The circuit's origins trace to a virtual track created in iRacing for the eNASCAR iRacing Pro Invitational Series in 2021. NASCAR announced on March 24, 2021, that a conceptual Chicago Loop street course would host the fifth and final race of that season's five-race iRacing invitational, broadcast live on Fox on June 2, 2021. The real-world version was first publicly reported to be under discussion with Chicago city officials around the same time.
On July 19, 2022, NASCAR announced the Grant Park 220 as a new round of the 2023 NASCAR Cup Series schedule, replacing the Kwik Trip 250 at Road America. A simultaneous IMSA SportsCar Championship event was announced for the same weekend but was later cancelled and replaced by a NASCAR Xfinity Series race.
The announcement drew immediate political controversy. Chicago City Council members, including Alderman Brendan Reilly of the 42nd Ward where the course was located, objected that they had been excluded from negotiations. Residents raised concerns about road closures over the Independence Day weekend, noise, and proximity to the Art Institute of Chicago. NASCAR negotiated a reported $500,000 flat permit fee plus revenue-sharing on tickets and concessions — terms critics noted were significantly below what comparable Grant Park events such as Lollapalooza commanded.
The course formed a 2.140-mile (3.444 km) loop beginning and ending on Columbus Drive in front of Buckingham Fountain, incorporating portions of Columbus Drive, Balbo Drive, Jean Baptiste Pointe du Sable Lake Shore Drive, Roosevelt Road, Michigan Avenue, Congress Plaza Drive, and Jackson Drive. The layout comprised 12 turns and two bridge crossings over Metra Electric District railway tracks. It closely followed the iRacing virtual layout used in 2021, with minor lane-usage differences at turns 4, 5, 10, and 11.
Roads covered by the course typically closed several days before racing to allow barrier installation and track preparation, and fully reopened within two weeks after the events.
The first on-road races took place on July 1–2, 2023. Both events — the Xfinity Series' The Loop 121 on Saturday and the Cup Series' Grant Park 220 on Sunday — were shortened by persistent thunderstorms throughout the weekend. Concerts headlined by The Chainsmokers and Miranda Lambert were cancelled due to the weather. Despite the disruptions, the event attracted widespread attention as a novel format for NASCAR racing in a major urban setting.
The circuit continued to host the annual July 4th weekend NASCAR doubleheader in 2024 and 2025 under its contract with the city of Chicago. The contract covered three years through the 2025 event. In 2024, Kyle Larson set the Cup qualifying record at 1:27.518 (145.111 mph) and Shane van Gisbergen set the Xfinity qualifying record at 1:29.448 (142.496 mph).
Following the 2025 race weekend, Chicago mayor Brandon Johnson's administration indicated willingness to extend the contract for two further years, but only after exploring a date change away from the Independence Day weekend. Event officials subsequently announced that the race would not appear on the 2026 schedule.
The Chicago Street Course represented NASCAR's most high-profile experiment with temporary street-circuit racing in modern times, taking the series into the heart of one of the largest American cities on a nationally prominent holiday weekend. Its origins in a virtual iRacing layout — designed without expectation of becoming a real track — and subsequent translation into a sanctioned Cup Series venue constituted an unusual pathway from esports concept to top-level motorsport venue.