Bill Pelosi DJ/MC & Director of Music

We make planning your wedding fun offering online planning tools to create a custom play list, online wedding planner, time line from our online music library of 80,000 plus titles from the 50's today hits

We are fully licensed and insured

"From Your First Dance To Your Last"

We have You Covered

DJ Bill Pelosi

I’m personally open for bookings for the Greater Boston area for the months of June, July ,August and September.

Chill-Will DJ’S providing world class DJ’S for Greater Boston, and growing in Southwest Florida’s. My name is Bill/DJ, Entertainment Director, owner and founder of the company in 1980. After serving the Greater Boston Massachusetts area for 25 years I have relocated to Southwest, Florida in the fall of 2006 and I have established myself in Southwest Florida. We have one simple goal, to provide you with the best quality DJ Entertainment services Greater Boston, New England and Southwest Florida has to offer. This is your special day and event. We want you to be absolutely sure you have made the right decision for your event with your DJ entertainment choice. We appreciate your time, and consideration. Please continue viewing our site regarding information provided about myself, my staff and our services.

Check out our reviews

Boston , wedding, djs

DJ Ron is a seasoned professional DJ working with Chill-Will DJS for over 25 years

Ron brings a passion and with the flow to any crowd. His music knowledge will have your dance floor pumping with energy. Commitment to the Event that shows in everything he does. Ron’s has a natural ability to adapt and go with the flow. Ron fit’s into the Chill-Will DJS Boston team quite well as he shares our belief in approaching each wedding and event with an open mind and mixing up the music to suit the audience at hand.



Wedding Packages

"From Your First Dance to Your Last We have you Covered"

Wedding Package 1

$1,195

Includes 5 Hours of playing Total time

Wedding Package 2

$1,295

Includes 6 Hours of playing Total time

Reception Only
4 Hours

$895

Overtime if Requested $125

Reception Only
5 Hours

$995

Overtime if Requested

No Obligation Consultation to meet. Florida Licensed & Liability Insured

Wedding Package 1: Cost $1.195.00 5 hours.

  • State of the art sounds systems (2) which includes ceremony and 4 Hour Reception
  • (Ceremony must be within Venue property)
  • Wireless Microphone for Ceremony
  • 4 lighting fixtures for your dance floor.
  • Online Tools: Build your custom Playlist, Planner & Timeline
  • Arrive 2 hour setup time prior to start ceremony
  • Professional DJ/MC
  • 5 Hours of playing Total time.
  • Unlimited Email/Phone Communication plan your wedding 24/7 with over 70,000 Songs
  • Final consultation with your DJ prior to your wedding to finalize all your details.
  • Stand Alone Speaker system for a Cocktail Hour if needed $100.00
  • Breakdown and travel up to 40 miles of FT Myers (Beyond Additional)
  • Upgrade with sub woofers $100.00 (suggested with 150 or more guests)

Wedding Package 2: Cost $1,295.00 For 6 Hours

  • Premier sound systems (2) which includes ceremony and 5 Hour Reception
  • (Ceremony must be within Venue Property)
  • Wireless Microphone for Ceremony
  • Cocktail Stand alone speaker system
  • DJ Pre Preparation
  • 2 Lighting Fixtures for your dance floor.
  • Online Tools: Build your custom Playlist, Wedding Planner & Timeline
  • Arrive 2 hour setup time prior to start of ceremony
  • Professional DJ/MC
  • 6 Hours of playing Time Total
  • Unlimited Email/Phone Communication plan your wedding 24/7 with over 80,000 Songs
  • Final consultation with your DJ prior to your wedding to finalize all you details.
  • Breakdown and travel up to 40 miles of FT Myers (Beyond Additional)
  • Upgrade with sub woofers $100.00 (Suggested 150 guests or more)


  • State of the art sounds systems (2) which includes ceremony and 4 Hour Reception
  • (Ceremony must be within Venue property)
  • Wireless Microphone for Ceremony
  • 4 lighting fixtures for your dance floor.
  • Online Tools: Build your custom Playlist, Planner & Timeline
  • Arrive 2 hour setup time prior to start ceremony
  • Professional DJ/MC
  • 5 Hours of playing Total time.
  • Unlimited Email/Phone Communication plan your wedding 24/7 with over 70,000 Songs
  • Final consultation with your DJ prior to your wedding to finalize all your details.
  • Stand Alone Speaker system for a Cocktail Hour if needed $100.00
  • Breakdown and travel up to 40 miles of FT Myers (Beyond Additional)
  • Upgrade with sub woofers $100.00 (suggested with 150 or more guests)
  • State of the art sounds systems (2) which includes ceremony and 4 Hour Reception
  • (Ceremony must be within Venue property)
  • Wireless Microphone for Ceremony
  • 4 lighting fixtures for your dance floor.
  • Online Tools: Build your custom Playlist, Planner & Timeline
  • Arrive 2 hour setup time prior to start ceremony
  • Professional DJ/MC
  • 5 Hours of playing Total time.
  • Unlimited Email/Phone Communication plan your wedding 24/7 with over 70,000 Songs
  • Final consultation with your DJ prior to your wedding to finalize all your details.
  • Stand Alone Speaker system for a Cocktail Hour if needed $100.00
  • Breakdown and travel up to 40 miles of FT Myers (Beyond Additional)
  • Upgrade with sub woofers $100.00 (suggested with 150 or more guests)
  • State of the art sounds systems (2) which includes ceremony and 4 Hour Reception
  • (Ceremony must be within Venue property)
  • Wireless Microphone for Ceremony
  • 4 lighting fixtures for your dance floor.
  • Online Tools: Build your custom Playlist, Planner & Timeline
  • Arrive 2 hour setup time prior to start ceremony
  • Professional DJ/MC
  • 5 Hours of playing Total time.
  • Unlimited Email/Phone Communication plan your wedding 24/7 with over 70,000 Songs
  • Final consultation with your DJ prior to your wedding to finalize all your details.
  • Stand Alone Speaker system for a Cocktail Hour if needed $100.00
  • Breakdown and travel up to 40 miles of FT Myers (Beyond Additional)
  • Upgrade with sub woofers $100.00 (suggested with 150 or more guests)

Reception Only Package 3

4 Hours $895.00 & 5 Hours $995.00

Reception Only Package Included:

  • DJ Pre Pre Preparation
  • 4 Lighting fixtures for Dance Floor
  • 1.5 hour setup time prior to start time
  • Professional Seasoned DJ/MC
  • Online Tools: Build your custom Play List,
  • Wedding Planner and Time Line.
  • Unlimited Email/Phone Communication plan your wedding 24/7 with over 80,000 Songs
  • Final consultation with your DJ prior to your wedding to finalize all your details.
  • Travel & Breakdown and travel up to 40 miles of FT Myers (Beyond Additional)Ceremony may be included in this package if a second system is not needed
  • Upgrade to sub woofers. Suggested with150 guest or more
  • Overtime if Requested $125.00
  • We hold the Wedding Wire "Brides Choice Awards"



  • State of the art sounds systems (2) which includes ceremony and 4 Hour Reception
  • (Ceremony must be within Venue property)
  • Wireless Microphone for Ceremony
  • 4 lighting fixtures for your dance floor.
  • Online Tools: Build your custom Playlist, Planner & Timeline
  • Arrive 2 hour setup time prior to start ceremony
  • Professional DJ/MC
  • 5 Hours of playing Total time.
  • Unlimited Email/Phone Communication plan your wedding 24/7 with over 70,000 Songs
  • Final consultation with your DJ prior to your wedding to finalize all your details.
  • Stand Alone Speaker system for a Cocktail Hour if needed $100.00
  • Breakdown and travel up to 40 miles of FT Myers (Beyond Additional)
  • Upgrade with sub woofers $100.00 (suggested with 150 or more guests)
  • State of the art sounds systems (2) which includes ceremony and 4 Hour Reception
  • (Ceremony must be within Venue property)
  • Wireless Microphone for Ceremony
  • 4 lighting fixtures for your dance floor.
  • Online Tools: Build your custom Playlist, Planner & Timeline
  • Arrive 2 hour setup time prior to start ceremony
  • Professional DJ/MC
  • 5 Hours of playing Total time.
  • Unlimited Email/Phone Communication plan your wedding 24/7 with over 70,000 Songs
  • Final consultation with your DJ prior to your wedding to finalize all your details.
  • Stand Alone Speaker system for a Cocktail Hour if needed $100.00
  • Breakdown and travel up to 40 miles of FT Myers (Beyond Additional)
  • Upgrade with sub woofers $100.00 (suggested with 150 or more guests)

Additional Services:

Proms, School Dances. We are a Florida Public School Contractor.

Led Wireless Uplights.

Prices based on a 40 mile radius of FT Myers or Boston and does not include any ferry or Island Transfers

(beyond additional charge for travel)

Special Events

Proms and Homecomings

Chill-Will DJ's Service is Licensed, Insured and a Florida State School Contractor

uplighting, wedding reception, ft myers, fl
dmx lighting, dj booth, ft myers, naples, cape coral

Chill-Will DJ Service is one of the best Professional DJ companies in the business because of our experience, dedication to customer satisfaction. We understand that this is your special day and will work to ensure all of your needs are met. Chill-Will DJ'S works with your other vendors, playlist, take requests, handle your formalities, MC, follow your playlist, read your guests, and keep your wedding upbeat and timeline flowing on track.

We Look forward to earning your business and exceeding your expectations.

We offers the following services:

• No Obligation Consultation to meet.

• Florida Licensed & Liability Insurance

If you would like to schedule an appointment please call: 239.573.2695 - 617.943.9092 or

e-mail [email protected] with any questions you might have. This is for within a 40 mile radius of Boston. Additional charge depending on location of venue. Does not include any ferry transfers.

Additional Lighting Packages Available

Professional Wedding Digital Videographers serving greater Boston Massachusetts/New England for over 25 years..

Capture your most precious moments. Kibby Productions provides you with wedding memories that

will live in your hearts forever. A wedding DVD of your wedding day is something you’ll treasure

for years to come. Call for an appointment; 617.846.3432

Visit Kibby Productions

Chill-Will DJ Service Serving Greater Boston

Chill-Will DJ Service Established 1980

Proudly Serving Greater Boston

Massachusetts, Greater Boston, North, Shores, Cape Cod,

Islands, Southern New Hampshire, NH

Contact Us

Bill “Chilly” Pelosi

Phone239.573.2695,

Cell617.943.9092


About Chillwill DJs

Bill Pelosi/DJ Director of Music

2119 Northeast 19th Place

Cape Coral 33909

chillwilldjs@aol.com

Established in 1980

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