Lookingglass Theatre Company

Chicago’s Tony-Award winning Lookingglass Theatre Company, is proud to announce multi-award winner Anthony Rapp in the world premiere of a seasonal and intimate cabaret, Anthony Rapp: Home for the Holidays, December 17 - 20, at historic Water Tower Water Works, 163 E. Pearson St. at Michigan Ave. 
There’s nowhere star of Broadway stage and screen, Anthony Rapp (Rent, You’re a Good Man Charlie Brown, “Star Trek: Discovery”) would rather be than home, in Chicago, for the Holidays this December. 
All are invited to experience an intimate holiday cabaret at Lookingglass Theatre accompanied by Rick Bertone and joined by some of Chicago’s favorite voices, this is a unique night that will leave audiences feeling merry and bright.
 
Anthony Rapp is thrilled to return to live and work in the city of his birth. Chicago is also where he earned his Equity card 45 years ago, when he was nine years old. He has since appeared on Broadway, Off-Broadway, in National Tours, at Regional Theatres and in films and on television. But his proudest work these days is as the father, with his husband Ken, of their two sons, Rai (aged 3) and Keony (aged 2). 
 The performance schedule is Wednesday, Dec. 17 through Friday. Dec. 19 at 7 p.m. and Saturday, Dec. 20 at 2 p.m. and 7 p.m. Tickets are now on sale for $55 - $340 with additional information available at <a href="https://lookingglasstheatre.org/" rel="nofollow" target="_blank">LookingglassTheatre.org. </a>

Local Event: Lookingglass Theatre Company Presents “Anthony Rapp: Home for the Holidays,” Dec. 17 - 20

Cook County

Chicago

Illinois

Lookingglass Theatre Company Presents “Anthony...

Chicago’s Tony-Award winning Lookingglass Theatre Company, is proud to announce multi-award winner Anthony Rapp in the world...

Lookingglass Theatre Company Presents “Anthony Rapp: Home for the Holidays,” Dec. 17 - 20

North Shore Center for the Performing Arts in Skokie

Music Theater Works is proud to announce the cast and creative team for the fourth and final production of its 2025 season, Annie, in the George Van Dusen Theatre, at the North Shore Center for the Performing Arts in Skokie, 9501 Skokie Blvd, Skokie, December 18 - January 4, 2026. Annie, with music by Charles Strouse, lyrics by Martin Charnin, and book by Thomas Meehan, is directed by Producing Artistic Director Kyle A. Dougan, choreographed by Mollyanne Nunn and music directed by Michael McBride. 
 
For more than a century, audiences around the world have been inspired by the story of Annie, the spunky, red-headed orphan whose unshakable optimism transforms everyone she meets, including billionaire Oliver “Daddy” Warbucks. Winner of seven Tony Awards, including Best Musical, Annie shines with some of the most beloved songs in musical theatre history, such as “Tomorrow,” “NYC” and “You’re Never Fully Dressed Without a Smile.” In this fresh reimagining, a modern city finds new light through Annie’s hope and determination, reminding us that love, generosity and courage can change even the darkest of days … and that home is where the heart dares to hope. 
 
The cast of Annie includes, in alphabetical order, is Catharina Araujo (she/her, Tessie); Diana Marilyn Alvarez (she/they, ensemble/U/S); Eric Amundson (he/him, ensemble/Sound Effects Man/others); Audrey Bucholz (she/her, Molly); Kristin Brintnall (she/her, ensemble/Bonnie/others, U/S Lily St. Regis); Jenny Couch (she/her, ensemble/Ronnie/others/U/S Grace Farrell); Eric Desnoyers (he/him, ensemble/Henry Morgenthau/others/U/S); Molly Dibble (she/her, Duffy); Riley Dominiak (she/her, ensemble/Connie/others/U/S); Marianne Embree (she/her, ensemble/Mrs. Greer/others); Quinn Frances (she/her, youth ensemble/U/S Molly); David Geinosky (he/him, Rooster Hannigan); Eliza Monté Gilbert (they/them, ensemble/U/S); Desiree Gonzalez (she/her, Grace Farrell); Jimmy Hogan (he/him, ensemble/U/S); Emily Holland (she/her, Lily St. Regis); J’Nae Howard (she/her, ensemble/U/S); Brielle Horwitch (she/her, Pepper/U/S Annie); Rebecca Hutchinson (she/her, youth ensemble/U/S July); Albert Johnston (he/him, ensemble/U/S); Léa Juat (she/her, Kate); Kylie Kaplan (she/her, youth ensemble/U/S Kate); Charlotte Keefer (she/her, youth ensemble/U/S Pepper); Katie Kotila (she/her, ensemble/U/S); Larrah Lambo (she/her, July); Allison Rose Macknick (she/her, ensemble/Mrs. Pugh/U/S Miss Hannigan); Michael Metcalf (he/him, Oliver Warbucks); Jojo Nabwangu (she/her, youth ensemble/U/S Tessie); Asia Posey (she/her, ensemble/Star to Be/U/S); Callan Roberts (he/him, ensemble/Bundles/Bert/others/U/S Rooster Hannigan); Katie Romanski (she/her, youth ensemble/U/S Duffy); Peter Ruger (he/him, ensemble/Drake/others/U/S); Bob Sanders (he/him, ensemble/Franklin D. Roosevelt); Elin Joy Seiler (she/her, Annie); Sarah Smith (she/her, Miss Hannigan); Raymond Cam Truong (he/him, ensemble/U/S); Korey White (he/him, ensemble/Dog Catcher/others/U/S Oliver Warbucks) and Teddy (he/him, Sandy/owner: Jojo Nabwangu).
 
Annie’s orchestra includes Linda Madonia (she/her, piano); Alison Tatum (she/her, violin/concert master); Emily Fischer (she/her, violin); Annika Porter (she/her), viola); Lewis Rawlinson (he/him, cello); Cara Strauss (she/her, reed 1); Lara Regan (she/her, reed 2); Eva Butcher (she/her, reed 3); Greg Strauss (he/him, trumpet 1); Amy Nelson (she/her, trumpet 2); Stephanie Lebens (she/her, trombone 1); Luke Malewicz (he/him, tuba/trombone 2); Mike Locker (he/him, guitar); Eric von Holst (he/him, bass); Justin Kono (he/him, drums) and Tina Laughlin (she/her, percussion).
 
Annie’s creative team includes Kyle A. Dougan (any pronouns, director); Mollyanne Nunn (she/her, choreographer); Michael McBride (he/him, music director); Andrew Lund (they/him, assistant director); Amber Wuttke (she/her, intimacy &amp; violence choreographer); Kathy Logelin (she/her, dialect coach); Erin McCarthy (historian and dramaturg); Alex Villaseñor (he/him, youth advocate); Rachel Rock (she/her, stage manager); Carolyn Goldsmith (she/her, assistant stage manager); Jacqueline Penrod (she/her, co-scenic designer); Richard Penrod (he/him, co-scenic designer); Nga Sze Chan (she/her, props designer); Rachel M. Sypniewski (she/her, costume designer); Kristen Brinati (she/her, wardrobe head); Alice Salazar (she/her, hair, wig and makeup co-designer); Melanie Saso (she/her, hair, wig and makeup co-designer); Chelsea Lynn (she/her, master electrician and board programmer); Anthony Churchill (he/him, media designer); Stephanie Farina (she/her, sound designer); Forrest Gregor (he/him, production sound engineer); Will Hughes (he/him, Andersonville Scenic Studios); Ben Lipinski (any pronouns, Andersonville Scenic Studios); Chris Chase (he/him, production manager) and Katie Meine (she/her, company manager). 
 
Tickets are now on sale from $19.50 to $106 with tickets for guests 25 years old and younger available at half-price at <a href="https://www.musictheaterworks.com/2025-season/annie/" rel="nofollow" target="_blank">MusicTheaterWorks.com</a>.

Local Event: Music Theater Works Presents “Annie,” Dec. 18 - Jan. 4

Skokie

Music Theater Works Presents “Annie,” Dec. 18 -...

Music Theater Works is proud to announce the cast and creative team for the fourth and final production of its 2025 season,...

Music Theater Works Presents “Annie,” Dec. 18 - Jan. 4

College of Lake County - Grayslake Campus (main campus)

The Ruth Page Center for the Arts is proud to present its annual live production of “Ruth Page’s The Nutcracker” featuring original choreography by the legendary Ruth Page and directed by the artistic team of Victor Alexander, Dolores Long, Birute Barodicaite, Dori Rothschild, Chrissy Lacny and Renardo Johnson. The ballet returns to the College of Lake County’s (CLC) James Lumber Center for the Performing Arts, 19351 W. Washington St. in Grayslake, Saturday, Dec. 20 at 1 and 5 p.m. and Sunday, Dec. 21 at 1 p.m.
 
Originally presented at the Arie Crown Theatre from 1965 until 1997, this production recreates highlights from Ruth Page’s beloved original full-length staging. It features exquisite dancing, world-renowned guest artists, stunning costumes and magical settings in the Land of Snow and Land of Sweets.
 
The 2025 production of “Ruth Page’s The Nutcracker '' features a cast curated from local and international dance artists. In keeping with Ms. Page’s emphasis on children’s involvement, additionally cast are students from Ruth Page School of Dance’s Professional Dance and Young Dancer Training Programs.
 
Tickets range from $17.40 to $35 and are on sale now at <a href="https://linktr.ee/ruthpagecenter" rel="nofollow" target="_blank">RuthPage.org</a>.

Local Event: Ruth Page’s “The Nutcracker” at College of Lake County, Dec. 20-22

Lake County

Grayslake

Ruth Page’s “The Nutcracker” at College of Lake...

The Ruth Page Center for the Arts is proud to present its annual live production of “Ruth Page’s The Nutcracker” featuring...

Ruth Page’s “The Nutcracker” at College of Lake County, Dec. 20-22

Stars and Garters Theater

Chicago’s recently opened premier retro entertainment venue, Stars &amp; Garters, 3914 N. Clark St., is pleased to present the New Year’s Eve Spectacular Spectacular! Celebrations begin Wednesday, Dec. 31 at 8 p.m. and conclude Thursday, Jan. 1, 2026 at 3 a.m. 
Stars &amp; Garters showcases their new space by ringing in 2026 with an action-packed celebration spanning six hours. The celebration features singing, dancing, burlesque, magic, comedy and more. The inaugural New Year’s Eve Spectacular will delight patrons as they can roam and rotate throughout the entire space, stopping to enjoy their entertainment of choice. Stars &amp; Garters mixologists will be serving specialty cocktails, including alcoholic and non-alcoholic options. Highlights of the night includes: 
<ul><li dir="ltr">90 minutes of comedy and striptease provided by the bombtastic bombshells of BimBamBoom</li><li dir="ltr">60-minute meet and greet and photo opportunity with Roxy the Sloth</li><li dir="ltr">Champagne midnight toast in the Main Stage with all of the performers' latest hits and a few other surprises designed to get people on the dance floor with a midnight DJ dance party with DJ Adam Black</li><li dir="ltr">Spectacular showgirl photo ops with Ronnie Rouge and Gemini Blackheart</li><li dir="ltr">Two hours of West Coast jazz with the Steve Knight Trio</li><li dir="ltr">Live tarot card readings with Ryan Van Bussum</li><li dir="ltr">Mystifying mentalism from illusionist Nolan Webber</li><li dir="ltr">Succulent and delicious early-evening charcuterie board</li><li dir="ltr">Mid-evening candy and sweet Delights bar</li><li dir="ltr">Late night hot and zesty pizza bar</li><li dir="ltr">A screening of the hit film Moulin Rouge in the Rouge Room</li><li dir="ltr">Plus other wild surprises to make it an unforgettable New Year's Eve </li></ul>
 
Stars &amp; Garters requests that patrons arrive in black or gold attire for the evening.
 Tickets are non-refundable and may be transferred to another patron for no fee. Tickets start at $95.93 and are on sale now at <a href="https://www.eventbrite.com/e/new-years-eve-spectacular-spectacular-tickets-1963637089394?aff=oddtdtcreator" rel="nofollow" target="_blank">EventBrite.com</a> or by calling 773.242.9929. For more information, please contact <a href="mailto:starsandgartersclub@gmail.com">starsandgartersclub@gmail.com</a>.

Local Event: New Year’s Eve Spectacular Spectacular! at Stars & Garters

New Year’s Eve Spectacular Spectacular! at...

Chicago’s recently opened premier retro entertainment venue, Stars & Garters, 3914 N. Clark St., is pleased to present the New...

New Year’s Eve Spectacular Spectacular! at Stars & Garters

Oil Lamp Theater

Oil Lamp Theater is proud to present the first production of its 2026 season, The Outsider, written by Paul Slade Smith and directed by Scott Westerman, January 23 - February 22, 2026 at Oil Lamp Theater, 1723 Glenview Road. 
 
When the sitting governor gets kicked out of office for, you guessed it, corruption, it’s time for someone new to take the throne… uh...the role. And the polls are in, it's time for an outsider. Enter bumbling brainiac Ned Newley. With bright ideas and hope in his eyes, he’s the perfect candidate - on paper. It will take a team of dedicated pollsters, campaign coordinators and more notecards than one can count, to turn him into a poised politician who can expertly avoid questions like it's his job. This knee-slappingly hilarious play will have the audience reaching across the aisle to share a laugh. Audiences may even find a renewed sense of hope for politics…okay maybe not… but they'll at least enjoy an absolutely hysterical and highly entertaining break from the news.
 The performance schedule is Thursdays and Fridays at 7:30 p.m., Saturdays at 3 and 7:30 p.m. and Sundays at 3 p.m. There will be additional Wednesday performances Jan. 28 and Feb. 11 at 11 a.m. and 3 p.m. and Feb. 18 at 7:30 p.m. There will be an understudy performance on Wednesday, Feb. 4 at 7:30 p.m.Tickets are on sale now for $30 for previews and $55 for the run at <a href="https://www.oillamptheater.org/mainstage-productions/the-outsider-" rel="nofollow" target="_blank">OilLampTheater.org</a>.

Local Event: Oil Lamp Theater’s “The Outsider,” Jan. 23 - Feb. 22

Oil Lamp Theater’s “The Outsider,” Jan. 23 -...

Oil Lamp Theater is proud to present the first production of its 2026 season, The Outsider, written by Paul Slade Smith and...

Oil Lamp Theater’s “The Outsider,” Jan. 23 - Feb. 22

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Posting Activity

Lookingglass Theatre Company Presents “Anthony Rapp: Home for the Holidays,” Dec. 17 - 20

DEC

17

7:00 AM

Lookingglass Theatre Company, 163 E Pearson St, Chicago, IL

Music Theater Works Presents “Annie,” Dec. 18 - Jan. 4

DEC

18

7:00 PM

North Shore Center for the Performing Arts in Skokie, 9501 Skokie Blvd, Skokie, IL

Ruth Page’s “The Nutcracker” at College of Lake County, Dec. 20-22

DEC

20

1:00 PM

College of Lake County - Grayslake Campus (main campus), 19351 W Washington St, Grayslake, IL

New Year’s Eve Spectacular Spectacular! at Stars & Garters

DEC

31

8:00 PM

Stars and Garters Theater, 3914 N Clark St, Chicago, IL

Oil Lamp Theater’s “The Outsider,” Jan. 23 - Feb. 22

JAN

24

7:30 PM

Oil Lamp Theater, 1723 Glenview Rd, Glenview, IL

Mold Inspection Chicago — Mr Mold Inspector