Being defeated by New York Euphoria in the Eastern Final (one of the Semi-Finals which included a Skill Test, a 3-on-2 match and a dance competition) at Lingerie Bowl II in 2005 and again at Lingerie Bowl III in 2006, the team never reached the Final.
On September 4, 2009 the Chicago Bliss defeated the Miami Caliente, 29–19, in the first ever game of the LFL at the Sears Centre Arena in Hoffman Estates, Illinois. In February 2010 the Bliss finally reached the championship game at Lingerie Bowl VII but lost to the Los Angeles Temptation. On September 1, 2013 the Bliss won their first championship over the Philadelphia Passion. They would repeat as champions the next year, appear in four consecutive championships including a third title, and win a fourth title in 2018.
The Bliss home venue is Sears Centre Arena. In previous seasons, they have played in Toyota Park in Bridgeview, Illinois, which has been renamed SeatGeek Stadium.
The Chicago Bliss are the LFL team with the most wins and the most championship titles. As of the conclusion of the 2018 season, the Bliss had accrued a record of 40-10-1 and four Legends Cup Championships (2013, 2014, 2016, and 2018). As of the end of the 2019 regular season the Bliss are 40-14-1, still the best record in LFL history.
The Bliss defeated the Miami Caliente, 20–7, to win the Eastern Conference title[1][3] but fell, 27–14, to the Los Angeles Temptation in Lingerie Bowl VII. Professional wrestlerDanielle Moinet also played with Chicago Bliss from 2008 through 2011, where she was cornerback and team captain.[4]