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Mr. Lucky and his Orchestra of Tomorrow!

Chicago, IL

$1000-$8000

Travels up to 120 miles

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Overview

Mr. Lucky’s eight-piece band delivers sophisticated vintage cocktail pop, blending jazz, Latin rhythms, and timeless hits from icons like Mancini, Bacharach, and Herb Alpert with swinging horns and lush grooves. The Orchestra transports you to a world where the martinis never run dry and the music never stops orbiting the stars!


Reviews

2 reviews

Small thumbnail image for reviewer Jessica E.

Jessica E.

August 9, 2026

Top Notch Entertainment

Mr. Lucky and his Orchestra of Tomorrow are a group of very talented musicians who are also down-to-Earth. Whether you want them to keep the dance floor hopping as others watch and enjoy the show, or you are looking for them to provide background entertainment for a special event, their personalities and musicianship are sure not to disappoint. I have had the pleasure of working with Kevin (Mr. Lucky) many times over the years and have enjoyed getting to know the rest of his band.

Hired as: Jazz Band


Small thumbnail image for reviewer Ruby S.

Ruby S.

August 7, 2026

Mr Lucky and the Orchestra are delightful!

Mr. Lucky and his Orchestra are delightful to work with! Mr. Lucky was great at communicating and catered to our music requests. The band was lively and got our crowd into the event. I have worked with them several times and will continue to do so!

Hired as: Jazz Band

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Booking information

Price range: $1000-$8000

Languages: English

Gig length: 60 - 240 minutes

Insurance: $500,000 - Liability

Unions: AFM

What to expect

A classic, sophisticated, Vegas-style show with a three-piece horn section, a full rhythm section, and our amazing vocalist, featuring fun tunes of many, many different styles and genres that make you want to dance!

About

Mr. Lucky and his Orchestra of Tomorrow have been playing in the Chicago area for five successful years at venues such as The Drake Hotel, The House of Blues, and our regular monthly gig at the beautiful Roxy Lockport. We are a nine-piece band of experienced and talented professional musicians, and we love the music of Henry Mancini, Burt Bacharach, and Herb Alpert, as well as swing, jazz standards, Latin classics, and great vintage pop songs from the 1950’s through the 1980’s. There’s guaranteed listening pleasure for everyone! Mr. Lucky has also been a proud collaborator with Ruby Spencer for her amazing Live and Lucky: A Ruby Spencer Revue throughout the Chicagoland area!

Additional booking notes

A low-maintenance group with wireless mics for the horns, and a full-sound system of our own for medium-sized venues.

Set list

Fly Me to the Moon
Pink Panther
Spanish Flea
Little Phat Shuffle
Taste of Honey
Cantina Band
Hit the Road, Jack
Rubber Duckie
Work Song
Breezin
Will You Still Love Me Tomorrow
Just a Gigolo
Jersey Bounce
Theme from the Odd Couple
Tequila
Under the Milky Way
At Last
Bei Mir Bist Du Schon
Moon dance
Goody, Goody
Brand New Key
Crazy
Daydream
Love Potion #9
Goldfinger
Crazy Little Thing Called Love
Wade in the Water
I Wanna Be Like You
Valerie
Until You Come Back to Me
I Feel the Earth Move
Clocks
Give Me Just à Little More Time
More Today than Yesterday
Will You Still Love Me Tomorrow
Life on Mars
Hang On, Little Tomato
Give Me One Reason
The Tide Is High
Put a Little Love in Your Heart
Son of a Preacher Man
Chain of Fools
We’ll Meet Again

Influences and inspiration

Henry Mancini, Burt Bacharach, Herb Alpert, Louis Prima, Dusty Springfield, Perez Prado, Lesley Gore, Shirley Bassey, Jacques Brel, Frank Sinatra, the Sherman brothers, Aretha Franklin, Chuck Mangione, Duke Ellington, George Benson, Gordon Goodwin, and Vera Lynn.

Setup requirements

We are fully self-contained group for medium-sized or smaller venues!