Chicago, IL
| Rank | Year | Name | Category | Time |
|---|---|---|---|---|
| 1 | 2022 | Nolan McKenna | M 20-29 | 3:04:49 |
| 2 | 2020 | Wes Judd | M 20-29 | 3:15:09 |
| 3 | 2020 | Kenneth Sprague | M 20-29 | 3:17:30 |
| 4 | 2001 | James Gomez | M 30-39 | 3:17:44 |
| 5 | 2013 | Rich Heffron | M 30-39 | 3:19:03 |
| 6 | 2020 | Matthew Diamond | M 30-39 | 3:19:28 |
| 7 | 2006 | Juan Osorio | M 30-39 | 3:20:41 |
| 8 | 2003 | Kip Kinn | M 40-49 | 3:21:30 |
| 9 | 2009 | Daniel Kittaka | M 20-29 | 3:21:43 |
| 10 | 2003 | Patrick Puckett | M 40-49 | 3:24:44 |
| 11 | 2000 | Mark Sherman | M 30-39 | 3:25:48 |
| 12 | 2011 | Rich Heffron | M 20-29 | 3:27:54 |
| 13 | 2006 | Wynn Davis | M 20-29 | 3:29:08 |
| 14 | 2012 | Matthew Jeromin | M 30-39 | 3:30:56 |
| 15 | 2009 | Yoshinori Yamaji | M 20-29 | 3:31:34 |
| 16 | 2016 | Coree Woltering | M 20-29 | 3:31:34 |
| 17 | 2002 | John Beatty | M 30-39 | 3:32:36 |
| 18 | 2001 | Michael Wille | M 30-39 | 3:32:54 |
| 19 | 2012 | Justin Bland | M 30-39 | 3:34:32 |
| 20 | 2016 | Camille Shiflett | F 40-49 | 3:34:56 |
| 21 | 2007 | Kirk Anderson | M 30-39 | 3:35:00 |
| 22 | 2009 | Patrik Berger | M 30-39 | 3:35:24 |
| 23 | 2008 | Patrick Berger | M 30-39 | 3:35:25 |
| 24 | 2010 | Jeremy Verstraete | M 30-39 | 3:35:41 |
| 25 | 2004 | Mark Konicek | M 40-49 | 3:35:47 |
| 26 | 2010 | Patrik Berger | M 30-39 | 3:35:49 |
| 27 | 2002 | Mark Konicek | M 40-49 | 3:36:27 |
| 28 | 2018 | Lee Jarvis | M 30-39 | 3:36:34 |
| 29 | 2001 | Brian Nach | M 20-29 | 3:37:27 |
| 30 | 2006 | Trey Robinson | M 20-29 | 3:38:10 |
| 31 | 2020 | Mark Eisenman | M 30-39 | 3:38:16 |
| 32 | 2008 | Ted Bowles | M 30-39 | 3:38:20 |
| 33 | 2013 | Aaron German | M 30-39 | 3:38:29 |
| 34 | 2006 | Mark Koniceh | M 40-49 | 3:38:43 |
| 35 | 2012 | Stephen DiSanto | M 20-29 | 3:39:25 |
| 36 | 2002 | Efrain Rodriguez-Juarez | M 30-39 | 3:39:58 |
| 37 | 2017 | Eric Eckerman | M 30-39 | 3:40:50 |
| 38 | 2004 | Kirk Anderson | M 30-39 | 3:40:55 |
| 39 | 2013 | Michael Fetro | M 20-29 | 3:41:16 |
| 40 | 2001 | Robert Ellerbruch | M 20-29 | 3:41:31 |
| 41 | 2013 | James Holt | M 20-29 | 3:41:56 |
| 42 | 2000 | Dean Sprague | M 30-39 | 3:41:58 |
| 43 | 2013 | Meredith Reshoft | F 30-39 | 3:42:26 |
| 44 | 2009 | James Ricker | M 40-49 | 3:43:04 |
| 45 | 2001 | Larry Hall | M 40-49 | 3:44:07 |
| 46 | 2012 | Michelle Mitchell | F 30-39 | 3:44:50 |
| 47 | 2000 | Michael Davenport | M 40-49 | 3:45:05 |
| 48 | 2001 | Michael Davenport | M 40-49 | 3:45:15 |
| 49 | 2023 | Adrienne Eynon | F 40-49 | 3:45:36 |
| 50 | 2011 | Mieczyslaw Swiatkowski | M 20-29 | 3:46:02 |
| 51 | 2002 | Tom Hardies | M 30-39 | 3:46:06 |
| 52 | 2012 | Piotr Janczyk | M 40-49 | 3:46:16 |
| 53 | 2010 | Matt Monroe | M 30-39 | 3:46:38 |
| 54 | 2007 | Eric Youngblom | M < 20 | 3:46:47 |
| 55 | 2007 | Justin Youngblom | M 20-29 | 3:46:47 |
| 56 | 2022 | Jacobus Wijpkema | M 40-49 | 3:46:52 |
| 57 | 2003 | Gary Beck | M 40-49 | 3:46:53 |
| 58 | 2002 | Thomas Swatek | M 40-49 | 3:47:08 |
| 59 | 2008 | Bill Kotaska | M 40-49 | 3:47:17 |
| 60 | 2001 | Howard Kambara | M 30-39 | 3:47:28 |
| 61 | 2001 | Alex Swenson | M 30-39 | 3:47:50 |
| 62 | 2009 | Bob Herskovitz | M 50-59 | 3:48:00 |
| 63 | 2012 | Meredith Reshoft | F 30-39 | 3:48:11 |
| 64 | 2006 | Eric Berlin | M 30-39 | 3:48:34 |
| 65 | 2013 | Shan Riggs | M 30-39 | 3:48:53 |
| 66 | 2001 | Jim Courtney | M 40-49 | 3:48:57 |
| 67 | 2005 | Kirk Anderson | M 30-39 | 3:49:06 |
| 68 | 2018 | Walter Jedzejec | M 30-39 | 3:49:33 |
| 69 | 2005 | Lisa Menninger | F 40-49 | 3:49:38 |
| 70 | 2001 | Vladimir Podzorov | M 50-59 | 3:50:57 |
| 71 | 2019 | Matthew Payne | M 20-29 | 3:50:59 |
| 72 | 2022 | Brian Robinson | M 30-39 | 3:50:59 |
| 73 | 2010 | Kirk Anderson | M 30-39 | 3:51:23 |
| 74 | 2023 | Matt Luff | M 40-49 | 3:52:02 |
| 75 | 2000 | Larry Hall | M 40-49 | 3:52:11 |
| 76 | 2011 | Dennis Remke | M 30-39 | 3:52:38 |
| 77 | 2023 | Christopher Allen | M 50-59 | 3:52:54 |
| 78 | 2013 | Piotr Janczyk | M 40-49 | 3:53:01 |
| 79 | 2000 | Tom Hardies | M 30-39 | 3:53:30 |
| 80 | 2012 | Jennifer Benitez | F 30-39 | 3:53:53 |
| 81 | 2006 | Greg McCarter | M 40-49 | 3:54:28 |
| 82 | 2017 | Jerry Bloom | M 40-49 | 3:55:00 |
| 83 | 2012 | Jeremy Sullivan | M 30-39 | 3:55:05 |
| 84 | 2010 | Ilan Levine | M 30-39 | 3:55:06 |
| 85 | 2013 | Dave Caldwell | M 30-39 | 3:55:10 |
| 86 | 2021 | Brian Robinson | M 30-39 | 3:55:20 |
| 87 | 2022 | Victoria Digiannantonio | F 30-39 | 3:56:03 |
| 88 | 2017 | Walt Jedzejec | M 30-39 | 3:56:03 |
| 89 | 2010 | Beth Moras | F 50-59 | 3:56:09 |
| 90 | 2002 | Rich Smith | M 30-39 | 3:56:10 |
| 91 | 2013 | John Tierney | M 30-39 | 3:56:24 |
| 92 | 2011 | Matthew Brunmeier | M 20-29 | 3:56:38 |
| 93 | 2004 | Justin Faul | M 20-29 | 3:57:07 |
| 94 | 2007 | Michael McPheters | M 40-49 | 3:57:25 |
| 95 | 2001 | Thomas Swatek | M 40-49 | 3:57:28 |
| 96 | 2014 | Eric Baum | M 20-29 | 3:57:38 |
| 97 | 2009 | Piotr Janczyk | M 30-39 | 3:57:38 |
| 98 | 2001 | Mike Terry | M 30-39 | 3:57:44 |
| 99 | 2007 | Jim Cassioppi | M 40-49 | 3:57:45 |
| 100 | 2010 | Amy Botnen | F 20-29 | 3:58:19 |
