On March 24, 2021, NASCAR announced that an imaginary street course set in the Chicago Loop would serve as the venue for the fifth and final race of the 2021 eNASCAR iRacing Pro Invitational Series. The iRacing event broadcast live on NASCAR on Fox on June 2, 2021, and discussions about translating the virtual layout into a real-world event were reportedly under way with city officials as early as March of that year.
The real event was formally announced on July 19, 2022, as the Grant Park 220, replacing the Kwik Trip 250 at Road America on the 2023 NASCAR Cup Series schedule. An IMSA SportsCar Championship race was simultaneously announced for the support bill but was later cancelled and replaced by a NASCAR Xfinity Series event.
The announcement drew criticism from Chicago City Council members who said they had been excluded from negotiations. Alderman Brendan Reilly of the 42nd Ward, where the course is located, was among those who objected publicly. Financial scrutiny followed: NASCAR was reported to have negotiated a flat permit fee of $500,000 plus $2 per ticket sold and 15 percent of merchandise, food, and beverage revenue — figures described as far lower than fees charged for comparable Grant Park events such as Lollapalooza.
Residents raised concerns about road closures over the Independence Day weekend, event noise, and proximity to the Art Institute of Chicago. NASCAR worked directly with the Art Institute to address potential risks to its collections, and hosted promotional events with city institutions and neighborhood groups in the weeks before racing began.
The course hosted its first official race on July 1, 2023, when the NASCAR Xfinity Series ran The Loop 121, followed by the Grant Park 220 for the Cup Series on July 2. Both races were significantly shortened by thunderstorms and standing water that persisted across the weekend. Concerts by The Chainsmokers and Miranda Lambert, scheduled as part of the event, were also cancelled due to weather.
Chicago's original contract with NASCAR covered three years, running through the 2025 season. Mayor Brandon Johnson, who succeeded Lori Lightfoot following the 2023 Chicago mayoral election, said on July 3, 2023 that the course's future remained under evaluation and that community input was being sought. After the 2025 race weekend Johnson's administration indicated willingness to extend the contract for two further years, but only after exploring a change of date. Event officials subsequently announced on X that the race would not appear on the 2026 schedule.
The circuit was a 2.140 mi (3.444 km) loop starting and finishing on Columbus Drive in front of Buckingham Fountain. The route incorporated Columbus Drive, Balbo Drive, Jean Baptiste Pointe du Sable Lake Shore Drive, Roosevelt Road, Michigan Avenue, Congress Plaza Drive, and Jackson Drive. The layout included 12 turns and two bridge crossings over Metra Electric District tracks. It closely followed the virtual version used in 2021 for the eNASCAR iRacing Pro Invitational Series, with minor lane differences at turns 4, 5, 10, and 11.
As a temporary street course, roads were closed several days in advance of each event for track preparation, then fully reopened within two weeks after racing concluded.
The fastest qualifying times at the venue were set in July 2024. Kyle Larson holds the NASCAR Cup Series qualifying record at 1:27.518s (145.111 mph), while Shane van Gisbergen set the NASCAR Xfinity Series qualifying mark at 1:29.448s (142.496 mph), both recorded on July 6, 2024.
The Chicago Street Course represented a deliberate push by NASCAR to expand its footprint into major urban markets and attract younger demographics. Despite operational and weather challenges, the event ran for three consecutive seasons and produced competitive racing in the heart of one of the country's largest cities. Its removal from the 2026 calendar leaves open the possibility of a return in future years, pending negotiations over timing and community engagement.