Feel-Good Theatrical Performances for the Whole Family Come to Chicago This Holiday Season

Very few things compare to being transported to magical wonderlands during winter to usher in the holiday season. This December, you and the whole family will be able to be taken back in time and immerse yourselves in classical stories that unleash your imagination and take you to another world. Wondering what we’re talking about?

It’s none other than the multiple theatrical stages of Chicago! This holiday season, you will laugh, cry, feel the triumphs and experience the warmth of family and the holidays by immersing yourself in timeless classics that are coming to stages near you.

Ready to see what Chicago has in store for you? Let’s dive right in!


Fans of the Wizard of Oz will love this classic that takes us back to the origins of the much-loved tale. Long before Dorothy and Toto appear on the scene, a history unknown by many unfolds.

It all centers around two young women. One is a bubbly blonde and the other is born with emerald-green skin. Despite forming an unlikely friendship, the world has already decided for them. One is called “good” and the other “wicked”.

Yes, you guessed it! Wicked is coming to Chicago! Held at the James M. Nederlander Theater until December 4, 2022, you’ll laugh, cry, and think as you’re transported into this fictional tale of friendship and triumph. For two hours and 45 minutes, you’ll be absolutely transfixed by the brains, heart, and courage that are portrayed by the powerful performers.

Wicked is the fifth longest-running show in Broadway history. It initially opened to audiences in 2003 and has grown in popularity across the world. Since then, it has won over 100 international awards, among which are a Grammy Award and three Tony Awards.

What’s more is that it’s been performed in over 100 cities in 16 countries around the world, having been translated in multiple languages and being seen by over 60 million people worldwide.

The Nutcracker

The classic production of The Nutcracker returns to Chicago this year, but this time with a twist! Staged in the Civic Opera House (where the Lyric Opera also resides), featuring music performed by the Lyric Opera Orchestra, audiences will also be wowed by the stunning choreography of Christopher Wheeldon. Performed by the Joffrey Ballet, the production takes place from December 3 to 27, 2022.

For two whole hours and during two acts that are set to Tchaikovsky’s classics, you’ll be able to follow young Marie and the Nutcracker Prince on a Christmas Eve journey that goes back in time. The reimagined performance is a spectacle of sights, sounds, and enchantment.

The mysterious Great Impresario makes an appearance and the lines between fantasy and reality blur together. Marie journeys through the Chicago 1893 World Fair to celebrate the rich cultural heritage of Chicago.

This classic Christmas ballet will feature masterpieces including the “Dance of the Sugar Plum Fairy” and many others.

Luminaire: Cabaret – Awesome Cirque Comedy Cabaret

If you want something different and cool, Luminaire is a must see!

This is a groundbreaking, immersive cabaret experience where raucous comedy, world-class singers, jaw-dropping international cirque stars, and a delectable 4 course feast collide. Described as “dynamic, hilarious and delicious”, Luminaire is a fast paced whirlwind of incredible acrobatics, music and a multi-course feast to wow the senses of every guest.

Luminaire is based on World War II, and the ideas of misfits and a way to escape the outside.

Located in the heart of Chicago’s Theater District, on the 14th floor of the Cambria hotel, which is morphed into an extraordinary Belgian Spiegeltent, guests will be wowed by an ever changing performance, a “cirque du smirque” if you will, that is an amazing combination of song, comedy and acrobatics.  The crowd is part of the show and part of the fun.

The cast has world-class credits, including Cirque du Soleil and Broadway!  Luminaire will star Frank Ferrante, an award-winning actor, comedian, and director best known for his interactive stage comedy, including The Caesar in Teatro ZinZanni, which earned him a Chicago Tribune nod as a top ten performer of the year in 2019, and his PBS national television program Frank Ferrante’s Groucho. The production will also star singer, songwriter, and producer Liv Warfield. Her achievements include a critically acclaimed hit solo album – The Unexpected, a Soul Train Music Award for Best Contemporary Jazz Performance, and performing as part of Prince’s New Power Generation. Liv Warfield has toured with some of music’s biggest names, bringing her unique voice and style to audiences around the world. Luminaire is directed by Dreya Weber, whose aerial design and choreography credits include Magic Mike Live in addition to aerials for Katy Perry, Taylor Swift, Britney Spears, Rihanna, Madonna, Cher, Michael Jackson, Christina Aguilera, Kylie Minogue, and Pink’s 2010 Grammy Awards performance of “Glitter in the Air”. Dreya brings in her unique death-defying grace to dazzle Cabaret ZaZou audiences.

This brilliant show is back in Chicago with dazzling flash and flair. It makes for an incredible evening or afternoon of entertainment that audiences should not miss!

A Charlie Brown Christmas: Live on Stage

Everyone’s favorite holiday classic comes to life in a new touring production of A Charlie Brown Christmas: Live on Stage. Audiences will be reunited with their favorite Peanuts gang – Snoopy, Lucy, Linus, Charlie Brown, and the whole gang. The storyline unfolds to help everyone rediscover the true meaning of Christmas.

This one’s for young and old alike. Based on the 1965 animated television special, A Charlie Brown Christmas has become a holiday favorite. It will be performed against the background music of the soundtrack album by The Vince Guaraldi Trio, which was also originally released in 1965. Since then, it has sold over four million copies and is a tradition enjoyed by many generations.

The performance will run for 90 minutes and will include a 20 =-minute intermission.

A Christmas Carol

Most people will immediately recognize Ebenezer Scrooge’s famous “Bah Humbug” exclamation, and for good reason! A Chicago holiday tradition that has run for four decades since 1978, this year’s performance of A Christmas Carol will take place at the Goodman Theater. To date, around two million theatergoers have immensely enjoyed this performance and many continue to return to relive the holiday magic it offers.

The story of Scrooge and his journey to the past, present, and future show him the real meaning of Christmas where generosity triumphs over greed. Based on Charles Dickens’ timeless tale of hope and redemption, the role of Scrooge will be performed by Larry Yando, who returns on stage for the 15th year running.

The two-hour and 15-minute long performance (with one intermission) has been praised for its amazing sets, gorgeous costumes, and eye-popping effects. Described as the “best Christmas story ever told”, it is suitable for anyone aged six and up.

So many choices!

With so many options around, you and your loved ones will be absolutely spoiled with so many choics this holiday season. Nothing compares to a live stage performance, which enables the imaginations of young and old to run wild and to immerse themselves in the magical world of Christmas.

Of course, these events are best enjoyed in a group, so gather your loved ones to experience the magic of Christmas this year. For adults organizing these events for their families and loved ones, one concern may pop up and that’s the important consideration of everyone getting to the theater at the right time. Because of the potential of unpredictable winter weather in Chicago, as well as the fact that parking will be limited and possibly hard to find, why not spare yourself the trouble and let us take all  the stress away for you instead?

At Bus Connection, we cater to all our guests’ transportation needs. And being specialists in Chicago, we know our way around! We offer different-sized transportation options to get you to and back from the venue safely and in good spirits. So, if transportation and parking for larger groups is a concern, don’t hesitate to reach out to us. We’re right here to help and take one less worry away as you immerse yourself in the magic of the holiday season.