Best Entertainment in Chicago

Best Entertainment in Chicago

Are you looking for the best entertainment in Chicago? Do you need a good laugh or cry? Whatever your case is, learn about where you can find the biggest names in comedy and Broadway acts performing in Chicago.

Laugh Factory

3175 N Broadway, Chicago, IL 60657

Sun-Thur 11 am-11 pm

Fri & Sat 11am-1am


Established in 1979, the Laugh Factory has received the title, “the #1 comedy club in the country” by USA Today. The first location was in Hollywood, California on Sunset Boulevard, with a second opening in Long Beach in 2008. Jamie Masada, Founder and respected as, “the driving force of the Laugh Factory,” is referred to, “as a pioneer and innovator and is an iconic name on the comedy scene.” His vast experience is greatly revered and recognized, “by the entertainment industry’s top power brokers.” Masada, with stand-up comedic experience of his own, is now, “a sought-after consultant and successful producer of comedy franchises for both film and television.” At fourteen years old, “Masada’s father pawned his beloved accordion to help raise the necessary funds,” to get Jamie to the United States. In 1979, Masada used a $10,000 loan from Neal Israel, a writer, and producer, to open the Laugh Factory on Sunset Boulevard. Today, a laundry list of comedians have graced the stage of the Laugh Factory, with some of the most notable being Jim Carrey, Dave Chappelle, Eddie Murphy, Chris Rock, along with the hundreds, if not thousands, of others. Read about the Laugh Factory’s presence in the press or try your hand at comedy at their next Open Mic event!

Briar Street Theatre

3133 N Halsted St, Chicago, IL 60657


Constructed in 1901, Marshall Fields used the building as the delivery horses’ stable. In 1970, Walt Topel purchased the building off Werner Kennelly Moving and Storage Company. Topel went on to renovate the building for his film production and post-production companies. The theatre has been opened back up to the community in 1985, still being owned by the Topel family today. Interestingly enough, the second floor “actually hangs from the ceiling by large turnbuckles that can still be seen.”  As of 1997, Briar Street Theatre has been known as the “Home of Blue Man Group.” With six hundred twenty-five seats, this is one place you don’t want to arrive late too! Read about the theatre’s “late alarm” and how tardy arrivals receive all the attention. With plenty of upcoming events from the Winner of 2011 Off-Broadway Alliance Awards’ “Audience Choice Award for Best Long-Running Show,” be sure to book your tickets to get the best seats in the house! With over thirty years of performing experience, join the thirty-five million who have witnessed the stage show of Blue Man Group.

Annoyance Theatre and Bar

851 W Belmont Ave, Chicago, IL 60657


Originally known as Metraform in 1987, the name didn’t come to mind until two years later in 1989 when “a few friends and a bottle of tequila yielded ‘The Annoyance’.” The Annoyance has developed more than two hundred fifty shows with six different locations in Chicago and New York. The shows are, “comprised of improvisation, sketch, full-length plays, cabaret, and full-length musicals.” With numerous actors in Annoyance shows, you most likely have seen a good number of them, “on stage, in films, and on television.” The initial show, known as “Coed Prison Sluts,” had a healthy run of eleven years, taking the title of Longest-Running Musical in the History of Chicago. The Annoyance received its reputation by, “being the first improvisational theatre to devote itself to creating full-length plays and musicals from improvisation.” Despite the lack of censorship and structure, The Annoyance took the cake for providing more than one original show each week, going as far as performing thirteen separate shows in the week for multiple weeks! For aspiring actors and writers, sign up for classes or submit your own idea for a show! The bar, theatre, and studios are available for rent when not in use. Take a look at what will be performed next and say thanks to the people that keep the doors open.

Stage 773

1225 W Belmont Ave, Chicago, IL 60657


In 2002, Lukaba Productions was created to supervise several theatre shows with a longstanding circulation. Brian Posen, Creative Director of Lukaba Productions, founded the first Chicago Sketch Comedy Festival in January of 2002 which went on to happen each year and brings in more than one thousand actors putting on almost two hundred shows. Five years later, members of Lukaba Productions, including Brian Posen, “began searching for a home for their productions and to create an artistic utopia by hosting many of the city’s itinerant theater companies.” It wasn’t until another four years in 2011 when Lukaba Productions turned into Stage 773. Stage 773 is proud to house four theaters; a one hundred forty-eight capacity proscenium, one hundred forty-eight capacity thrust, eighty capacity black box, and a seventy capacity cabaret. With a yearly average of five thousand three hundred actors performing for more than seventy thousand attendees, Stage 773 has been hosting theatrical performances for forty-four years!

The Vic Theatre

3145 N Sheffield Ave, Chicago, IL 60657


In 1912, The Victoria Theater was opened after three years of construction and a cost of three hundred thousand dollars (roughly eight million dollars today). The five-story theatre with one thousand five hundred fifty seats of “polished mahogany” had a lobby floor and staircase made of Italian marble. It was created so shows with numerous individual sets and touring acts would have a place to perform. Known now simply as “The Vic,” has proven “to be one of the more adaptable and resilient such buildings in town, all the while remaining a stable anchor in the ever-changing landscape of the Lakeview neighborhood.” Designed by John E.O. Pridmore, moving from England to the United States in 1880, Pridmore is known for the churches, temples, and chapels he designed in Chicago. After trying his hand at theater design, Pridmore had great success and went on to design and supervise the construction of twenty theaters in the Midwest. Due to The Great Depression and the advancement of technology, half of the theaters ended up going out of business. Of the few that remained, “none has lasted longer, maintained it’s originally purposed as a venue for popular entertainment, and retained as much of its original splendor as The Vic.” Vic’s website provides in-depth history, an overview of upcoming shows, and spotlight on Chicago’s In Tune Festival.

Now that you know where to find the best entertainment in Chicago, decompress over our blog articles and learn about other exciting events and happenings in the Windy City!

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