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T.I.P. Fest will be held on Saturday, October 2, 2021 from 2 p.m. to 6 p.m. at Union Park.
T.I.P. Fest will be held on Saturday, October 2, 2021 from 2 p.m. to 6 p.m. at Union Park.
Photo: Chicago Park District

The Chicago Park District is hosting its 6th annual Teens in the Park (T.I.P.) Fest, an annual talent showcase where emerging artists and musicians will perform live and in-person. The free event will be held on Saturday, October 2, 2021 from 2 p.m. to 6 p.m. at Union Park, 1501 W. Randolph St. 

 The T.I.P. Fest stage provides showcasing opportunities for youth artists, including singers, dancers, poets and musicians, between the ages of 14 and 24 years old. Teens are invited to come out and support local artists as well as enjoy concessions, free giveaways, activities, and more. Two auditions were held at Amundsen and Midway Plaisance Parks this summer to determine who would move on to the T.I.P. Fest stage. Ten artists were chosen by popular vote to compete for cash prizes and T.I.P. Fest fame. The third, second and coveted first place winners will be announced during the event. 1st place will receive $500, 2nd place $250, and 3rd place $150.  Professionals in the music industry will judge the performances.

The following are the ten finalists performing on the T.I.P. Fest stage: 

•    Walt The King 
•    Kasual Ownly
•    Sam the Sentient
•    Nailah 
•    Huey Shaku
•    The Vintage Vigneron
•    D'Zaire 
•    Major Purpose 
•    Rarity
•    Joryin

Headlining the event is artist and songwriter Brittney Carter with direct support from Mother Nature. DJ Ca$hera and DJ Dez will be spinning live during the event.

Participating organizations that will be present at the event to provide teens with resources include the Chicago Park District’s Sports and Wellness Departments, Inferno Mobile, Urban Gateways, Vax Nation, Lurie’s Hospital Adolescent Outreach, TruStar, Lincoln Park Zoo, Music Forward, the Economic Awareness Council, Columbia College, and more. 

T.I.P. Fest 2021 is presented in collaboration with the John Walt Foundation and is supported by the Department of Cultural Affairs and Special Events. This annual event is part of the Chicago Park District’s Night Out in the Parks initiative. For more information, visit

For those unable to make it to the event, stay connected to our YouTube channel ( and social media accounts for highlights of the event. Follow us on Instagram at ‘ChiTeensinthePark,’ and Twitter @TeensInThePark. Stay up to date with our teen programs and events at

In accordance with Be Safe Chicago Guidelines for Parks and Recreation Activities, participants in this activity will be asked to wear a mask and practice social distancing at all times while participating. Patrons who are exhibiting any symptoms of COVID-19 are asked to stay home and join us for an event when symptoms subside.

T.I.P. Fest is presented as part of the Chicago Park District’s Night Out in the Parks series, supported by the Mayor’s Office and Chicago Department of Cultural Affairs and Special Events. Now in its 9th year, the 2021 Night Out in the Parks program presents cultural events year-round in neighborhood parks throughout the city. The Chicago Park District in partnership with over 100 local artists and organizations, present engaging events and performances that enhance quality of life across Chicago and amplify the artistic and cultural vibrancy in every neighborhood. Through multiple disciplines, which include theater, music, movies, dance, site-specific work, nature programs, and community festivals, the series aims to support Chicago-based artists, facilitate community-based partnerships and programs, cultivate civic engagement, and ensure equity in access to the arts for all Chicagoans. To further extend the reach of these cultural, arts and nature experiences, the Chicago Park District has mounted a virtual platform to spotlight the diversity of Chicago’s artistic offerings and provide equitable access to some of these performances for all Chicagoans and visitors alike. For more information on Night Out in the Parks, visit