The origins of the race trace to a virtual event. On March 24, 2021, NASCAR announced that a simulated Chicago Loop street circuit would host the fifth race of the 2021 eNASCAR iRacing Pro Invitational Series. The iRacing event was broadcast live on June 2, 2021, with Rick Ware Racing driver James Davison winning the virtual race. Following that event, speculation grew that NASCAR might convert the concept into a real-world race.
On July 7, 2022, a report indicated that an official announcement of a Chicago street race would come on July 19, and that it could replace Road America on the 2023 Cup Series schedule. The announcement was made as scheduled on July 19, 2022, with NASCAR executive Ben Kennedy confirming that the Chicago Street Course would replace Road America.
On March 7, 2023, NASCAR announced the race would carry no title sponsor and would instead be named after Grant Park, which borders the circuit. The race was set at 220 miles and 100 laps in length; the Xfinity Series companion event was named The Loop 121 after the Chicago Loop district.
The inaugural 2023 running took place during a rain storm. The start was delayed, and the race ran for only 78 of the scheduled 100 laps before darkness forced its conclusion. Shane van Gisbergen, a triple Australian Supercars champion competing in just his first-ever NASCAR Cup Series race for Trackhouse Racing's PROJECT91 program, won the event after qualifying third. His victory made him the first driver to win on their Cup Series debut since Johnny Rutherford in 1963. The result proved pivotal: van Gisbergen departed Supercars at the end of 2023 and moved to the United States to race full-time in NASCAR, eventually joining the Cup Series as a full-time competitor in 2025.
Following the 2023 race, NASCAR reduced the distance. On October 20, 2023, the series announced the Cup event would be shortened from 220 miles and 100 laps to 165 miles and 75 laps, which gave the race its Grant Park 165 name. The revised distance was slightly shorter than the rain-shortened 2023 race, which had covered 171.6 miles over 78 laps.
The 2024 edition similarly ended under weather-related conditions, with the race shortened to 58 laps due to darkness following a rain delay. Van Gisbergen won again, making him the only driver to win the event during its full run.
On July 18, 2025, officials announced that the race would not return in 2026, though the possibility of a 2027 return was left open.
The Chicago Street Race represented a notable experiment in NASCAR's ongoing effort to diversify its venue portfolio. Street circuits, while common in open-wheel racing, had not previously been part of the Cup Series calendar in the modern era. The event attracted considerable attention from motorsport fans outside NASCAR's traditional audience, partly due to its urban setting in one of the United States' largest cities and partly because of van Gisbergen's debut victory. The rain-affected finishes of both the 2023 and 2024 races became a recurring point of discussion about the challenges of scheduling a street event in a city with unpredictable summer weather.