| 1951 | Todd Cartwright & Sugand Reddy SarsamChicago Navy Pier | HYROX DOUBLES | 1:33:32 |
| 1952 | Maresa KingChicago Navy Pier | HYROX | 1:33:32 |
| 1953 | Mike Schutz & Loren SchutzChicago Navy Pier | HYROX DOUBLES | 1:33:34 |
| 1954 | Arianna Ravelo & Alejandro RaveloChicago Navy Pier | HYROX DOUBLES | 1:33:35 |
| 1955 | Tyler MacdonaldChicago Navy Pier | HYROX PRO | 1:33:37 |
| 1956 | Eliana TorresChicago Navy Pier | HYROX | 1:33:37 |
| 1957 | Melissa StreeterChicago Navy Pier | HYROX | 1:33:40 |
| 1958 | Jamie WisemanChicago Navy Pier | HYROX | 1:33:42 |
| 1959 | Jennica CornChicago Navy Pier | HYROX | 1:33:44 |
| 1960 | Holly Tighe & Maria BitkoChicago Navy Pier | HYROX DOUBLES | 1:33:45 |
| 1961 | Elizabeth SchultzChicago Navy Pier | HYROX | 1:33:48 |
| 1962 | Ottis Lewis IiiChicago Navy Pier | HYROX | 1:33:49 |
| 1963 | Emily Obear & Abbie RumerChicago Navy Pier | HYROX DOUBLES | 1:33:50 |
| 1964 | Emily Tucci & Emma DowningChicago Navy Pier | HYROX DOUBLES | 1:33:50 |
| 1965 | Allyson PellissierChicago Navy Pier | HYROX | 1:33:52 |
| 1966 | Bryn D’Ambrosio & Megan SilvaChicago Navy Pier | HYROX DOUBLES | 1:33:55 |
| 1967 | Kaitlyn O'Callaghan & Lindsay MooreChicago Navy Pier | HYROX DOUBLES | 1:33:55 |
| 1968 | Elaina LamacchiaChicago Navy Pier | HYROX | 1:33:56 |
| 1969 | Josh AlfredChicago Navy Pier | HYROX | 1:33:56 |
| 1970 | Leslie Krueger & Becky DandyChicago Navy Pier | HYROX PRO DOUBLES | 1:33:58 |
| 1971 | Olga SamoylyukChicago Navy Pier | HYROX | 1:33:58 |
| 1972 | Courtney HafemanChicago Navy Pier | HYROX | 1:34:00 |
| 1973 | Kelsey Slayton & Danielle DavidsonChicago Navy Pier | HYROX DOUBLES | 1:34:01 |
| 1974 | Jeniffer IbarraChicago Navy Pier | HYROX | 1:34:04 |
| 1975 | Heather Jensen & Kevin PinaChicago Navy Pier | HYROX DOUBLES | 1:34:05 |
| 1976 | Tom Walpole & Scott Hayduk & Jen Hayduk & Jess WalpoleChicago Navy Pier | HYROX TEAM RELAY | 1:34:05 |
| 1977 | Sarah Boespflug & Chloe StarzChicago Navy Pier | HYROX DOUBLES | 1:34:05 |
| 1978 | Travis AllenChicago Navy Pier | HYROX PRO | 1:34:05 |
| 1979 | Mark SchultzChicago Navy Pier | HYROX | 1:34:08 |
| 1980 | Paul FahyChicago Navy Pier | HYROX | 1:34:09 |
| 1981 | Jennifer NagyChicago Navy Pier | HYROX | 1:34:10 |
| 1982 | Colleen PatrikisChicago Navy Pier | HYROX | 1:34:10 |
| 1983 | Reagan Washburn & Jarrett MackeyChicago Navy Pier | HYROX DOUBLES | 1:34:12 |
| 1984 | Shannon Pecson & Taylor HolderChicago Navy Pier | HYROX DOUBLES | 1:34:13 |
| 1985 | Anthony DalyChicago Navy Pier | HYROX | 1:34:14 |
| 1986 | Abigail Strecker & Daniel DiloretoChicago Navy Pier | HYROX DOUBLES | 1:34:14 |
| 1987 | Connor O'NeillChicago Navy Pier | HYROX PRO | 1:34:14 |
| 1988 | Dave Kelly & Lindsey KellyChicago Navy Pier | HYROX DOUBLES | 1:34:16 |
| 1989 | Sara Adame & Lauren GarstkaChicago Navy Pier | HYROX DOUBLES | 1:34:17 |
| 1990 | Jillian IrishChicago Navy Pier | HYROX | 1:34:18 |
| 1991 | Brock BergholtzChicago Navy Pier | HYROX | 1:34:19 |
| 1992 | Jesse JohnsonChicago Navy Pier | HYROX | 1:34:19 |
| 1993 | Virgil Murison & Natalia PestanaChicago Navy Pier | HYROX DOUBLES | 1:34:19 |
| 1994 | Donato AvenaChicago Navy Pier | HYROX | 1:34:20 |
| 1995 | Chelsey CoulthurstChicago Navy Pier | HYROX | 1:34:20 |
| 1996 | Akile Stuart & Vincent GreenChicago Navy Pier | HYROX PRO DOUBLES | 1:34:21 |
| 1997 | Ashley Borowski & Shaun KramerChicago Navy Pier | HYROX DOUBLES | 1:34:22 |
| 1998 | Christen Babcock & Chelsea WhitakerChicago Navy Pier | HYROX DOUBLES | 1:34:23 |
| 1999 | Mary Elizabeth Finkey & Lauren GarrisonChicago Navy Pier | HYROX DOUBLES | 1:34:25 |
| 2000 | Kevin Ally & Danielle BakerChicago Navy Pier | HYROX DOUBLES | 1:34:26 |