Cillizza was born and raised in Marlborough, Connecticut. Cillizza attended The Loomis Chaffee School (to which he often refers to jokingly as the "Loomis Chaffee School for the Rich") and graduated in 1994. He attended Georgetown University from 1994 to 1998, where he graduated with a B.A. in English. He currently resides in Falls Church, Virginia with his wife and two children. He is of Sicilian and Irish descent. Cillizza is a supporter of Tottenham Hotspur F.C.
Cillizza began his career at The Cook Political Report and, later, Roll Call prior to joining The Washington Post. For the Cook Report he covered gubernatorial races and southern House races. He wrote a column on politics for Congress Daily. During his four years at Roll Call, which he joined in June 2001, he reported on campaign politics from the presidential to the congressional level, finishing his time at Roll Call as the paper's White House correspondent.
His freelance work has appeared in a variety of publications, including The Atlantic Monthly, Washingtonian, and Slate. He has also been a guest on CNN, Fox News Channel and MSNBC. After multiple guest appearances on the network, he was named an MSNBC Political Analyst, a position he resigned when he accepted a position at CNN. He is also a frequent panelist on Meet the Press.
Cillizza founded the blog The Fix in 2005 and wrote for it on a regular basis until he joined CNN in 2017. The blog's focus is American electoral politics, with Cillizza commenting on gubernatorial, Congressional and presidential elections. He also hosts the weekly Fix live chat. He hosts and oversees a monthly trivia contest called "Politics and Pints" at the Washington, D.C. bar Capitol Lounge.
From 2007 to 2008, Cillizza was a co-host of the MySpace/MTV Presidential Dialogues, which hosted John McCain, Barack Obama, and others in a live-streamed, interactive Presidential event series. Cillizza and fellow The Washington Post columnist Dana Milbank appeared in a series of humor videos called Mouthpiece Theater, hosted by The Washington Post. An outcry followed a video in which, during a discussion of the White House "Beer Summit", they chose new brands for a number of people, including "Mad Bitch Beer" for Hillary Clinton. Both men apologized for the video and the series was canceled.
In July 2012, Broadway Books (a division of Penguin Random House) released his book, The Gospel According to the Fix. Journalist Chuck Todd described it as "a great read and guide for both amateur and professional political junkies alike." Written in a blog-like format, it features lists such as "The 10 Best/Worst Negative Ads", as well as an in-depth look at the "deep personal hatreds that politics provoke" and predictions for the 2012 and 2016 presidential election.
For a number of years, Cillizza has served a regular co-host of The Tony Kornheiser Show.
On April 3, 2017, Cillizza joined CNN as a "political reporter and digital editor-at-large," contributing online and on television. His articles typically lean to the left and are highly critical of conservatives and President Donald Trump.
On June 28, 2017, CNN Politics announced the launch of "The Point with Chris Cillizza." According to the official press release, the new "multiplatform brand" will include "daily columns, on-air analysis, an evening newsletter, [a] podcast, and the launch of trivia night events in Washington, DC."