Political background: Illinois state senator since 2013. POLITICO's coverage of 2020 races for President, Senate, House, Governors and Key Ballot Measures. Illinois’ 14th Congressional District is one of 31 U.S. House districts that Donald Trump (R) won in the 2016 presidential election and a Democratic House candidate won in 2018. The 14th district was represented from 1987 to 2007 by Republican Dennis Hastert, who served as Speaker of the House during the 106th through 109th congresses. Track the 2020 Illinois 14th District Election here. We think the race for U.S. House in Illinois’ District 14 leans toward the Democratic candidate. The 14th District covers portions of seven different counties and typically leans Republican. Hastert resigned from Congress in November 2007 and on March 8, 2008 the 2008 Illinois's 14th congressional district special election was held to fill the vacancy. The 14th District covers portions of seven different counties and typically leans Republican. Here are their responses to questions from the Tribune Editorial Board. Seven Republican candidates are running for their party's nomination in Illinois' 14th Congressional District. Come … All 435 House districts will be up for election on Nov. 3, 2020, and the results will determine the partisan balance of the U.S. House in the … Illinois 14th Congressional District General Election, 2020 Party Candidate Votes % Democratic: Lauren Underwood : 203,209 : 50.67 : Republican: Jim Oberweis 197,835 49.33 Write-in votes Joseph Monack 8 0.00 Total votes 401,052 : 100.0 Unsuccessful bids for the U.S. Senate in 2002, 2004 and 2014, governor in 2006 and the 14th Congressional District in 2008 Live 2020 Illinois election results and maps by country and district. This article is part of our Illinois 2020 election voting guide. Illinois 14th Congressional District Contest January 5, 2021 Contest brought by Republican candidate challenging the 2020 election of Representative Lauren Underwood in Illinois’ 14th Congressional District. Democrat Incumbent Lauren Underwood is running for re-election in 2020. 2020 U.S. House Candidate Questionnaires - Illinois ... James Marter, 14th Congressional District Republican candidate profile .