- Elgin, IL
- Balloon Twister / Outdoor Party Entertainment
- 21 miles from Woodstock
- $125 per hour
Anna Y. said
“Professional and great at creating all types of animals ”
The 71 Best Outdoor Party Entertainers for hire in Woodstock, IL
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316 Outdoor Party Entertainers serving Woodstock, IL
- Rockford, IL
- Balloon Twister / Outdoor Party Entertainment
- 33 miles from Woodstock
- Contact for pricing
Nick M. said
“It was a pleasure working with Grandma Bingo and the students had tons of fun with her ballon crafts. Highly recommend for your party or event ”
- Libertyville, IL
- Balloon Twister / Outdoor Party Entertainment
- 25 miles from Woodstock
- Starts at $125
Lisa C. said
“Jon did an excellent job as Santa! All my daycare parents were very impressed. He was in character the whole time and made the children feel comfortable around him. Loved having him as our Santa! It... ”
- McHenry, IL
- Face Painter / Outdoor Party Entertainment
- 9 miles from Woodstock
- $100 – $140 per hour
Katie G. said
“Kema did a wonderful job at our Garden Party event!!! Everyone loved her and her face painting skills were on point!!!! ”
- Mount Prospect, IL
- Balloon Twister / Outdoor Party Entertainment
- 31 miles from Woodstock
- Starts at $160
Dave P. said
“Great balloons and made time for every kid even tho our event went longer than anticipated. ”
- Rockford, IL
- Balloon Twister / Outdoor Party Entertainment
- 33 miles from Woodstock
- Contact for pricing
Gina L. said
“Ms. Twisty Pants was AMAZING at our end of year Girl Scout party. The kids had so much fun with the balloons!! She is super fast and super friendly. HIGHLY RECOMMEND!!! ”
- Wheaton, IL
- Face Painter / Outdoor Party Entertainment
- 36 miles from Woodstock
- Starts at $125 per hour
Amber B. said
“Susanne was absolutely wonderful! She was very attentive to the kids and my daughter was so excited for this birthday surprise! Her attention to detail and artistic talent is unmatched. ”
- Warrenville, IL
- Face Painter / Outdoor Party Entertainment
- 37 miles from Woodstock
- Starts at $180
Laura C. said
“Lazuli Party was so fun and professional! We had a group of 6 year olds at our house and she took her time with each of them to make them feel special while face painting. She even stayed a bit past... ”
- Aurora, IL
- Juggler / Outdoor Party Entertainment
- 39 miles from Woodstock
- $300 – $1,000 per event
Lisa H. said
“This is the second year we hired Andy for our 5th grade event, and he was just as amazing as the first time! His show is charming and funny and keeps the kid's attention the ENTIRE time! He's a pro at... ”
- Crystal Lake, IL
- Face Painter / Outdoor Party Entertainment
- 8 miles from Woodstock
- Contact for pricing
Christina S. said
“She was so easy to work with on scheduling, very responsive. The face painting was beautiful, all of the kids loved it! The balloon twisting was incredible, some very creative pieces. Great addition... ”
- Crystal Lake, IL
- Face Painter / Outdoor Party Entertainment
- 8 miles from Woodstock
- Starts at $150
Henry L. said
“Smiling faces did an excellent job with the kids. She did some beautiful designs. ”
- Crystal Lake, IL
- Face Painter / Outdoor Party Entertainment
- 8 miles from Woodstock
- Contact for pricing
Lori R. said
“Lovex Brooke. Hope to have her join us again! ”
- Marengo, IL
- Face Painter / Outdoor Party Entertainment
- 9 miles from Woodstock
- $130 – $200 per hour
Sam W. said
“Great pre-event communication, arrived on time, and great with the kids. ”
- Lake Geneva, WI
- Mobile DJ / Outdoor Party Entertainment
- 19 miles from Woodstock
- Starts at $495
Avery K. said
“Andrew went above and beyond, making our special day one I will never forget. And of course he sounded great! Highly recommend!! ”
- Lake Zurich, IL
- Food Truck / Outdoor Party Entertainment
- 20 miles from Woodstock
- $800 – $1,000 per event
Briana W. said
“Kurbside Pizza made charcuterie cups for our event. They turned out so cute and our guests loved them. Zero issues, so easy to work with. ”
- Elkhorn, WI
- Face Painter / Outdoor Party Entertainment
- 25 miles from Woodstock
- Starts at $95
Ali R. said
“We booked Prism and Palette Face Painting for our village's big annual 4th of July party and were so thrilled with Shannon's artistry, professionalism, and kind disposition. Children of all ages... ”
- Vernon Hills, IL
- Face Painter / Outdoor Party Entertainment
- 25 miles from Woodstock
- Contact for pricing
Zlatina K. said
“Vera and Nik are amazing! Our daughter's fifth birthday party was a huge success thanks to them! They came on time, worked fast and were great interacting with the kids. Vera's face painting is real... ”
- Palatine, IL
- Fire Performer / Outdoor Party Entertainment
- 25 miles from Woodstock
- Starts at $200
Miri M. said
“An amazing show for our party! Our guests really enjoyed it, especially because it was a surprise! Boo Visual Arts arrived on time and was very communicative throughout the planning process, including... ”
- Palatine, IL
- Fire Performer / Outdoor Party Entertainment
- 25 miles from Woodstock
- Starts at $250
Francine C. said
“Fire Dancer put on a amazing show, she was very professional I will definitely be rebooking again. ”
- Arlington Heights, IL
- Mobile DJ / Outdoor Party Entertainment
- 29 miles from Woodstock
- $200 – $2,000 per event
Jordan T. said
“Schiller Chicago Weddings & Event DJs didn’t just play music—they created an experience. From the ceremony to cocktail hour and then the reception, every song was perfectly chosen to set the right... ”
- Wheeling, IL
- Face Painter / Outdoor Party Entertainment
- 29 miles from Woodstock
- Starts at $150 per hour
Erin E. said
“Sharon did an amazing job at our event! She was quick and did amazing work! ”
- Lake Forest, IL
- Face Painter / Outdoor Party Entertainment
- 31 miles from Woodstock
- Contact for pricing
Melanie D. said
“On time, professional, kids were happy! ”
- Zion, IL
- Face Painter / Outdoor Party Entertainment
- 33 miles from Woodstock
- Contact for pricing
Janine M. said
“What an amazing and talented young lady. The kids loved having their faces painted, as well as well as some of the adults. I'm so happy I book with Party Owl Entertainment. She does amazing work and... ”
- Rockford, IL
- Face Painter / Outdoor Party Entertainment
- 33 miles from Woodstock
- $99 – $200 per event
Dawn J. said
“She did a great job with all the kids. Balloon animals are amazing ”
Kim B.
1 Verified booking- Aurora, IL
- Mobile DJ / Outdoor Party Entertainment
- 39 miles from Woodstock
- Starts at $100
*Currently on a sabbatical due to health issues. Hope to be back better than ever Summer 2026* My musical expertise spans R&B, Hip Hop, Pop/Top 40, House,...
- Crystal Lake, IL
- Face Painter / Outdoor Party Entertainment
- 8 miles from Woodstock
- Contact for pricing
At DaisyBug Facepainting, we bring color, creativity, and unforgettable memories to every event! We specialize in high-quality, hygienic, kid-friendly...
- Carpentersville, IL
- Fire Performer / Outdoor Party Entertainment
- 17 miles from Woodstock
- Contact for pricing
Insured fire spinner and aerialist with over 6 years of experience. Skill sets include: -Fire eating, fire fans, fire hoop and fire dragon staff. - aerial...
- Belvidere, IL
- Face Painter / Outdoor Party Entertainment
- 21 miles from Woodstock
- Starts at $220
Sheila S. said
“Heath entertainment group was professional. They were prompt and did excellent work. I would work with them anytime. Communication prior to the event was incredible. ”
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About booking Outdoor Party Entertainment in Woodstock, IL
Outdoor parties are all about enjoying fun in the sun and creating an atmosphere guests won’t forget. The right entertainment sets the stage, whether that means a live band filling the air with music, a DJ keeping the energy high, or a magician amazing guests with close-up tricks. From stilt walkers and petting zoos to face painters and balloon twisters, professional entertainment brings the spark that transforms any backyard celebration, kids party, or festival into an unforgettable experience.
The cost of hiring outdoor party entertainers in Woodstock, Illinois will vary depending on the type of act, their experience, and the length of the performance. For example, a strolling juggler for a few hours will cost less than a full band or stage show. Contact the local entertainers above to discuss your event details and receive a customized quote.
As you browse Woodstock outdoor party entertainers, check out their profiles to learn about their services, browse photos, and watch promotional videos. Then, read over reviews from past clients to see how they’ve entertained at similar events. When requesting a quote, include key details such as your event location, audience size, performance space, and overall vibe to get the most accurate pricing.
Once you find the entertainer you want to hire, finalize the booking on GigSalad. Our full-service platform makes it easy to book outdoor party entertainment. 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 sit back and enjoy your party!
Outdoor Party Entertainment serving the Woodstock, IL area
These Outdoor Party Entertainment serve the wider Woodstock and Mchenry county area and travel to Bull Valley, Wonder Lake, Lakewood, Union, Crystal Lake, McCullom Lake, Marengo, McHenry, Ringwood, Prairie Grove, Huntley, Alden, Hebron, Lake In The Hills, Harvard, Johnsburg, Oakwood Hills, Cary, Lakemoor, Trout Valley, Algonquin, Chemung, Richmond, Island Lake, Zenda, Spring Grove, Genoa City, Fox River Grove, Volo, and Fox Lake.