MERRY CHRISTMAS BABY

December 10 (Two Shows!)

Dizzy’s Club

Celebrate the season with Chicago’s own Tammy McCann, as the powerhouse vocalist and bandleader returns to Dizzy’s Club for a soulful, hard-swinging holiday set. Known for her rich storytelling and unforgettable voice, McCann brings fresh spirit to seasonal favorites in a performance full of warmth, joy, and timeless swing. It’s a festive night that welcomes every listener.

WINTER IN MANHATTAN: Songs of Snowfall, City Lights, and Christmas Dreams

December 11 @ 7:00PM

St. John’s in The Village

Celebrate the magic of the holidays with Shana Farr, special guest Steve Ross, and Music Director Jon Weber in Winter in Manhattan. From the rush of holiday shoppers and the glow of Fifth Avenue windows to the quiet peace of a snowy night, this evening will remind us what this time of year is truly about — love, laughter, gratitude, and the joy of being together. Featuring favorites like "It’s the Most Wonderful Time of the Year", "White Christmas", "Winter in Manhattan", "You're a Mean One Mr. Grinch", "It's Almost Christmas Eve", "Believe", "O Holy Night", and more!

HOLIDAY SPECIAL

December 12 @ 7:00PM

The Green Room 42

Celebrate the season with Broadway’s favorite duo—and real-life couple—Nicolas Dromard & Desiree Davar in a dazzling evening of music, dance, and holiday cheer. With Broadway credits including Wicked, Jersey Boys, Mary Poppins, and West Side Story, Nic & Desi light up the stage with their signature blend of talent, charm, and undeniable chemistry. Nic & Desi’s Holiday Special is a festive throwback to the golden era of live TV variety shows—think Judy Garland, Bing Crosby, and a nod to White Christmas, the show where their own love story began. Part concert, part classic holiday special, this retro-inspired evening is packed with show-stopping choreography, nostalgic tunes, and a few sparkling surprises.

GLITTER AND BE GAY!

December 13 @ 9:30PM

Laurie Beechman Theatre

Born to glitter and be gay, American Idol Finalist, Ava Nicole Frances is thrilled to celebrate the holidays in her unique way. Sure, there will be glitz and glam and gayety but also the heart and soul of a young woman in love with the season and the joy and longing it brings. You will hear holidays favorites, songs of the season, iconic pop and Songbook selections –everything from Adele to Sabrina Carpenter and Leonard Berstein to Cole Porter. Add in a little Judy, Liza and Barbra and you have a warm intoxicating holiday cocktail, perfect on a winter’s eve.

LIVE AT BIRDLAND

December 13, 20 @ 5:30PM

Birdland Jaz Club

"Ms. Stravelli’s emotional intelligence coincides with a phenomenal voice that she wielded with an easygoing confidence and impeccable taste."  - The New York Times. Gabrielle Stravelli combines a tremendous swing feel with a gift for lyric interpretation, leading to a richly varied career defined by highly individual choices and a genuine connection with audiences. In the last year Gabrielle made her Carnegie Hall debut with the New York Pops Orchestra and released her fifth album, "Beautiful Moons Ago." 

IT'S CHRISTMAS TIME IN THE CITY

December 9 & 10 @ 7:00PM

Laurie Beechman Theatre

The dazzling Broadway Diva Stephanie Pope and the Clown Prince of Cabaret join forces to welcome in the holidays with seasonal songs from Broadway and film, as well as metro-centric standards in sparkling, new arrangements. Stephanie Pope is a singer, dancer and actress and a musical theater veteran with a career spanning over 35 years. Mark Nadler is an internationally acclaimed singer, pianist, tap-dancer, and comedian

SNOW BIZNESS

December 13, 19 & 27 @ 7:00PM

Laurie Beechman Theatre

Do you hear what I hear?  17 years ago, Christine Pedi, created holiday magic on The Beechman stage...after a lawsuit by St. Nicholas (no joke), a title change, and adopting the dog of her dreams, she's coming back home to The Beechman and bringing her annual holiday show with her! All you want for Christmas is  Barbra Streisand, Patti Lupone, Liza, Julie Andrews, Carol Channing and all you favorite Divas stuffed into one big musical Christmas stocking?

FRIVOLITY HOUR

December 15 @ 7:00PM

Birdland Jazz Club

Come see why Broadway World named The Bryce Edwards Frivolity Hour one of the ”not to be missed,” best cabaret shows of 2024, alongside entertainment royalty such as Patti LuPone, Bernadette Peters, and Marilyn Maye (to name a few). Edwards is a unique vocalist who takes equal cues from the crooners and soft singers of the late 1920s and early 1930s and from the bombastic voices of the earlier acoustic phonograph era, as well as an instrumentalist who plays banjo, ukulele, tenor guitar, and mandolin in the “modernistic” jazz idiom.

LET ME CARRY YOU THIS CHRISTMAS ALBUM RELEASE

December 16 & 17 @ 7:00PM

54 Below

Darius shares his love of the holidays, cherished family memories, and expanding his musical palette through timeless classics like “We Need A Little Christmas,” “Silent Night,” “Have Yourself A Merry Little Christmas,” as well as the Steve Allen penned “Cool Yule” (introduced by Louis Armstrong) and newer songs destined to become classics such as Mervyn Warren’s “Who Would Imagine A King” (from The Preacher’s Wife), Annie Lennox’s “Cold” and the title song “Let Me Carry You This Christmas” written for Darius by Tom Mizer and Curtis Moore.

A NAT KING COLE CHRISTMAS

December 19 @ 7:00PM

Pangea Restaurant and Bar

Celebrate the season with the incomparable Allan Harris as he brings his velvet-smooth voice and soulful swing to A Nat King Cole Christmas. In this intimate holiday concert, Harris channels the elegance, warmth, and timeless charm of Nat King Cole—performing beloved classics with his own signature style and irresistible charisma. From “The Christmas Song” to other seasonal favorites, it’s a heart-lifting evening filled with rich vocals, masterful guitar, and the kind of glow only great jazz can bring.

CHRISTMAS! CHRISTMAS! CHRISTMAS!

December 19-21 @ 7:00PM

The Green Room 42

It’s more than a holiday concert! With Karen’s unique interpretations of holiday classics, old and new, your holidays will never be the same! Sassy, brassy, and tinged with confessional monologs, this show includes a heartfelt “I’ll Be Home for Christmas”, and her 2 new singles:  a slinky arrangement of “Santa Claus Is Coming To Town”, a new standard “It’ll Be Christmas Before You Know It”. And many, many more surprises!  Karen’s Christmas show will be your new holiday essential!

LIVE AND IN PERSON!

December 20 @ 7:00PM

Don’t Tell Mama

Don’t miss MAC Award–winning performer Justin Dylan Nastro as he takes the stage for a high-voltage, one-night-only evening of music, storytelling, and irresistible charm. With his trademark versatility and powerhouse vocals, Justin brings a vibrant mix of songs to life—backed by the incomparable Tracy Stark as Musical Director and under the sharp, dynamic direction of Lennie Watts. It’s an unforgettable night that showcases Justin at his boldest, brightest, and most personal.

YOU CAN'T MAKE OLD FRIENDS (HOLIDAY SHOW)

December 21 @ 4:00PM

Don't Tell Mama

Celebrate the season with longtime musical partners Marissa Mulder and Bill Zeffiro as they bring their trademark warmth, wit, and award-winning artistry to this festive holiday edition of You Can’t Make Old Friends. Blending heartfelt storytelling with beautifully crafted arrangements, this beloved duo offers a charming, intimate afternoon of songs that sparkle with nostalgia, joy, and the magic of true friendship. It’s the perfect way to usher in the holidays—cabaret-style.

SONGBOOK SUNDAYS: GERSHWIN

December 21 (Two Shows!)

Dizzy’s Club

Celebrate the timeless music of George and Ira Gershwin with Songbook Sundays: Gershwin, part of the beloved bi-monthly series curated and hosted by Deborah Grace Winer. Pianist and music director Ted Rosenthal leads an all-star ensemble featuring Linda Purl, Nicolas King, and Imani Rousselle in fresh, swinging takes on the Gershwins’ greatest hits. It’s a joyful afternoon of classic melodies, heartfelt vocals, and vibrant jazz celebrating one of America’s most enduring musical legacies.

SIDNEY MYER RIDES AGAIN!

December 21, 23, 27, 29, 31 @ 7:00PM

Pangea Restaurant and Bar

Cabaret icon Sidney Myer returns to the stage with Sidney Myer Rides Again!—an irresistible evening of comedy, song, and the singular storytelling that has made him a beloved legend of the nightclub world. Backed by the brilliant Tracy Stark, Skip Ward, and David Silliman, Myer delivers a show overflowing with mischief, heart, and the kind of magic that only he can conjure.

A SWINGING BIRDLAND CHRISTMAS

December 21-22 (Four Shows!)

Birdland Jazz Club

Inspired by the great television variety specials of yesteryear, the show brings together Klea Blackhurst, Jim Caruso, and Billy Stritch for an evening of swinging seasonal cheer. With dazzling arrangements of classics like “The Christmas Waltz,” Kay Thompson’s “Holiday Season,” “I’ve Got My Love to Keep Me Warm,” “Snow,” and “It Happened in Sun Valley,” the trio infuses timeless favorites with wit, warmth, and plenty of swing.

JINGLES AND JAZZ

December 22 @ 7:00PM

The Green Room 42

Jingles and Jazz is Rosemary Loar's latest musical creation featuring her world class trio, Frank Ponzio/piano/music direction, Tom Hubbard/Double Bass, Vito Lesczak/Drums, and directed by Barry Kleinbort. You will hear some your some of your favorite holiday songs with a very Rosemary twist.  She will some original songs penned and per usual true stories from her life. This time about her childhood Christmas growing up in a large family where getting a tree that fists in the living room seems to be the impossible dream.

‘TIS THE SEASON

December 27 @ 7:00PM

The Green Room 42

2023 Bistro Award RecipientTim Connell will present his new holiday-themed show, ‘TIS THE SEASON, with his inimitable aesthetic of story and song woven together, to awaken the holiday spirit. In addition to cherished holiday classics, the evening will include funny, irreverent, and not so classic holiday selections, as well as reflections and observations that speak to the meaning of this extraordinary time of year. A Perfect way to kick off “the season”! Musical Director: James Followell, Director: Mark Chmiel, Drums: Ray Marchica, Bass: Sean Conly

LET THE MUSIC PLAY TOGETHER AGAIN!

December 28 @ 7:00PM

The Green Room 42

Heather and Allan will reunite on the cabaret stage of the Green Room to reimagine songs from the Broadway Shows “Hair” and “Jesus Christ Superstar” in which they appeared together. They’ll also sing selections from shows in which they performed individually along with a special treat - songs from the Robert Altman film “A Perfect Couple” in which Heather starred and Allan co-wrote.

A TINY MATCH

December 29 @ 7:00PM

Birdland Jazz Club

Singer Maude Maggart will make her annual return to Birdland with a new show, entitled "A Tiny Match." The one-night-only show will begin at 7pm. Through the songs of Cole Porter, Ivor Novello, Jerome Kern, to modern songwriters, Maude will weave the past and the present to take us on a musical journey of what it means to be living in a never-ending changing world. 

NEW YEAR’S EVE

December 31 @ 7:00PM

54 Below

The legendary Charles Busch returns to 54 Below to ring in the New Year with his unique mix of stories and songs. Accompanied by his musical director, Jono Mainelli, and a band of top musicians, Charles will perform an eclectic repertoire which includes the best of Jerome Kern, Stephen Sondheim, the Andrews Sisters, and seventies disco.

NEW YEAR'S EXTRAVAGANZA

December 31 - January 4

Birdland Jazz Club

Celebrate the New Year in style with legendary cabaret icon Marilyn Maye as she returns for a sparkling multi-date engagement filled with music, magic, and Marilyn’s unmistakable joie de vivre. Joined by her superb band, Marilyn delivers an irresistible blend of swinging standards, heartfelt ballads, and the kind of show-stopping moments only she can conjure. Start your year on the highest note—experience Marilyn Maye at her radiant best.