Chicagoland Speedway Pole Winners
Monster Energy NASCAR Cup Series
| Year | Race | Driver | Qualifying Speed |
| 2019 | Camping World 400 | Austin Dillon | 176.263 |
| 2018 | Overton’s 400 | Paul Menard | 180.012 |
| 2017 | Tales of the Turtles 400 | Kyle Busch | 187.963 |
| 2016 | Teenage Mutant Ninja Turtles 400 | – | Qualifying Not Held |
| 2015 | MyAFibRisk.com 400 | – | Qualifying Not Held |
| 2014 | MyAFibStory.com 400 | – | Qualifying Not Held |
| 2013 | GEICO 400 | Joey Logano | 189.414 |
| 2012 | GEICO 400 | Jimmie Johnson | 182.865 |
| 2011 | GEICO 400 | Matt Kenseth | 183.243 |
| 2010 | LifeLock.com 400 | Jamie McMurray | 183.542 |
| 2009 | LifeLock.com 400 | Brian Vickers | 184.162 |
| 2008 | LifeLock.com 400 | – | Qualifying Not Held |
| 2007 | USG Sheetrock 400 | Casey Mears | 182.556 |
| 2006 | USG Sheetrock 400 | Jeff Burton | 181.647 |
| 2005 | USG Sheetrock 400 | Jimmie Johnson | 188.147 |
| 2004 | Tropicana 400 | Jeff Gordon | 186.942 |
| 2003 | Tropicana 400 | Tony Stewart | 184.786 |
| 2002 | Tropicana 400 | Ryan Newman | 183.051 |
| 2001 | Chicagoland 400 | Todd Bodine | 183.717 |
