Chicago, IL
| Rank | Year | Name | Category | Time |
|---|---|---|---|---|
| 1 | 2001 | Dave Dunham | M 30-39 | 2:57:29 |
| 2 | 2009 | Zach Gingerich | M 20-29 | 3:12:03 |
| 3 | 2002 | Chad Ricklefs | M 30-39 | 3:12:15 |
| 4 | 2007 | Jordan Dubow | M 20-29 | 3:12:37 |
| 5 | 2000 | Ryne Melcher | M 20-29 | 3:14:45 |
| 6 | 2022 | Nolan McKenna | M 20-29 | 3:16:05 |
| 7 | 2011 | Matt Flaherty | M 20-29 | 3:16:55 |
| 8 | 2008 | Zach Gingerich | M 20-29 | 3:21:11 |
| 9 | 2019 | Matthew Diamond | M 30-39 | 3:22:24 |
| 10 | 2011 | Damian Bednorz | M 30-39 | 3:23:55 |
| 11 | 2015 | Zack McCormick | M 30-39 | 3:25:09 |
| 12 | 2015 | Andrew Knapik | M 20-29 | 3:25:35 |
| 13 | 2007 | Wynn Davis | M 20-29 | 3:25:59 |
| 14 | 2000 | Jason Doland | M | 3:26:09 |
| 15 | 2002 | Scott Swaney | M 30-39 | 3:26:35 |
| 16 | 2001 | James Gomez | M 30-39 | 3:28:25 |
| 17 | 2014 | Matthew Brooks | M 30-39 | 3:29:08 |
| 18 | 2009 | Dallen Ashby | M 30-39 | 3:29:13 |
| 19 | 2007 | Arturs Bareikis | M 20-29 | 3:29:25 |
| 20 | 2023 | Carson Gill | M 20-29 | 3:29:59 |
| 21 | 2014 | Josh Rogowski | M 20-29 | 3:30:33 |
| 22 | 2000 | Dean Sprague | M | 3:30:46 |
| 23 | 2003 | Ryne Melcher | M 20-29 | 3:30:49 |
| 24 | 2006 | Zach Gingerich | M 20-29 | 3:31:18 |
| 25 | 2021 | Todd Gunter | M 30-39 | 3:31:58 |
| 26 | 2001 | Scott Swaney | M 30-39 | 3:32:16 |
| 27 | 2009 | Dennis Remke | M 30-39 | 3:32:34 |
| 28 | 2015 | Jean-Bernard Flanagan | M 40-49 | 3:32:43 |
| 29 | 2015 | Matthew Brooks | M 30-39 | 3:33:08 |
| 30 | 2002 | Bill Weber | M 30-39 | 3:33:27 |
| 31 | 2000 | John Kiser | M | 3:34:27 |
| 32 | 2011 | Arturo Gamez | M 40-49 | 3:35:52 |
| 33 | 2004 | Petri Huhtala | M 40-49 | 3:37:34 |
| 34 | 2021 | Patrick Thornton | M 30-39 | 3:37:57 |
| 35 | 2021 | Richard Hamilton | M 30-39 | 3:38:47 |
| 36 | 2011 | Patrik Berger | M 30-39 | 3:38:48 |
| 37 | 2004 | Ryne Melcher | M 20-29 | 3:39:00 |
| 38 | 2010 | Patrik Berger | M 30-39 | 3:39:34 |
| 39 | 2000 | Mike Senour | M | 3:39:45 |
| 40 | 2003 | Barry Schliesmann | M 40-49 | 3:39:53 |
| 41 | 2009 | Carlo Gibson | M 30-39 | 3:39:56 |
| 42 | 2009 | Alex Leon | M 30-39 | 3:41:10 |
| 43 | 2002 | Michael Davenport | M 40-49 | 3:43:17 |
| 44 | 2014 | Mark Walsh | M 40-49 | 3:43:20 |
| 45 | 2006 | Arturs Bareikis | M < 20 | 3:43:34 |
| 46 | 2001 | Christopher Lang | M 30-39 | 3:44:10 |
| 47 | 2002 | Dean Sprague | M 30-39 | 3:45:14 |
| 48 | 2007 | Justin Faul | M 20-29 | 3:45:50 |
| 49 | 2002 | Larry Hall | M 40-49 | 3:46:07 |
| 50 | 2011 | Mark Salamasick | M 20-29 | 3:46:28 |
| 51 | 2015 | Daniel Galvez | M 40-49 | 3:46:30 |
| 52 | 2001 | Dean Sprague | M 30-39 | 3:47:01 |
| 53 | 2004 | Barry Schliesmann | M 40-49 | 3:47:51 |
| 54 | 2021 | Matt Collins | M 30-39 | 3:47:54 |
| 55 | 2006 | Lisa Menninger | F 40-49 | 3:48:08 |
| 56 | 2015 | Jason Kirsch | M 30-39 | 3:48:08 |
| 57 | 2019 | Matthew DeBruin | M 30-39 | 3:48:13 |
| 58 | 2001 | Michael Davenport | M 40-49 | 3:48:23 |
| 59 | 2007 | Patrik Berger | M 30-39 | 3:48:45 |
| 60 | 2008 | Leonid Isaev | M 50-59 | 3:49:12 |
| 61 | 2005 | Jeremy Kieser | M 20-29 | 3:49:21 |
| 62 | 2001 | Tim Laird | M 20-29 | 3:49:21 |
| 63 | 2010 | Raymond Peleas | M 40-49 | 3:49:30 |
| 64 | 2014 | Mike Gorman | M 20-29 | 3:49:39 |
| 65 | 2019 | Mark Eisenman | M 30-39 | 3:50:09 |
| 66 | 2013 | Mick Brown | M 40-49 | 3:50:17 |
| 67 | 2016 | Bryce Smith | M 30-39 | 3:50:29 |
| 68 | 2000 | Steve Eller | M | 3:50:30 |
| 69 | 2010 | Charles Mathison | M 30-39 | 3:50:34 |
| 70 | 2001 | Andy Leonard | M 40-49 | 3:50:41 |
| 71 | 2015 | Sean Gill | M 30-39 | 3:50:44 |
| 72 | 2008 | David Curtin | M 30-39 | 3:50:48 |
| 73 | 2006 | Kirk Anderson | M 30-39 | 3:51:01 |
| 74 | 2014 | Stephen DiSanto | M 20-29 | 3:51:05 |
| 75 | 2014 | Vic Ciancetta | M 20-29 | 3:51:06 |
| 76 | 2012 | Jorge Newbery | M 40-49 | 3:51:10 |
| 77 | 2008 | Kirk Anderson | M 30-39 | 3:51:22 |
| 78 | 2007 | Kristin Moehl | F 20-29 | 3:51:48 |
| 79 | 2014 | Jeff Phillips | M 40-49 | 3:52:11 |
| 80 | 2009 | Kirk Anderson | M 30-39 | 3:52:22 |
| 81 | 2001 | Jerry Lyons | M 30-39 | 3:52:32 |
| 82 | 2005 | Kirk Anderson | M 30-39 | 3:52:43 |
| 83 | 2023 | David Carta | M 30-39 | 3:52:45 |
| 84 | 2008 | Patrik Berger | M 30-39 | 3:52:53 |
| 85 | 2009 | Larry Hall | M 50-59 | 3:53:09 |
| 86 | 2012 | Tim Ross | M 20-29 | 3:53:18 |
| 87 | 2005 | Mike Terry | M 30-39 | 3:53:18 |
| 88 | 2011 | Jennifer Benitez | F 30-39 | 3:53:24 |
| 89 | 2002 | Mark Tanaka | M 30-39 | 3:53:26 |
| 90 | 2010 | Jennifer Benitez | F 30-39 | 3:53:34 |
| 91 | 2004 | Kathryn Froehlich | F 40-49 | 3:54:04 |
| 92 | 2005 | Ramiro Munoz | M 40-49 | 3:54:11 |
| 93 | 2001 | Larry Hall | M 40-49 | 3:54:25 |
| 94 | 2007 | Eric Youngblom | M < 20 | 3:54:50 |
| 95 | 2010 | Larry Hall | M 50-59 | 3:55:06 |
| 96 | 2017 | William Gane | M 40-49 | 3:55:07 |
| 97 | 2019 | Adam Ohnesorge | M 40-49 | 3:55:21 |
| 98 | 2002 | Daniele Cherniak | F 40-49 | 3:55:24 |
| 99 | 2000 | Scott Swaney | M | 3:55:32 |
| 100 | 2007 | Michael Davenport | M 40-49 | 3:55:37 |
