On March 24, 2021, NASCAR announced that an imaginary street course in the Chicago Loop in Downtown Chicago would be the track for the fifth (and what turned out to be the final) race of the 2021 eNASCAR iRacing Pro Invitational Series. The iRacing event was broadcast live on NASCAR on Fox on Wednesday, June 2. Rick Ware Racing Cup Series driver James Davison would win the virtual Chicago street race. Ever since the announcement of the track's virtual creation for this iRacing event, there had been rumors and speculation that NASCAR would like to make this track a reality and have a street race in Chicago on the Cup Series schedule in the future. On July 7, 2022, Jordan Bianchi from The Athletic reported that an official announcement of a Chicago street race being added to the Cup Series schedule would come on July 19. On June 17, Adam Stern from Sports Business Journal suggested that the Chicago Street Course could replace Road America on the 2023 Cup Series schedule as any street course race would likely replace one of the road course races and Road America did not have a contract to have a Cup Series race in 2023.

On July 19, the official announcement of the addition of the Chicago street race to the Cup Series schedule took place. After the announcement, NASCAR executive Ben Kennedy confirmed Stern's report of the Chicago street race replacing the race the race at Road America on the Cup Series schedule in a question and answer session with the media.

The length of the race and the title sponsor of the race have yet to be announced.