Congratulations on your Upcoming Wedding or Special Event!


Thank you for visiting Chill Will! founded in Boston Massachusetts providing finest class of DJ’S, and quickly becoming Southwest Florida’s First choice. My name is Bill/ Pelosi/DJ, Entertainment Director, Owner and founder of the company in 1980. After serving Boston Massachusetts for 25 years I have relocated to Southwest, Florida in the fall of 2006 and am quickly re-establishing myself. We have one simple goal, to provide you with the best quality DJ Entertainment Services Boston, New England and Ft Myers, Southwest Florida has to offer. This is your special day and event. We want you to be sure you have made the right decision with your professional wedding, event DJ entertainment choice. We appreciate your time, and consideration. Please continue viewing our site regarding information provided about myself, my staff of professional DJS and our services we offer.

We Offer Uplighting and Photo Booth for Weddings That Will Enhance Your Wedding or Event


Uplighting is the art of painting with light to create a truly magical background for the most beautiful and well planned days of your lives together as a couple. Uplighting brings your wedding to life, dresses, your flowers and the room will all work together to create an inviting entertaining space. The secret lies in the type of lighting, where to place the lighting, and using it to enhance and boost the already beautiful aspects of your wedding venue. Photo Booths are a blast, imagine you, your family and friends letting loose with props and hats and jumping in the photo booth that can holed up to eight people…..Smile

Cypress Ranch Wedding Punta Gorda Florida

Cypress Ranch Wedding Punta Gorda Florida

Charlotte Harbor Event Center Wedding Punta Gorda Florida

Charlotte Harbor Event Center Wedding Punta Gorda Florida

White Orchard Oasis Ft. Wedding   Myers Florida

Heron Creek North Port FL

Photo Booths for Weddings & Events

Photo Booths for Weddings & Events


Experience Matters


Bill aka Chillwill and his wife

Bill Pelosi/DJ & Director of Music & Carol M Pelosi

  • Florida Licence: C12000113900 and Insured
  • Professional DJ with 25 years of experience (Dressed In Tuxedo)
  • Professional DJ Equipment (Backup Same Quality) Cordless Microphone
  • Complete Music Collection (Includes Ceremonial & Cocktail)
  • Create “Your” Online Music Play List With Over 80,000 Songs!
  • Complete On-Line Event Forms To Help Plan Your Wedding Day / Special Event!
  • Unlimited Email Communication To Your DJ
  • Consultations To Finalize Your Wedding Details
  • We work professionally "Behind The Scenes" With Your Other Wedding Vendors.
  • Very Approachable For Taking Requests,
  • If A Bride Has A "Do Not Play List" We Simple Do Not Bring That Song!

Like to schedule a no obligation consultation 239.573.2695, Cell 617.943.9092, 800.974.1800 or e-mail us. with any questions.

Choosing Chill Will DJ was one of the best choices we made for our wedding day! From day one they were flexible and ready to help us in any way. Everyone was dancing from the beginning to the end, and everyone said what a great DJ! Great music for all ages! Thank you!

A Special Thank You To Our Troops


Thank You Veterans

American Flag

“At home and abroad, military men and women are showing purpose and dedication in defending American ideas. They are performing in our country’s best traditions under circumstances both difficult and complex. Thanks to their determined spirit of patriotism and professionalism, our country has a powerful and unified defense team, employing its forces in the constant quest for peace and freedom.”
» The Honorable Melvin Laird

Any currently active duty and veterans will receive a $100.00 discount
on any wedding package only.

Wedding Wire Bride's Gold Choice Award 2009, 2010, 2012 and 2013,2014, 2015, 2016, 2017

wedding wire award 2009 wedding wire award 2010 wedding wire award 2011 wedding wire award 2012 wedding wire award 2013 wedding wire award 2014 wedding wire award 2015 wedding wire award 2016 wedding wire award 2017 wedding wire award 2018

The Wedding Wire Bride's Choice Awards ™ recognizes the top local wedding professionals from the Wedding Wire Network that demonstrate excellence in quality, service.