in character the entire day. He was kind,... ”

LeBoeuf Brothers Magic

1 Verified booking

  • Kansasville, WI
  • Magician / Holiday Party Entertainment
  • 13 miles from Pleasant Prairie
  • Starts at $300

We provide entertainment for kids and adults, Parties of any kind. Corporate events, Weddings, Birthdays, Retirement. We can customize a show for your needs....

Bow Tie Bartenders and Servers

5.0 (10)
11 Verified bookings

  • Racine, WI
  • Bartender / Holiday Party Entertainment
  • 14 miles from Pleasant Prairie
  • Starts at $250

Brazilio C. said “Everything was great , the bar service was smooth and guest were happy. Thank You. ”

Piano Tim Barton

5.0 (4)
10 Verified bookings

  • Grayslake, IL
  • Pianist / Holiday Party Entertainment
  • 15 miles from Pleasant Prairie
  • Starts at $250

Steve I. said “Tim did a terrific job at our memorial. The two specific pieces I requested are not particularly easy piano pieces, and Tim played them both beautifully! He was really easy to work with - a great guy!... ”

Santa Rick

5.0 (3)
5 Verified bookings

  • Round Lake, IL
  • Santa Claus / Holiday Party Entertainment
  • 16 miles from Pleasant Prairie
  • Contact for pricing

Jennifer L. said “Santa Rick made our holiday! He blew us away. He knew our names and brought us much joy. He worked with me in advance on our traditions. All ages loved it. Special memories. Thanks so much! ”

Open Bar Catering

1 Verified booking

  • Fox Lake, IL
  • Bartender / Holiday Party Entertainment
  • 17 miles from Pleasant Prairie
  • Contact for pricing

Open Bar Catering offers Beverage Catering & Bartending Services in Northern Illinois (Aurora, Chicago, Elgin, Joliet, Naperville, Rockford, Waukegan). Open Bar...

Santa Mike K

5.0 (1)
2 Verified bookings

  • Libertyville, IL
  • Santa Claus / Holiday Party Entertainment
  • 19 miles from Pleasant Prairie
  • Contact for pricing

Becky C. said “Santa Mike was the best. The kids loved him. There was one child that didn't want to go near Santa. But Santa Mike's wonderful charm and a bit of coaxing, the child came up to him for a visit. ”

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About booking Holiday Party Entertainment in Pleasant Prairie, WI

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 Pleasant Prairie, Wisconsin 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 Pleasant Prairie 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 Pleasant Prairie, WI area

These Holiday Party Entertainment serve the wider Pleasant Prairie and Kenosha county area and travel to Woodworth, Russell, Bristol, Kenosha, Somers, Winthrop Harbor, Benet Lake, Wadsworth, Paddock Lake, Zion, Salem, Old Mill Creek, Antioch, Beach Park, Trevor, Sturtevant, Camp Lake, Lindenhurst, Union Grove, Lake Villa, Silver Lake, Kansasville, Gurnee, Mount Pleasant, Wilmot, Gages Lake, Waukegan, Racine, Wheatland, and Franksville.

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