What began as a bold experiment in city-center racing has quickly become of of NASCAR’s most talked-about events. Since its debut in 2023, the NASCAR Chicago Street Race has redefined motorsports in Grant Park, transforming iconic city streets, such as Michigan Avenue and Columbus Drive, into a 2.2-mile, 12-turn adrenaline-fueled circuit. Drawn initially from iRacing concepts, the course quickly became NASCAR’s only true urban challenge, combining tight walls, changing grip levels, and a mix of high-speed straights and sharp city corners. Despite weather hiccups during its 2023 debut, the event earned critical acclaim, boosting Chicago’s profile and giving urban fans a front-row seat to stock-car drama.
The 2025 instalment once again packed Grant Park with racers and spectators. Under blistering summer sun, drivers faced relentless challenges, including eight-car pileups, Austin Cindric’s stalling mid-race, and Cody Ware’s late-race collision. And then came the showstopper. Shane van Gisbergen’s historic sweep, leading 27 laps in Xfinity and 26 in Cup to become the first foreign-born driver to achieve such a feat in Chicago. With Cup cars speeding past Buckingham Fountain and slicing through the city’s core, the event was hailed as a “love letter” to Chicago by race officials.
While the event has been successful in making a splash and attracting new viewers, NASCAR hasn’t inked a deal with the Windy City to continue the street racing festivity. And for the time being, both parties are being mute on any updates.
NASCAR’s Chicago extension is being discussed behind closed doors
As outlined in the official agreement between NASCAR and the City of Chicago, the racing body has the option to extend the event to two additional years (2026 and 2027) by providing written notice within 90 days following the prior year’s race. That means NASCAR executives have until early October 2025 to file the necessary paperwork to secure a 2026 race, provided they are not in default. Still, despite this procedural clarity, public sentiment and political will may present far bumpier terrain ahead.
During this year’s Chicago edition, Mayor Brandon Johnson sidestepped direct questions about the race’s return while making appearances along pit road. Rather than commit to a firm answer, he deflected the conversation to the unpredictable weather, which loomed large over race weekend. “Right now, we’re just going to talk with God and make sure we keep the clouds back,” Johnson quipped. “That’s the most important conversation right now… When I get done praying, and the weather holds up, then we’ll have a conversation afterward.” His remarks, though lighthearted, reflect the broader uncertainty surrounding NASCAR’s future in the Windy City.
On the other hand, Ald. Brendan Reilly (42nd) acknowledged that real conversations with NASCAR are imminent. “Obviously, we know that there’s a two-year extension that needs to be discussed,” Reilly said. “The administration’s going to sit down with NASCAR in the coming weeks to try to work that out.” While Reilly admitted that the event has become popular, he emphasized the need for any extension to be a fair deal that preserves taxpayer value and neighborhood quality of life. “I think local aldermen… want to make sure that it remains a good deal for Chicago taxpayers and that NASCAR continues to uphold its high standards for protecting quality of life and those concerns,” continued Reilly.
Chicago alderman: “Obviously, we know that there’s a two-year extension that needs to be discussed. The administration’s going to sit down with NASCAR in the coming weeks to try to work that out. Certainly it’s become a popular event in Chicago.” @SunTimes https://t.co/dnSctwpu2C
— Adam Stern (@A_S12) July 7, 2025
When the NASCAR Cup Series arrived in Chicago in 2023, the city’s leadership called the street race a “love letter” to the city, by Julie Giese, president of the Chicago Street Race, and then-Mayor Lori Lightfoot. NBC broadcasters echoed the sentiment during coverage of the inaugural event, portraying the fusion of stock cars and skyscrapers as a cultural gift. But three years later, some residents are asking whether the love was ever mutual. With major lakefront access blocked off for weeks and even Independence Day fireworks delayed to accommodate the race, frustrations have started to bubble over.
Citing the inconvenience of road closures, disrupted local tradition, and a lack of cultural resonance with stock car racing, local editorials also questioned whether NASCAR had truly won over the city, “Before you motored into our lives, we never knew we needed auto racing on our beloved lakefront. That’s because we didn’t need it.” Even lighthearted moments, like Derrick Rose sweating in leather jackets as grand marshal, became symbols of awkward cultural fit rather than seamless integration.
For NASCAR, the clock is ticking, not just to file paperwork for a contractual extension, but to win back goodwill from residents who feel increasingly alienated. Whether Chicagoans want a work-defined environment or high-horsepower drama, one thing is clear: the city’s patience for disruption is wearing thin. As editorials put it, “These last few years, things have been moving too fast. If only the same could be said about the cars on the race course.” If the relationship does end, maybe absence will make the heart grow fonder, or at least open up the lakefront for some long-missed July traditions.
Underdogs rise again as In-Season Tournament Bracket collapses in Chicago
After a bracket-busting weekend in Atlanta, fans hoped the chaos would settle, but Grant Park 165 delivered more madness. Shane van Gisbergen cruised to victory, but behind him, the In-Season tournament bracket was turned upside down once again. After the Atlanta chaos, the streets of Chicago also pulled off some big upsets as the field now shrinks down to the final 8 drivers heading into the Sonoma race weekend. Ty Dillon advanced further after Brad Keselowski had to park his car, getting caught in an early wreck.
From the very beginning of the Chicago race, chaos reigned. Just 4 laps in, a crash triggered by Carson Hocevar took out him and Keselowski, giving Ty Dillon and Tyler Reddick an unexpected pass to the next round. Dillon’s confidence showed when he even took a jab at Keselowski on X afterward. As journalist Jeff Gluck of The Athletic pointed out, the upcoming Sonoma round now features a stunning lack of front-runners: “A look at Round 3 of the #NASCAR In-Season Challenge at Sonoma, which has none of this season’s race winners remaining and only two of the top 10 seeds left.” The next matchups are eyebrow-raising, with #8 Alex Bowman vs. #32 Ty Dillon; #12 John Hunter Nemechek vs. #20 Erik Jones; #15 Ryan Preece vs. #23 Tyler Reddick; and #6 Ty Gibbs vs. #14 Zane Smith.
Among the advancing drivers, Ty Gibbs showed the strongest pace, finishing second to SVG and outperforming the road-course specialist AJ Allmendinger. Meanwhile, Zane Smith ran a clean race to place 14th and outlast Chris Buescher, who fought engine issues throughout. John Hunter Nemechek edged past Chase Elliott to advance with a 15th-place finish, setting up an all-Legacy Motor Club showdown with Erik Jones, who snuck in despite a 25th-place run. As the bracket heads to Sonoma, the $1 million question is no longer who is the best, but rather who survives.
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