The Brothers Sinatra

Elburn, IL

Contact for rates

Travels up to 120 miles

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Overview

THE HOTTEST NEW GROUP IN SWING! The Brothers Sinatra sing classic songs in the style of Frank Sinatra and similar artists with plenty of laughs along the way in a fun, interactive, and infinitely scalable act for audience members of ALL ages.


Reviews

1 review

Small thumbnail image for reviewer Kim K.

Kim K.

August 18, 2025

Very Entertaining

We hired The Brothers Sinatra for a Music in the Garden event, and they were great. They showed up to the event early and had their set up ready to go in plenty of time. During the event, they were very entertaining. Their singing and banter were enjoyed by our guests, and we received many positive comments that evening. Thank you, Brothers Sinatra, for making our event a success.

Hired as: Oldies Music

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Booking information

Price range: Contact for rates

Languages: English

What to expect

We provide a full service entertainment package including setup and teardown, curated event entertainment (concert, karaoke, Dueling Sinatras, and more), and included social media and print marketing for applicable public events. We always arrive early to guarantee success and pride ourselves in communication leading up to the big day. We always bring vintage props and stage elements to set the ambience and wear suits to emphasize the nostalgia.

About

THE HOTTEST NEW GROUP IN SWING! The Brothers Sinatra sing classic songs in the style of Frank Sinatra and similar artists with plenty of laughs along the way. This fun and interactive show for all ages has been a hit across Chicagoland and beyond. From concerts to karaoke, The Brothers Sinatra are truly unique and always entertaining.

Additional booking notes

We are flexible and scalable to any performance situation!

Team

Jack Sinatra Brother
Tyler Sinatra Brother

Set list

(Love Is) The Tender Trap (1955)
A Foggy Day (Ring-A-Ding-Ding!)
Ain't She Sweet
Ain't That a Kick in the Head
All I Need Is the Girl
All of Me
All or Nothing at All
Almost Like Being in Love
Angel Eyes
Anything Goes
Autumn Leaves
Bad, Bad Leroy Brown
Be Careful, It's My Heart
Bewitched, Bothered and Bewildered
Beyond the Sea
Birth of the Blues
Blue Moon
Blue Skies
Brazil
Bye Bye Blackbird
Candy Man
Cheek to Cheek
Come Dance with Me
Come Fly with Me (live at the Sands)
Come Rain or Come Shine
Day by Day
Days of Wine and Roses
Don't Get Around Much Anymore
Downtown
Drinking Again
Embraceable You
Everybody Loves Somebody (uptempo)
Five Minutes More
Fly Me to the Moon (live)
Fly Me to the Moon (Uptempo)
For Once in My Life
Get Me to the Church on Time
Here's That Rainy Day
How About You?
I Can't Believe That You're in Love with Me
I Get a Kick Out of You
I Get Along Without You Very Well
I Got Rhythm
I Love Paris
I Thought About You
I Wish I Were in Love Again
I Won't Dance
I'm Gonna Live Till I Die
I'm Gonna Sit Right Down and Write Myself a Letter
I've Got the World on a String
I've Got You Under My Skin (live - At Royal Festival Hall)
In the Still of the Night
In the Wee Small Hours of the Morning
Isn't She Lovely?
It Had to Be You
It Happened in Monterey
It Was a Very Good Year
It's Nice to Go Trav'ling
Jeepers Creepers
Just in Time
Just One of Those Things
Just the Way You Are
King of the Road
L.O.V.E.
Learnin' the Blues
Let's Face the Music and Dance
Let's Fall in Love
Love Is Here to Stay
Luck Be a Lady (live)
Makin' Whoopee
Mambo Italiano
Me and My Shadow
Misty
Moon River
Moonlight in Vermont
Mrs Robinson
My Blue Heaven
My Blue Heaven (1960 version)
My Funny Valentine
My Kind of Girl
My Kind of Town (live at The Sands)
My One and Only Love
My Way
Nel blu dipinto di blu
New York, New York
Nice 'n' Easy
Nice Work If You Can Get It
Night and Day
Nothing but the Best
Oh! Look at Me Now
Old Devil Moon
On an Evening in Roma
On the Street Where You Live
On the Sunny Side of the Street
One for My Baby
Orange Colored Sky
Pennies from Heaven
Quiet Nights of Quiet Stars (Corcovado)
Ring-a-Ding Ding!
River, Stay 'Way from My Door
Sentimental Journey
September in the Rain
Singin' in the Rain
Some Enchanted Evening
Someday You'll Want Me to Want You
Somethin' Stupid
Something
Something's Gotta Give
Somewhere Over the Rainbow
South of the Border
Strangers in the Night
Summer Wind (Solo)
Sway (Quien Sera)
Sweet Caroline
Swinging on a Star
Tangerine
That Old Black Magic
That's Amore
That's Life
The Best Is yet to Come
The Coffee Song
The Girl from Ipanema
The Good Life
The Impossible Dream (The Quest)
The Lady Is a Tramp
The Shadow of Your Smile (live)
The Way You Look Tonight
The World We Knew (Over and Over)
They Can't Take That Away from Me
Too Close for Comfort
Until the Real Thing Comes Along
Wave
We'll Meet Again
What a Wonderful World
When You're Smiling (The Whole World Smiles with You)
Witchcraft
Yes Sir, That's My Baby
Yesterday
You and the Night and the Music
You Are the Sunshine of My Life
You Make Me Feel So Young
You Make Me Feel So Young (live at the Sands)
You'd Be So Nice to Come Home to
You're Nobody till Somebody Loves You
Young at Heart
Zing! Went the Strings of My Heart

Influences and inspiration

Frank Sinatra, Dean Martin, Sammy Davis Jr., The Rat Pack, Bobby Darin, Louis Armstrong, Ella Fitzgerald, Mel Torme, Bing Crosby, Michael Buble, Harry Connick Jr., Nat King Cole, Count Basie, Duke Ellington

Setup requirements

Access to power

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