Browse 317 swing bands available for hire in Windsor, Ontario, Canada, featuring 760 reviews from real clients with an average rating of 5 out of 5. These professional swing ensembles and jazz groups offer sophisticated entertainment for weddings, parties and corporate events.
From intimate duo performances to full orchestras with brass sections, swing bands provide versatile musical entertainment that works for any celebration. Prices start from $330, with an average of $1,200, with groups offering everything from background dinner music to energetic dance sets that get guests moving.
Of the 317 suppliers listed here, 2 are based within 30 miles of Windsor. The other 315 are willing to travel there.
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Swing bands in Windsor, Ontario, Canada bring the sophisticated sounds of jazz-era music to modern celebrations. These talented musical acts range from intimate duos to impressive full orchestras, each offering the infectious rhythms and smooth harmonies that make swing music ideal for weddings, parties and corporate events.
Professional swing ensembles in your area provide exceptional versatility for any occasion. Most groups smoothly blend classic jazz standards with contemporary material, creating sophisticated atmospheres that appeal to guests across all ages. These talented musicians can adapt their performances from subtle background music during dinner service to energetic dance sets that fill the floor with celebrating guests.
Swing bands in Windsor currently range from $330 to $3,800+, depending on group size, performance duration, and specific requirements. Smaller jazz ensembles and duos typically offer more budget-friendly options, while full orchestras with brass sections and multiple vocalists represent premium entertainment costs. Most clients find excellent value near $1,200, which usually includes professional sound equipment, varied repertoire, and the flexibility to adapt performances throughout different segments of an event.
The average price for Swing Bands available in Windsor, Ontario, Canada is $1,200 (CAD). Above you will also find a budget price and high end price. Contact the supplier you like for an accurate quote.
Based on 61 enquiries for Swing Bands at events in Canada, made through this site in the last two years. Updated 9 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."
The Kensie Jazz and Dance Band
"Perfect Jazz Band!
Secured The Kensie Jazz Band for our 30th Anniversary corporate event. From start to finish they were perfect. Perfect background music while guests are engaging in the social circuit. Perfect background music while being seated and served for dinner. The band can adjust their sound level to your preference. They play a range of music. A live band is a classy touch and adds ambience to any event rather than a standard DJ. It is a completely different vibe. Nice group of people! Good pricing as well. Thank you!"
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!"
Just Us Jazz Band
"Excellent, reliable, and high quality music! John was an absolute delight to work with."
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"
James Anthony's Salute to Sinatra
"James Anthony was amazing when he performed for the United States Congress on Capitol Hill in Washington, D.C. He arrived early to rehearse with a 20 piece group of musicians and was a huge hit. The Congress Members and Senators were asking where I found him and we at the Las Vegas Metro Chamber of Commerce absolutely recommend him. Due to popular demand, we brought him back the next year to perform for the US Senate for their annual gala."