The stakes are high, the streets are slick, and NASCAR is back in downtown Chicago for the highly anticipated Grant Park 165. With 41 entries vying for just 40 spots, the tension is already boiling over for Sunday’s main event. It’s a street course spectacle, full of sharps, tight margins, and zero room for error.

But among those ready to race is one driver who is feeling more than just the adrenaline. He’s confident, experienced, and absolutely fired up, but there’s a unique weight on his shoulders this weekend. While others just want to qualify, he’s focused on something deeper. Proving himself to the fans and a certain hometown sponsor is counting on him to deliver on the sport’s biggest urban stage.

NASCAR’s Ford Mustang takes on Chicago gamble

Wisconsin native Josh Bilicki is making a full circle return with a sponsor from Chicago. He isn’t new to the grind. The 29-year-old racer has carved a unique path through the motorsport ranks, competing across the NASCAR Cup Series, Xfinity Series, and Truck series, as well as sports car racing in IMSA and even SCCA national events. His journey started on two wheels with motocross before he made the switch to go-karts and then cars, building a resume defined not by team size, but pure persistence. Over the years, Josh has run races for smaller operations like Rick Ware Racing, Spire Motorsports, and DGM, earning respect for squeezing the most out of limited resources.

After making his Cup Series debut at Sonoma in 2017, he has tallied 103 starts across nine seasons, earning one top 10 in Cup and four in Xfinity. And his most recent cup entry in the grand Park 165 is backed by pure kick, a Chicago-based energy drink company that’s putting its faith behind him. It’s not just a paint scheme; it is pressure. Speaking to Stephen Taranto, Josh is quite positive about his return. He says, “ You know, I feel like I’m more prepared than ever. You know, running on Saturday in the likely key for cars is definitely going to help me prepare for Cup practice and qualifying. And qualifying to us is obviously super important.”

Josh will pilot the No. 66 Pure Kick Ford Mustang Dark Horse featuring an all-new Blood Orange paint scheme, designed to highlight the boldest flavor in the hydration lineup. For someone who has been part of every NASCAR Cup race run in downtown Chicago, this one hits different. Josh admits the weight that comes with partnering with a hometown brand. He says, “We just need to beat one of the other open cars. So we’re the smallest team by a long shot, you know, with a fraction of the next team’s budget. So people are probably counting us out already.”  

In fact, Josh’s Chicago ties go deeper than sponsor logos. He’s put in serious work behind the scenes, spending hours on professional-grade simulators over the past two years to get dialed into the layout of the city’s 2.2-mile Street course. From iRacing setups to team test-based sim testing, Bilicki has been as hands-on as possible despite the underdog status of his part-time efforts. He very proudly shares, ” I’ve ran every cup race in downtown Chicago. I did a lot of sim work, you know, the last couple of years on real sims. So I feel like physically, I’m prepared, mentally, I’m prepared.” 

But no matter how prepared he is, the challenge is real. The rules are clear: only one open entry can make it through, and for Josh, that means he can’t afford a single misstep. He goes on to say, ” We need to push hard enough to tell us what the car is, what it’s doing, what we don’t like that it’s doing. So, you know, it’s a fine line to walk in practice because, yeah, for us, open car racing on Sunday, if we crash in practice, we’re not going to make the field. So but we also, like I said, want to get enough out of the car.” 

And that’s where the balancing act begins. Practice runs aren’t just warm-ups; they could make or break this entire weekend. It is a mental tightrope that few fans realize exists. Wrecking the car and practice? That’s the weekend-ender for a small team like his. But going too easily could mean missing the critical setup changes they need to make to the field.

NASCAR’s fiercest street fight yet

The Chicago Street race is about to deliver something we haven’t seen in a while: real, old-school qualifying pressure. With 41 cars entered and only 40 spots available, one team is guaranteed to pack up early. Aside from the Daytona 500, it’s the first time since 2018 at Texas Motor Speedway that a DNQ looms in this garage at a regular Cup race. And for underdogs like Josh Bilicki, that’s a whole different kind of heat.

However, he isn’t the only one sweating it out. He’s joined by four open entries chasing just for non-chartered slots: Will Brown, Austin Hill, Corey Heim, and Katherine Legge. Each has a story. Brown is the reigning Australian supercars champion and SVG’s direct successor. He is an Xfinity standout with a bruising road course record. Heim is 23XI Racing’s Truck series phenom, making his Chicago debut. And Katherine Legge? A global motorsport veteran trying to muscle a single-car team into the mix.

Among them, Josh stands out for pure cup series experience. With over 100 starts and two prior trips around Chicago’s street course, he brings familiarity that the others lack. But that’s offset by the fact that he is racing with a shoestring operation; Garage 66 doesn’t have the resources or backup cars the others enjoy. One mistake in practice and it’s game over.

This weekend, qualifying isn’t just another session. It’s a street race, literally and figuratively. For Josh Bilicki, the stakes are sky-high, especially with a local sponsor and a crowd expecting fireworks. And for the first time in a long time, qualifying could be just as thrilling as race day.