Name: BYOB Holiday Lights Trolley
Start: 2026-11-27T16:00:00-06:00

Experience Chicago’s top holiday sights like never before!
Climb aboard a vintage BYOB trolley for a one-of-a-kind ride through the city’s most iconic holiday landmarks. Your night kicks off at Matilda, where festive decor and a complimentary chili bar set the tone. Then, it’s off to explore sparkling sights like Christkindlmarket, The Magnificent Mile, Millennium Park’s Christmas Tree, and Lincoln Park ZooLights—ZooLights admission included with your trolley ticket!
Please note: stops are not guaranteed and may vary nightly based on traffic, timing, and availability.
You’ll enjoy music, trivia, prizes, and holiday cheer all night long, with a tour guide leading the way and a souvenir gift to take home.
Book your trolley ride today and light up your holiday season!

Local Event: BYOB Holiday Lights Trolley

Chicago

Cook County

Chicago Metropolitan Area

Illinois

BYOB Holiday Lights Trolley

Experience Chicago’s top holiday sights like never before!
Climb aboard a vintage BYOB trolley for a one-of-a-kind ride through...

Join Guido Kury, M.D., Germany, as he introduces a natural approach to help and healing through the Teaching of Bruno Groening, who&nbsp;taught about a natural power that can help with life issues and bring
peace, happiness and inner freedom. Guests will be shown how to
connect to this energy and people will share their
medically-documented testimonies. 
Admission is free, though donations are appreciated.

Local Event: A Path to a Healthy Body & Soul

A Path to a Healthy Body & Soul

Join Guido Kury, M.D., Germany, as he introduces a natural approach to help and healing through the Teaching of Bruno Groening,...

DANK Haus German American Cultural Center

4740 N Western Ave, Chicago, IL 60625 
Meet the Artists and Teachers of the 2026 Cabaret Connexion! Light dinner is included in the ticket price. Guest list includes a variety of Chicago and global performers including Josephine Baker’s private secretary and local dignitaries.&nbsp; Burst into song and come to the cabaret!&nbsp;
<ul><li>General Admission – $25 </li><li>VIP – $50 </li><li>Full time conference, Connexion Passport, Flexpass Donor – prepaid RSVP required</li></ul>Official website: cabaretconnexion.org#cabaretconnexion #chicagomusic

Local Event: Cabaret Connexion Artist Meet & Greet Evening Soirée at DankHaus Chicago

Cabaret Connexion Artist Meet & Greet Evening...

4740 N Western Ave, Chicago, IL 60625 
Meet the Artists and Teachers of the 2026 Cabaret Connexion! Light dinner is included in...

Cabaret Connexion Artist Meet & Greet Evening Soirée at DankHaus Chicago

Virtual

City Winery Chicago Presents An Evening with Anthony Rapp live on Monday, November 2nd at 7:30 PM!
Anthony Rapp invites audiences into an intimate evening of music, memories, and storytelling, sharing the songs that have shaped his remarkable life and career. A celebrated actor and singer, Rapp originated the role of Mark Cohen in Jonathan Larson’s groundbreaking RENT, earning an OBIE Award alongside the original cast. From Broadway and Off-Broadway to film and television, including his beloved role as Lieutenant Commander Paul Stamets in Star Trek: Discovery, Rapp has built a career defined by powerful performances and authentic storytelling.
For this special engagement, Rapp will perform selections from his favorite repertoire, including Broadway classics and songs that have personally resonated with him throughout his journey. Joined by Daniel A. Weiss on keyboard and Lee Moretti on guitar, he will also share stories and reflections from a career spanning decades.
Doors Open: 6:00 PM

Local Event: An Evening with Anthony Rapp

An Evening with Anthony Rapp

City Winery Chicago Presents An Evening with Anthony Rapp live on Monday, November 2nd at 7:30 PM!
Anthony Rapp invites...

American Writers Museum

Longtime independent bookstore owner and AWM Founding Board Member Roberta Rubin stops by to discuss her new memoir Turning Pages: The Life and Times of a Bookseller. For more than thirty years, Rubin owned and ran The Book Stall at Chestnut Court in Winnetka, Illinois—one of the nation’s most admired independent bookstores. In this warm and inspiring memoir, she reflects on the journey that transformed a neighborhood shop into a nationally respected cultural destination and a beloved cornerstone of community life.
Rubin will be interviewed by writer Richard Reeder. Books will be available for purchase and Rubin will sign them following the program.More about Turning Pages:
A leader in independent bookselling, Rubin championed emerging and established writers, cultivated generations of passionate readers, and steered her bookstore through every challenge the shifting literary landscape presented—from big-box competition to the rise of online retail. Her story is filled with engaging anecdotes about the authors, publishers, colleagues, and customers who shaped her world, offering a behind-the-scenes look at the relationships and determination that sustained an independent bookstore through decades of change.
Both a deeply personal account of a life devoted to books and a source of inspiration for booksellers and independent shop owners, this memoir reflects the same energy, warmth, grit, and unwavering commitment to books that defined her oversight of the store. It testifies to the power of independent retailers to build community, spark curiosity, and bring people together—and to Rubin’s ongoing advocacy for the enduring value of bookstores and the written word.
ROBERTA RUBIN owned and ran The Book Stall at Chestnut Court for more than three decades, turning it into one of the most influential independent bookstores in the country. The store, in Winnetka, Illinois, won accolades including Publishers Weekly’s Bookstore of the Year in 2012. Rubin helped chart a course for indie bookstores to survive and thrive against the rise of big chain bookstores and Amazon, emphasizing author visits, community outreach and personalized service. She is also a member of the founding board of the American Writers Museum, where a room is named in her honor. She currently lives in Evanston, Illinois.RICHARD REEDER was born and raised in Chicago and continues to live in the Chicago area with his wife Anne. Educated in the Chicago public schools, he has two degrees from Roosevelt University. His multifaceted career included working as a caseworker, elementary school teacher, employment counselor, research assistant, and as an executive in both government and social service and educational organizations. Richard remains active as a consultant, writer, and adult education facilitator and instructor.

Local Event: Author Talk: “Turning Pages” by Roberta Rubin

Author Talk: “Turning Pages” by Roberta Rubin

Longtime independent bookstore owner and AWM Founding Board Member Roberta Rubin stops by to discuss her new memoir Turning...

Gateway Lounge

Experience an enchanting evening direct from Paris featuring Isabelle Georges joined by the Kevin King combo for 'Oh La La!'. This spectacular cabaret performance is followed by an International Song Fest directed and hosted by Lou Ella Rose.Gateway Lounge at Copernicus CenterFree lot parking, near 90/94 Highway#livemusic #cabaretconnexion #chicagomusic

Local Event: Isabelle Georges Oh La La! with Cabaret Connexion 

Isabelle Georges Oh La La! with Cabaret Connexion 

Experience an enchanting evening direct from Paris featuring Isabelle Georges joined by the Kevin King combo for 'Oh La La!'....

Main Stage, City Winery Chicago, 1200 W Randolph St, Chicago, IL, 60607

City Winery Chicago Presents LA Young's Phyllis Hyman Tribute live on Tuesday, November 3rd at 7:30 PM!
LA Young's Phyllis Hyman Tribute&nbsp;brings the music of one of soul and jazz’s most distinctive voices to life in an unforgettable live performance.
If you love the timeless music of Phyllis Hyman, this is a tribute built for true listeners. LA Young is a contralto, sharing the same rare, rich, low-toned vocal range that made Hyman’s performances so captivating. Rather than an impersonation, Young delivers Hyman’s songbook in the range it was written for, backed by her working band, Soul Society™, with every arrangement performed live and nothing on tape.
After three consecutive years of performances and three sold-out nights at the Anacostia Playhouse, LA Young is bringing this celebrated tribute beyond the capital. She has also shared the Jazz Legacy Foundation Gala stage with leading jazz and soul performers and was a three-category 2018 Maryland Music Awards nominee.
An independent tribute production. Not affiliated with or endorsed by the Estate of Phyllis Hyman<a href="https://eventvesta.com/events/165427/t/tickets" rel="nofollow noopener" target="_blank">View Tickets</a> &amp; More Info

Local Event: LA Young's Phyllis Hyman Tribute

LA Young's Phyllis Hyman Tribute

City Winery Chicago Presents LA Young's Phyllis Hyman Tribute live on Tuesday, November 3rd at 7:30 PM!
LA Young's Phyllis...

Biograph Theatre, 2433 N. Lincoln Ave., Chicago, IL 60614 

For more than four decades, the Tony Award-winning musical Little Shop of Horrors has delighted millions of fans around the world with the funny and frightening story of the shy shop assistant, his coworker crush and a mysterious, carnivorous plant. Written by the powerhouse team of Howard Ashman and Alan Menken (Disney’s The Little Mermaid, Beauty and The Beast and Aladdin), Little Shop of Horrors takes audiences on a wild trip where love and world domination meet at a Skid Row floral shop. 

Little Shop of Horrors plays November 4 – December 13 at the Biograph Theater, with performances on Wednesdays, Thursdays and Fridays at 7:30 p.m., Saturdays at 3 and 7:30 p.m. and Sundays at 3 p.m. Single tickets are reserved seating and are on sale for $28 - $98 at PorchlightMusicTheatre.org or by calling the Porchlight box office at 773-777-9884.

Local Event: Porchlight Music Theatre’s Little Shop of Horrors 

Porchlight Music Theatre’s Little Shop of Horrors 

For more than four decades, the Tony Award-winning musical Little Shop of Horrors has delighted millions of fans around the...

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BYOB Holiday Lights Trolley

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