11/29/25 LAKEFRONT TRAIL ALERT: The lakefront trail is closed from Oak St. to Ohio St., as is the underpass at Chicago Ave., due to weather conditions. See the Lakefront Trail map here.
Summer in the Parks is not over until the school bell rings again on August 18! Basketball, Skateboarding, Running and Teens in the Park Festival are among the activities teens can enjoy throughtout the summer
School may be starting on August 18, but there are still plenty of programs and events tailored for Chicago youth and teens at neighborhood parks. Highlights include organized basketball leagues, skateboarding competitions, Teens in the Park Festival, and much more.
“Summer is ending soon, and the Chicago Park District remains committed to welcoming youth, teens, and young adults into the parks to enjoy organized competitions and cultural events in neighborhood parks,” said Chicago Park District Superintendent and CEO Carlos Ramirez-Rosa. “Each of the late summer offerings provide youth with a space and platform to flourish as athletes and performers.”
Visit www.chicagoparkdistrict.com/teens-parks to explore upcoming programs and initiatives for teens, adolescents, and young adults in the parks. Highlights include:
TIP Fest (Teens in the Parks) 10th Anniversary
The Chicago Park District is celebrating 10 years of #TIPFest! The Teens in the Parks Festival is a platform for young artists to showcase their creative, performative and musical talents as well as to connect to teen resources. On Saturday, August 30, the event will kick off with local performers followed by the winners of the three TIP Fest auditions at Oakwood Beach, located at 4100 S. Jean-Baptiste Pointe DuSable Lake Shore Drive, to support some of the most talented teens in the city. Singers, rappers, dancers, musicians and spoken word artists will be taking the stage during the free event produced in partnership with the John Walt Foundation. This event is open to the public to come and cheer on their favorite local talent! For details, visit www.chicagoparkdistrict.com/tip-fest.
Football season is on the horizon and Junior Bear Football is a free program that gets young people ages 8 to 13 to hone their skills ahead of the high school, collegiate, and professional levels.
Practice schedules vary by park; however, many players have already taken the field for practice. This year, there are 14 park teams in the Pee Wee division, which accommodates players ages 8 to 10. Additionally, 15 park locations will accommodate players ages 11 to 13 in the Varsity division. The top two teams in the varsity division play at Soldier Field in the Mum Bowl Championship. Click Junior Bear Football offerings for more information. Registration ends August 5, 2025.
Windy City Hoops: Free, Organized Basketball
Windy City Hoops allows teens ages 13 to 21 to participate in free, organized basketball games at 12 sites throughout the Chicago Park District. Games are played twice a week by each team; the league culminates with playoffs and a championship.
Start dates vary by park location, however sessions are taking place now, with the next session beginning August 18, 2025. To enroll, individuals or groups can visit a Windy City Hoops park location to sign-up in-person, or register at Windy City Hoops.
‘Go Grind Day Camp & Friday Night Events
Skaters, BMX, and freestyle scooter riders of all ages are welcome to participate in ‘Go Grind Friday Nights from 4:00 p.m. to 7:00 p.m. at Grant Park Skate Park through September 5 at 150 E. Roosevelt Rd. Each event features trick competitions, races, and music.
See the full schedule of ‘Go Grind skateboarding events.
Citywide Boxing Showcases: Free Live Boxing on Summer Thursdays
The Chicago Park District Boxing Program will present boxing showcases at parks citywide on select Thursday nights now through October, featuring athletes from the 18-neighborhood park boxing gyms.
Participating boxers are 8 to 25 years old and are enrolled in the Chicago Park District boxing program. Follow the link to see the full schedule of Chicago Park District Citywide boxing showcases. To participate in a boxing instructional program during the summer session for the link to Boxing Programs.
‘Go Run: Free, Timed 5K and 1-mile Races
The Chicago Park District and the Chicago Area Runners Association are proud to welcome patrons to the 2025 ‘Go Run Series, which features free, timed 1-mile and 5K races at 12 unique park locations citywide. Patrons of all ages and abilities are invited to move at a pace comfortable for them; strollers, wheelchairs, and other mobility aid equipment are welcome and encouraged.
Each year, the ‘Go Run series allows patrons to electronically track their pace through 1-mile and 5k courses with a racing bib provided by the Chicago Area Runners Association. Participants can track their performance across as many as 34 races throughout the 2025 ‘Go Run Series. Registration opens every Friday at 3:00 p.m. the week prior to each ‘Go Run and closes Friday at 2:00 p.m. the day prior to each ‘Go Run. Registration is available at 'Go Run Chicago.