Chicago, IL
| Rank | Year | Name | Category | Time |
|---|---|---|---|---|
| 1 | 2013 | Zach Bitter | M 20-29 | 5:12:36 |
| 2 | 2017 | Geoffrey Burns | M 20-29 | 5:14:55 |
| 3 | 2009 | Oz Pearlman | M 20-29 | 5:25:26 |
| 4 | 2007 | Oz Pearlman | M 20-29 | 5:31:51 |
| 5 | 2011 | Matt Flaherty | M 20-29 | 5:32:25 |
| 6 | 2008 | Oz Pearlman | M 20-29 | 5:41:26 |
| 7 | 2011 | Mark Lundblad | M 40-49 | 5:48:49 |
| 8 | 2006 | Oz Pearlman | M 20-29 | 6:05:09 |
| 9 | 2010 | Shan Riggs | M 30-39 | 6:13:25 |
| 10 | 2007 | Joel Eckberg | M 30-39 | 6:17:49 |
| 11 | 2017 | Tera Moody | F 30-39 | 6:20:22 |
| 12 | 2017 | Maksym Chepeliev | M 20-29 | 6:22:14 |
| 13 | 2023 | Isaac Schuetz | M 20-29 | 6:24:08 |
| 14 | 2008 | Zach Gingerich | M 20-29 | 6:27:44 |
| 15 | 2017 | Shelby Pankratz | M 40-49 | 6:28:27 |
| 16 | 2019 | Walt Jedzejec | M 30-39 | 6:28:32 |
| 17 | 2016 | Maksym Chepeliev | M 20-29 | 6:29:05 |
| 18 | 2006 | Zach Gingerich | M 20-29 | 6:31:50 |
| 19 | 2012 | Shan Riggs | M 30-39 | 6:33:31 |
| 20 | 2012 | Alex Leon | M 30-39 | 6:34:36 |
| 21 | 2006 | Michael Arnstein | M 20-29 | 6:35:19 |
| 22 | 2013 | Zack McCormick | M 20-29 | 6:37:07 |
| 23 | 2008 | Jeremy Verstraete | M 30-39 | 6:38:10 |
| 24 | 2023 | Rachel Burke | F 30-39 | 6:40:01 |
| 25 | 2014 | Luis Fernando Miral | M 40-49 | 6:40:11 |
| 26 | 2014 | Meredith Reshoft | F 30-39 | 6:41:33 |
| 27 | 2011 | Kyle Gulseth | M 30-39 | 6:43:37 |
| 28 | 2014 | Kent Green | M 20-29 | 6:44:19 |
| 29 | 2005 | Mike Hlavek | M 20-29 | 6:44:45 |
| 30 | 2007 | Barry Schliesmann | M 40-49 | 6:44:59 |
| 31 | 2022 | Dan Kittivanichkulkrai | M 40-49 | 6:45:46 |
| 32 | 2006 | Kevin Dorsey | M 30-39 | 6:46:04 |
| 33 | 2012 | Bartosz Wronka | M 30-39 | 6:46:54 |
| 34 | 2011 | Bill Kotaska | M 40-49 | 6:47:01 |
| 35 | 2011 | Mike Geldean | M 50-59 | 6:47:30 |
| 36 | 2012 | Bill Kotaska | M 50-59 | 6:47:50 |
| 37 | 2019 | drew heitman | M 30-39 | 6:47:54 |
| 38 | 2020 | David Carta | M 30-39 | 6:50:31 |
| 39 | 2020 | Adrienne Eynon | F 40-49 | 6:52:54 |
| 40 | 2021 | Jimmy Kasper | M 40-49 | 6:53:12 |
| 41 | 2006 | Jay Hagstrom | M 30-39 | 6:53:39 |
| 42 | 2005 | Ann Heaslett | F 40-49 | 6:53:41 |
| 43 | 2018 | Reade Whitney | M 30-39 | 6:54:09 |
| 44 | 2008 | Jay Hagstrom | M 40-49 | 6:55:01 |
| 45 | 2007 | Jay Hagstrom | M 30-39 | 6:55:06 |
| 46 | 2012 | Wil Kidnew | M 20-29 | 6:56:01 |
| 47 | 2007 | Shan Riggs | M 20-29 | 6:56:03 |
| 48 | 2009 | Connie Gardner | F 40-49 | 6:56:20 |
| 49 | 2017 | William Betts | M 30-39 | 6:58:02 |
| 50 | 2006 | Evan Hone | M 20-29 | 6:58:41 |
| 51 | 2009 | Michael Niebauer | M 40-49 | 6:58:47 |
| 52 | 2013 | Benjamin Macaux | M 30-39 | 6:59:12 |
| 53 | 2023 | Andrew Redden | M 20-29 | 6:59:25 |
| 54 | 2017 | Allyson Turner | F 20-29 | 7:01:00 |
| 55 | 2003 | Barry Schliesmann | M 40-49 | 7:02:33 |
| 56 | 2012 | Roger Prevot | M 50-59 | 7:02:51 |
| 57 | 2012 | Meaghan Iandolo | F 20-29 | 7:03:01 |
| 58 | 2020 | Min Yang | M 40-49 | 7:03:52 |
| 59 | 2014 | Bill Kotaska | M 50-59 | 7:03:55 |
| 60 | 2007 | Donald Zimmer | M 40-49 | 7:04:12 |
| 61 | 2015 | Bill Kotaska | M 50-59 | 7:04:55 |
| 62 | 2007 | Greg Hughes | M 30-39 | 7:05:12 |
| 63 | 2013 | Matthew Mcdonough | M 30-39 | 7:05:40 |
| 64 | 2004 | John Beatty | M 30-39 | 7:05:52 |
| 65 | 2014 | Wil Kidnew | M 20-29 | 7:06:47 |
| 66 | 2006 | Robert Zischg | M 40-49 | 7:06:58 |
| 67 | 2022 | Lucas Schirr | M 20-29 | 7:07:45 |
| 68 | 2013 | Craig Redfearn | M 40-49 | 7:08:36 |
| 69 | 2009 | Bill Kotaska | M 40-49 | 7:11:51 |
| 70 | 2021 | Vincent DiFrancesco | M 20-29 | 7:12:15 |
| 71 | 2011 | Roger Prevot | M 50-59 | 7:12:20 |
| 72 | 2018 | Ivan Antonov | M 30-39 | 7:13:07 |
| 73 | 2012 | Brian Ortell | M 40-49 | 7:13:24 |
| 74 | 2019 | Shelby Pankratz | M 50-59 | 7:13:27 |
| 75 | 2010 | Marisa Lizak | F 30-39 | 7:14:37 |
| 76 | 2021 | Eric Shrader | M 20-29 | 7:14:54 |
| 77 | 2008 | Tony Cesario | M 40-49 | 7:15:08 |
| 78 | 2017 | Callie Vinson | F 30-39 | 7:15:54 |
| 79 | 2016 | Arun Sarkar | M 30-39 | 7:17:50 |
| 80 | 2012 | Maxwell Nelson | M 30-39 | 7:18:16 |
| 81 | 2019 | Caleb Wilson | M 20-29 | 7:18:38 |
| 82 | 2019 | William Betts | M 30-39 | 7:18:38 |
| 83 | 2018 | Rachel Burke | F 30-39 | 7:19:01 |
| 84 | 2016 | Min Yang | M 30-39 | 7:19:59 |
| 85 | 2016 | Bibo Gao | F 30-39 | 7:20:00 |
| 86 | 2021 | Dan Kittivanichkulkrai | M 40-49 | 7:20:25 |
| 87 | 2004 | Connie Gardner | F 40-49 | 7:20:29 |
| 88 | 2016 | James Gardner | M 50-59 | 7:20:50 |
| 89 | 2022 | Rachel Burke | F 30-39 | 7:20:59 |
| 90 | 2013 | Scott Smoron | M 40-49 | 7:21:03 |
| 91 | 2011 | Michael Davenport | M 50-59 | 7:21:52 |
| 92 | 2004 | Brent Ward | M 30-39 | 7:22:49 |
| 93 | 2012 | Benjamin Macaux | M 30-39 | 7:23:30 |
| 94 | 2005 | Jenn Dick | F 30-39 | 7:23:45 |
| 95 | 2012 | Michael Wolkowicz | M 20-29 | 7:24:12 |
| 96 | 2012 | Maria Clementi | F 30-39 | 7:24:31 |
| 97 | 2023 | Brad Krueger | M 30-39 | 7:25:50 |
| 98 | 2013 | Anthony D'Agostino | M 30-39 | 7:25:55 |
| 99 | 2010 | Todd Smith | M 30-39 | 7:27:04 |
| 100 | 2017 | CINDY HUNTINGTON | F 30-39 | 7:27:45 |
