The Chicago Blues Festival has been going strong since its first show in 1984. At the inaugural show, one stage was set up for the entire event, and that was all that was needed at the time. Over the years, as the Chicago Blues Festival gained popularity with the blues community, drawing singers and legends from around the world, the event has turned into the largest blues festival in the world, and the one stage has turned in multiple stages to accommodate the headliners.

Playing the blues at the Grant Park blues festival is a tradition shared by the hundreds of thousand who attend as the festival continues in celebration of the music, blues culture, and the people who play the instruments and sing the soulful and reflective lyrics. Over the years, the Blues Festival in Chicago has been the host to legends including Bo Diddley, Chuck Berry, Ray Charles, John Lee Hooker, Stevie Ray Vaughan. and B.B. King.

In June 2009, the Blues Festival in Chicago celebrates its 25th season of bringing the songs and performers to the city labeled the blues capital. During the past years, many milestones have been accomplished, including in 1993 and 1994, when the Chicago Blues Festival was named as the Best Blues Festival by the Living Blues magazine.

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The Grant Park blues festival is the world's largest free outdoor music festival and continues to be the largest music festival held in Chicago that has a long history with blues music. Some of the performers participating at the Blues Festival in Chicago include Pinetop Perkins, Sharon Jones & the Dap Kings, Bettye LaVette, Bobby Parker, Charlie Musselwhite, and more. Each brings a unique style and sound to the individual stages.

Part of the tradition of the Grant Park blues Festival is the participation of students from the Blues in the Schools program in conjunction with the Chicago Public School system. The educational program began in 1988 and provided students the opportunity to learn about the history and heritage of the blues; the program is available to any public school in Chicago. Not only do the students participate in the Blues in the Schools program, the students write their own music incorporating the heritage of the blues infused with their own style and perform at the Chicago Blues Festival.

The festival begins at 11 am each day and ends at 9:30 pm. Admission is free, and tickets are available to use for purchasing food and drink items. There is no parking available at Grant Park for the festival. Public transportation or taxis are available, or if you are staying at nearby hotels, it is easily accessible by walking, as Grant Park (also home to the famous Buckingham Fountain) is centrally located near downtown Chicago and about two miles from the Magnificent Mile.