Chicagoland Tri Series Challenge

Registrants must maintain a USA Triathlon Annual Membership.

Chicagoland Tri-Series Challenge

We’re excited to announce the Chicagoland Tri-Series is here! Join in a new tri-state triathlon challenge to complete the “BEST OF THE MIDWEST” triathlon experiences at Leon’s Triathlon, the Pleasant Prairie Triathlon, and the Chicago Triathlon!

BEST OF THE MIDWEST

Leon's Triathlon

Join us on Saturday, May 31, and Sunday, June 1, 2025, for Leon’s Triathlon, America’s Race! Known as the premier paratriathlon and military tribute race, this event brings together athletes of all abilities, from first-time competitors to elite paratriathletes and military veterans.

Leon’s Triathlon isn’t just a race—it’s a celebration of resilience, dedication, and American spirit. Whether you’re racing, volunteering, or cheering, you’ll be part of something bigger.

Pleasant Prairie Triathlon

Get ready for an unforgettable race experience this June 22 at the Pleasant Prairie Triathlon, set against the stunning backdrop of Prairie Springs Park! Begin your journey by diving into Lake Andrea, a pristine 100-acre spring-fed lake, where the swim portion of the event kicks off. Pedal through scenic routes in the Village of Pleasant Prairie, featuring a new frontage road with exhilarating long straightaways. Finally, lace up your shoes for the run, where you’ll traverse a combination of paved and gravel paths winding through the beautiful Prairie Springs Park.

Chicago Triathlon

Offering Kids, SuperSprint, Sprint, Olympic, and Triple Challenge categories, the Chi Tri is one of the world’s largest and most accessible triathlons. From first-timers to seasoned veterans, kids to grandparents, age-group competitors to paratriathletes, the Chicago Triathlon has an experience for everyone on the shores of Lake Michigan.

Join us this August 23-24 in Chicago.

What Is It?

The Chicagoland Tri-Series is a new tri-state triathlon challenge to complete the “BEST OF THE MIDWEST” triathlon experiences at Leon’s Triathlon, the Pleasant Prairie Triathlon, and the Chicago Triathlon!

Start your season at one of the unique and patriotic races in the country at LEON’S TRIATHLON, which also serves as the exciting MILITARY & FIRST RESPONDER’S NATIONAL CHAMPIONSHIPS. Then continue your racing season and compete for the title of Wisconsin State Champ at the PLEASANT PRAIRIE TRIATHLON. Finally, finish off the challenge at the largest tri in the USA and compete for the title of Illinois State Champ at the CHICAGO TRIATHLON!

As an added bonus, the USA Triathlon (USAT) national and state championships provide an opportunity for a higher percentage of finishers to qualify for the USAT AGE GROUP NATIONAL CHAMPIONSHIPS which is coming back to Milwaukee, WI in 2025 and 2026!

The primary goal of the “CHICAGOLAND TRI-SERIES” (CTS) is participation – to motivate, accelerate, and celebrate triathlon becoming more accessible and fun for athletes of all ages and ability levels! All three races have historically been recognized as some of the three largest ADAPTIVE & PARA TRIATHLON supportive races in the country – helping to make triathlon more accessible in the midwest thanks to our partnerships with the Dare2Tri Paratriathlon Club.

Join us in inspiring participation for a wider range of athletes of all ages, backgrounds, and adaptive ability levels to get into the great sport of triathlon!

Why Participate?

Get ranked by USA TRIATHLON (USAT) in the NATIONAL RANKINGS when you complete three USAT sanctioned races!
Support more ADAPTIVE, PARA, MILITARY, and FIRST RESPONDER friendly races!
Get inspired by the patriotic experience at the MILITARY & FIRST RESPONDERS NATIONAL CHAMPIONSHIPS at Leon’s Tri!
Compete in the Wisconsin STATE CHAMPIONSHIP at the Pleasant Prairie Tri!
Race in one of the WORLD’S LARGEST TRIATHLON events at the Chicago Triathlon!
Compete for State Championship INDIVIDUAL AGE-GROUP, HIGH SCHOOL, and CLUB TEAM titles!
Qualify for the USAT NATIONAL CHAMPIONSHIPS and compete for a spot on the TEAM USA age group team to race in the patriotic “stars & stripes” uniform at a World Championships!
Earn a special Stuff We All Get (SWAG) item for completing the series! (SWAG announcement coming soon!)
Enjoy a unique tri-series finish line experience at the Chicago Triathlon with the race directors from all three events as you earn your prize to celebrate your summer racing season!