Browse 126 professional big bands available for hire in Windsor, Ontario, Canada. These swing orchestras and jazz ensembles have earned 172 reviews from real clients with an average 5 out of 5 rating, bringing authentic swing era sound to weddings, corporate events and special celebrations.
Of the 126 suppliers listed here, one is based within 30 miles of Windsor. The other 125 are willing to travel there.
Based more than 30 miles from Windsor, nearest first
No reviews yet
Book from €250 (EUR)
Add to favouritesNo reviews yet
Book from POA
Add to favouritesNo reviews yet
Book from €1000 (EUR)
Add to favourites(1) Replies in ~4 hrs
Book from POA
Add to favouritesNo reviews yet
Book from €1600 (EUR)
Add to favouritesNo reviews yet
Book from €3800 (EUR)
Add to favourites(2)
Book from €440 (EUR)
Add to favouritesTell us about your event and we'll suggest suppliers, or talk to our team.
The average price for Big Bands available in Windsor, Ontario, Canada is $1,150 (CAD). Big band hire in Windsor currently ranges from $280 to $6,000+, with most professional swing orchestras averaging $1,150 for standard event bookings. Local pricing reflects ensemble size, performance duration and travel requirements within your area. Full orchestras with established reputations command premium rates, while emerging jazz ensembles offer excellent value for budget-conscious event planners seeking authentic big band sound. Contact the supplier you like for an accurate quote.
Based on 710 enquiries for Big Bands at events in every location, made through this site in the last two years. Updated 16 October 2026.
Rick Holland's Uptown Society Orchestra
"All Music Review
Thom Jurek
The title of this set is an apt one. While much of the music presented by the Rick Holland-Evan Dobbins Little Big Band, it hearkens back -- in terms of its sophistication, confidence and outright jazz literacy, not nostalgically -- to an era when progressive jazz, and big bands (this one numbering 10 pieces) flourished on the scene. This is one sophisticated outfit. Featuring the arrangement and compositional skills of Brent Wallarab, Jim Martin, Bill Dobbins and Kerry Strayer, this band struts out the tradition and make some joyous, complex, and elegant music that reflects its own unique identity. The résumés of all these players are impressive and reflected in the confidence of the date. It opens with "SUNY-Triangle," a Martin composition that works its artful sleight-of-hand over Antonio Carlos Jobim's "Triste." Martin uses the rhythmically complex samba and drapes some tough, knotty twists and turns over it. The intro is a beautiful and raucous wake-up call, while the head of the tune, with its staggered entrances and exits -- including some fine soloing by John Viavattine on tenor and John Nyerges on piano -- give this tune a unique identity. "Creature Comfort" is a beautiful mid-tempo ballad by Wallarab with edgeless yet multi-dimensional dissonances written into its harmonics. It swings beautifully and includes a fine, punchy solo by tenorman Glenn Cashman. Besides the originals, there are some fine readings here as well. There's Wallarab's arrangement of Duke Ellington's "Black and Tan Fantasy" that's a thoroughly modern exercise losing none of Ellington's humor or rhythmic complexity. Likewise, Gerry Mulligan's haunting, wee-hours, "Night Lights," is given expert treatment here by Strayer, and Dean Keller's baritone saxophone playing combines Mulligan's sense of lyric and Ben Webster's sense of time. In Time's Shadow reveals that innovation need not sacrifice accessibility or swing. It is convincing evidence that the big band form is alive, well and full of surprises."
Swing Shift Big Band/Wedding Band
"Thank YOU and the band so much - I'm only sorry we cut into your playing time (speeches and photos)! Everyone absolutely loved the band and was blown away by your sets- we'll hope to catch you and the full Swing Shift band at the Rex sometime in the future and buy you a drink!"
The Rick Levine Band
"Fantastic Band! Rick is easy to work, dance floor was full all night long. Guests are still talking about how the Rick Levine Band helped make my event a success! Thanks."
The Ron Smolen Big Band / Orchestra
"Wedding October 14 2023 - University Club - Chicago, IL
Hi Ron,
I've been meaning to shoot you an email.
Thank you guys so much, we had such a wonderful time and were so happy and impressed with the music. With everything going on, there were 2 things about the wedding that made it stand out: the food and the band. Our guests loved the music and it was everything that we could have ever wanted and more.
I really meant what I said about how cool it is that you all play this music and hopefully more people my age appreciate the work that you all do. Please let me know if there is anything I can do for you. We visit Chicago pretty often so we'll keep tabs on when you play and will come say hello sometime soon.
Hope you have a happy Thanksgiving!
-Ryan & Angela"
JBaxterMusic Consortium LLC
"All we can say is Wow! Jay and his crew were amaaaaaazing! Truly made the night so memorable and fun. We couldn't be happier. From the minute they got to our house until they packed up their last instrument, they were nothing but professional, polite, respectful and friendly. And let's talk about how talented and entertaining they were! Even our neighbors said that they sat in their driveway and enjoyed the sounds of the evening. They truly ""brought the house down"" and we couldn't be more grateful and appreciative. We thanked Jay, and Rob's in touch w him about Venmo-ing, what we hope is a generous tip for him and his band. Monica, you too have been nothing but so helpful and gracious. It takes a village and we are so grateful for our fantastic village of vendors such as you and Jay. Thanks again for everything!!
Tracie T."
Sinatra & Friends Entertainer
"Our top performer. Friendly, accommodating has audio equipment to handle any type of performance."