Round 2 NASCAR In-Season Challenge Predictions: Picks for Each Matchup at Chicagoland

The NASCAR In-Season Challenge moves on to the second round this weekend at Chicagoland Speedway, with the original field of 32 drivers now cut down to 16. Sunday night’s race will provide an opportunity for eight drivers to advance, coming one step closer to that $1 million prize at the end.

Let’s dive into our NASCAR In-Season Challenge predictions for Round 2 at Chicagoland.

Advertisement

Related: NASCAR Weekend Schedule at Chicagoland

(32) Alex Bowman vs (16) Austin Cindric

Alex Bowman delivered the biggest first-round upset of the NASCAR In-Season Challenge at Sonoma, knocking out No.1-seeded Tyler Reddick immediately. He now heads to Chicagoland Speedway to continue his Cinderella story—a track where he coincidentally is the most recent winner (2019). Bowman is having an up-and-down season, with his 10th-place finish at Sonoma his first top-10 in a points race since Texas Motor Speedway. Meanwhile, Austin Cindric has four top-10 finishes this year and a superior average finishing position in the last six races (20.7 to 22.0). This should be a close head-to-head matchup, but we’re rolling with the “upset” pick here.

Advertisement

(25) Todd Gilliland vs (9) Carson Hocevar

Todd Gilliland has a single top-10 finish this season (sixth place at Bristol Motor Speedway), and outside of that, he’s finishing most races in 17th place or worse. He’s never really shown the skills behind the wheel to compete with top drivers, and the No. 34 car itself doesn’t really have the speed to challenge for a top-10 spot. This should be relatively easy for Carson Hocevar. In the last six races, Hocevar ranks eighth in average finishing position (14.7), and that’s with two road courses in the mix. Back on an oval, we think Hocevar can beat Gilliland by 15-20 spots at the finish.

• Advancing: Carson Hocevar

(12) Chase Briscoe vs (5) Ty Gibbs

We’re getting a few teammates going head-to-head for the second round of the NASCAR In-Season Challenge. Ty Gibbs, who won the $1 million prize last summer, is coming off a third-place finish at Sonoma, where he also won both stages. While teammate Chase Briscoe didn’t fare as well in the stages, he was the only one to provide a legitimate challenge for SVG on the final laps at a road course. So both drivers come into Chicagoland with momentum. In the last six weeks, Briscoe and Gibbs have each delivered three top-10 finishes, so consistent success is a theme for them both. This certainly feels like it could be the closest matchup in the second round, but we’re giving the slightest edge to Gibbs.

Advertisement

(20) Michael McDowell vs (4) Chase Elliott

Michael McDowell easily moved past Bubba Wallace in Round 1, but his path to advancement gets a lot more challenging moving forward. Four of McDowell’s top-10 finishes this season have come on road courses. On ovals, his average finishing position drops considerably. Meanwhile, Chase Elliott gets to return to what feels like a second home. In four career Cup races at Chicagoland, Elliott has the second-best average finishing position (8.8), and he’s finished 11th or better in three of the races. We think the No. 9 car will finish at least 10 spots ahead of McDowell on Sunday night.

(2) Denny Hamlin vs (15) Erik Jones

There are plenty of NASCAR stats, particularly in 2026, that make Denny Hamlin the smarter pick to advance to the third round. The regular-season points leader narrowly survived at Sonoma, avoiding another first-round upset at the hands of Ty Dillon thanks to Dillon’s power-steering issue on the final laps. Hamlin will be elated to return to an oval, and his winning streak on these tracks bodes well for him advancing. With that said, Erik Jones is also driving a Toyota, and we just can’t fight this gut feeling that Jones will find a way to pull off the upset this weekend.

Advertisement

(7) Chris Buescher vs (10) Christopher Bell

There was nothing more impressive in NASCAR this past weekend than Christopher Bell netting the third-most points on the day while navigating the road course with a fractured wrist. While the injury hasn’t fully healed, it is getting better, and moving from that track to Chicagoland will take some of the stress off the wrist. We certainly expect Chris Buescher to provide an admirable challenge for the No. 20 team, but we think Bell can beat him by at least 3-5 spots at the finish.

• Advancing: Christopher Bell

(11) William Byron vs (6) Kyle Larson

We’re not sure what’s wrong with the No. 24 team this season, but the results in 2026 for William Byron feel underwhelming. He has recorded just two top-10 finishes in a points race over the last two months, and his average finishing position this season (16.44) is the worst in his Cup career since 2020. In comparison, Kyle Larson leads NASCAR in average finishing position (7.3) over the last six races thanks to five top-five finishes, and Chicagoland is one of his best tracks. This is just a bad head-to-head draw for Byron.

Advertisement

(14) Shane van Gisbergen vs (3) Ryan Blaney

Shane van Gisbergen has never raced at Chicagoland before, but he will be aided this weekend by a strong qualifying position that should position him to start near the front of the field. Unfortunately for van Gisbergen, Ryan Blaney should also have an equally strong starting spot, and his track record on intermediate courses far surpasses van Gisbergen’s.