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Best Places to Visit In Chicago

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Famous Festivals and Entertainment

Chicago is known for its summer festivals, live theatre and music, especially the blues and classical music.  On the page below we cover the highlights of Chicago's entertainment scene.

Chicago Air and Water Show - Mid-August

Precision flying is just one of the many attractions of the Air and Water ShowThe Chicago Air and Water Show has been providing thrilling, dare-devil aeronautics and water stunts along the shore of Lake Michigan since 1954. Today it entertains crowds of more than two million people a year, making Chicago’s Air and Water Show the largest free show of its kind in the United States. The Show features high-flying acrobatics by performers such as: The U.S. Navy’s Blue Angels, U.S. Army Golden Knights Parachute Team, The Firebirds, Chicago Fire Department Air and Rescue Team and more. The line-up changes from year to year.

The Air and Water Show can be viewed anywhere along the lakeshore between Fullerton and Oak Street Beach, with grandstands set up at North Avenue Beach. For more information about specific dates and times, go to see the official  City of Chicago Tourism site  and search for the "Air and Water Show".

It’s best to take public transportation or walk to the viewing areas. If that’s not possible park at Millennium Park garages and take the shuttle back (see ).

Taste of Chicago (end of June)

Food is so important to Chicago that they have a 10-day lakefront festival devoted to just that. The Taste of Chicago is the World’s largest food festival, serving culinary treats from approximately 70 of Chicago’s popular restaurants to as many as 3.6 million visitors each year. This is foodie heaven – a chance to graze for hours on taste tempting sample size portions of food, from ethnic to elegant to just plain scrumptious. In addition to great food, the Taste also offers music and entertainment, cooking demonstrations and more.

The most popular day to visit the Taste of Chicago is July 3, which culminates with a spectacular fireworks display over Lake Michigan. To purchase food, you must buy strips of tickets at the ticket booths. The Taste of Chicago is usually held for 10 days, beginning on the Friday before July 4th. The best way to get to the Taste of Chicago is to use public transportation or walk. If you must drive, there is parking available at the Millennium Park Parking lots. For further information, visit the  official City of Chicago Tourism Site and search for "Taste of Chicago".

Chicago Blues Festival - June

Chicago has been called “The Blues Capital of the World,” so it is fitting that it is also home to the world’s largest free Blues Festival. For three days every June, more than 500,000 people converge on Chicago’s Grant Park to enjoy music played by some of the best blues performers in the world.

Music is presented on five stages running simultaneously throughout the day and night. Previous festivals have featured such big-name performers as: B.B. King, Bonnie Raitt, Ray Charles and KoKo Taylor. Food and beverages are also available. More information on dates and what's-on can be found at the official City of Chicago Tourism Website , just search for "Chicago Blues Festival".

Jazz Festival - September

The Chicago Jazz Festival has been a Labor Day Weekend tradition in Chicago for more than 30 years. It is the oldest free concert offered by the City . Although its primary venue is a two-day festivity in Grant Park, Jazz is celebrated at other spots throughout the weekend, including Millennium Park’s Pritzker Pavilion, the Chicago Cultural Center and many of the jazz clubs throughout the city.

The concert in Grant Park features big-name jazz headliners, as well as local talent. For more information go to the City of Chicago Tourism Website and search for the Chicago Jazz Festival.


Chicago Theatre

The Chicago Theatre has a stunning interiorChicago Theatre was named “The Wonder Theater of the World,” when it opened in 1921. It was the first elegant movie “palace” to be built in America, and it set the tone for those that followed. Today the theater features live entertainment, and has presented Bill Cosby, Harry Connick, Jr., and Robin Williams.

Once you enter the lobby, with its French Baroque interior (based on the chapel at Versailles), grand staircase (replicating that of the Paris Opera House), and ceiling murals you may forget about the show that you came to see because the true star here is the theater itself.

If you don’t have time to see a show, Chicago Theatre tours are available throughout the year. For tour schedules and show information go to the official website. The Chicago Theatre is located at 175 N. State Street.


Cadillac Palace Theatre

The Cadillac Palace Theatre, at 151 W. Randolph St., is another of Chicago’s former grand movie palaces. It was built as a premier vaudeville house in 1926 with an abundance of brass ornamentation. It is said that during World War II, when the government was confiscating brass from theaters for the war effort, the Palace’s owners ordered that all its brass be painted white to camouflage its presence. It remained hidden that way until renovations in 1999.

During its vaudeville hay-day the Palace featured well known acts like Bob Hope, Jimmy Durante, and Mae West. Today it features many Broadway shows like: Phantom of the Opera, the Color Purple, Wicked and more.  Operated by "Broadway in Chicago", more information can be found here.  

Bank of America Theatre

The Bank of America Theatre (formerly the Shubert Theater) is the oldest theater operating in the City today. It was originally named the Majestic Theater when it was built in 1906, then, renamed the Shubert in 1945.

The theater was built to be a vaudeville house, and remains, today, a popular venue for live musicals and Broadway touring performances. The Bank of America Theater is located at 18 W. Monroe Street. The theatre is operated by "Broadway in Chicago" whose website can be found here.


Second City

Second City and its style of improvisational sketch comedy were almost unheard of when it opened in Chicago in 1959. Today, it is world famous for introducing many talented comedians, including Alan Arkin, Robert Klein, and David Steinberg. With the advent of NBC's Saturday Night Live, other alumni, like: John Belushi, Dan Akroyd, Gilda Radner, Martin Short, John Candy, Mike Meyers and Tina Fey joined the list, as well as others too numerous to mention.

Second City is a cabaret-style theatre located in Piper’s Alley (1616 Wells Street), in an area known as Old Town.  It entertains audiences nightly with a variety of comedy shows from improve to satirical. For information, reservations and directions to the theatre go to  Second City's official website.

Classical Music

Lyric Opera of Chicago

The Lyric Opera of Chicago performs both classic and modern operas. Its season runs from October to March, and it is dark (closed) the rest of the year. If you’re interested in seeing a show, buy tickets early, as  performances are often sold out. For more information on  what's-on, ticket prices and schedules. see the official website . The Lyric Opera House is located at 20 N. Wacker Drive.

Orchestra Hall at Symphony Center

Orchestra Hall at Symphony Center, 220 S. Michigan Avenue, is the home of the Chicago Symphony Orchestra, as well as the hosting many extraordinary orchestras from around the world. Orchestra Hall first opened in 1904 and was named a National Historic Treasure in 1994. The Hall is closed throughout the summer months, when the Orchestra moves to the Ravinia Festival, in the Chicago suburb of Highland Park. For more information, visit the Symphony's official website .


You don't have to look too far to find blues bars in Chicago. You can usually narrow your choices to nearby locations using the local entertainment guides available in most hotel lobbies or by asking the hotel staff for their recommendation on a blues bar that meets your preferences.  Alternatively, the blues bars listed and linked to below are regarded  as some of the finest venues in the Chicago blues scene.

The Loop - Some of the best blues in the city can be found  at Buddy Guy's Legends.

Near North Side -  If you are looking for blues in Near-North, try the House of Blues.

Lincoln Park - This is a great area for listening to the blues, especially along   Halsted Street, where you will find several popular blues bars.  Standouts include  B.L.U.E.S.   and Kingston Mines , although there are many excellent venues scattered throughout the Lincoln Park.


Next section of our Chicago Guide -

Cruises on Lake Michigan and the Chicago River.

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Places  Described On This Page

Air and Water Show
Taste of Chicago
Chicago Blues Festival
Jazz Festival
Chicago Theatre
Classical Music



The Best Places to Visit in Chicago

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