Chicago’s Diverse Entertainments: Live Shows, Jazz, Comedy and More! #travel


Chicago’s Diverse Entertainments!

Chicago not only boasts top-notch hotels, world-class museums and restaurant meals you’ll remember for the rest of your life–its nightlife is fantastic.

Visitors will experience a variety of unique and talented performers while staying in the Windy City, from jazz to theatre to blues to ballet. Chicago, like much of America, is busier in the summer.Performances and special events are available all year round in this city though. I booked my holiday to Chicago on Expedia to match up with tickets to some of my favourite shows.

The Blue Man Group

If you’re like me, one of the highlights of your trip will be the evening you experience the Blue Man Group. A troupe of performance artists who mix percussion with comedy and multimedia. Blue Man performers, who have permanent shows worldwide, have had a presence at the Briar Street Theatre in Chicago since 1997. Shows take place one or more times per day and several days per week. So, tickets aren’t difficult to find. When it’s time to go to the theatre, don’t be late. The performers make sure everyone else notices!

Other Comedy

If you don’t fancy a night of experimental music but you absolutely like comedy, skip the Blue Man Group and head to one of Chicago’s award-winning comedy clubs. Catch stand-up comics, improvisational work and other acts at Laugh Factory, The Comedy Bar, Zanies Comedy Club or the Comedy Sportz Theatre. With so many options it can be hard to choose which club to attend. However, if you’re travelling in a family group, the Comedy Sportz Theatre is a good choice because of their all-ages shows. If you really love stand-up, Zanies specializes in it (and sometimes has good offers for discounts in restaurants when packaged with tickets). Meanwhile, Laugh Factory pulls in big name stand-up comedians. It is located in the theatre district and is convenient to the city centre. Also in the downtown area, The Comedy Bar is an affordable option for visitors aged 21 and over.


Chicago is known for its great comedy venues, but jazz and blues are still the most recognized performance art forms in the city. Spending a night out with dinner, drinks and live jazz is one of the best ways to spend your holiday in Chicago. One of the longest-lived and most recognized jazz joints in town is the Green Mill Cocktail Lounge. This lounge was once a gathering spot for Chicago mafia, including famous mobster Al Capone. Kept up in the style of a 1940s bar, the lounge is open daily, with regularly scheduled performances from Monday to Saturday. Come on Sundays to listen to a weekly poetry slam.


Like jazz, blues has been a fixture of Chicago entertainment since the early days of the last century. You can find all styles of blues performed here. One of the most notable establishments for blues performances is Blue Chicago on North Clark Street in the River North entertainment district. Another Chicago staple for blues performances is Rosa’s Lounge. Billing itself as the city’s “friendliest” blues lounge, Rosa’s was named the best blues club in Chicago by the New York Times. Rosa’s is located on West Armitage Avenue about 10 minutes from the downtown.



Theatre lovers in Chicago can indulge at one of the city’s more than 200 stages. The Chicago Theatre, built in 1920s, served as a cinema in the early days of moving pictures. When you’re sitting in the audience, admire the baroque-style interior. But, for a more intimate look at the space, book a daytime tour and go backstage to see walls autographed by noted performers, including Frank Sinatra. Currently, it houses a mix of performances, including drama, music and other styles.

Another option for the best performances in the city is a ticket to one of the productions of Victory Gardens Theatre, which offers premieres of some of the world’s next dramatic hits. This collective of writers and actors have created shows earning six Tony Awards and numerous other accolades. The playwrights of Victory Gardens stage their shows at the Biograph Theatre in the Lincoln Park neighborhood.

Symphony and Dance

Have an appetite for more entertainment?

Music lovers won’t go wrong with a ticket to see the Chicago Symphony Orchestra, which is one of the nation’s top five orchestras and plays at Orchestra Hall. For dance, the Joffrey Ballet has the distinction of being the first ballet company to perform at the White House during the administration of John F. Kennedy. It was also the first company to have a cover on Time Magazine.

If you have the luxury of more time in Chicago, you’ll probably never exhaust your options for new entertainment.

Now, the only question remains, what will you do first?

Let me know, til then–cheers m’deres!


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  1. Great picks! We went to Chicago a few summers ago for a weekend trip, and didn't have time to take in any of these shows. I definitely would do so if we went again, especially Blue Man Group which is a fantastic experience.

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