The first day celebrates the principle of unity. Local organizations are bringing communities together.
It's a holiday that celebrates the roots of Black culture and the generations to come.
Mother Ozzie Watson brought her two daughters, Octavia and Taylor, to the Bronzeville Children's Museum for the first day of Kwanzaa.
"To have a space where they feel safe and welcome and learn about positivity about themselves," Watson said. "It gives us a sense of community."
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"We want them to understand not only their potential, but the fact that they have worth," Bronzeville Children's Museum founder Peggy Montes said.
That worth was instilled through storytelling, face painting, and coloring at the museum.
Meanwhile a little up north, Malcolm X College kicked off the holiday with some education and entertainment on the Near West Side.
"It's the edu-tainment part. Getting the knowledge as well as being entertained," said Sydney Adams, co-chair of Malcolm X College Kwanzaa.
Kwanzaa, a non-religious holiday, is celebrated for seven days with a focused principle: unity, self determination, collective work and responsibility, cooperative economics, purpose, creativity and faith.
"Building and sustaining communities, one principle at a time, and that's when you are incorporated incorporating them into your daily life," said Barbara Meschino, co-chair of Malcolm X College Kwanzaa.
Whether people who celebrate want to shop or get some of the "edu-tainment," every day of Kwanzaa, Malcolm X College is welcoming the community to come celebrate each of the seven principles.
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Some, like Dominic Moab, owner of Sage and Shea, teach African history through their products.
"My favorite product is the black soap. Okay, my grandmother used to make it when I was young," Moab said. "We create dishes with it, everything. So it touched my heart to sell it here."
Others were also learning this holiday season through the power of song.