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Preview: Round 2 of the 2026 In-Season Challenge at Chicagoland Speedway

Nathan Solomon

Brett Farmer | Getty Images

It's time for Round 2 of the 2026 In-Season Challenge as the NASCAR Cup Series heads to Chicagoland Speedway on Sunday (6 p.m. ET, TNT Sports, truTV, HBO Max, MRN Radio, SiriusXM NASCAR Radio) for its first visit to the Joliet, Illinois, facility since 2019. With how Round 1 played out, the expectations are even higher for the only 1.5-mile track in this year's bracket. While the entire right side of the bracket was chalk at Sonoma Raceway, the left side featured three upsets -- including top-seeded Tyler Reddick losing to No. 32 Alex Bowman after an early mechanical issue. To add insult to injury, Reddick lost the series points lead for the first time all season. No. 25 Todd Gilliland also upset No. 8 Daniel Suárez despite finishing outside the top 25, and crafty road racer Michael McDowell defeated No. 13 Bubba Wallace. Three of the 16 Round 1 matchups were decided by two spots or fewer. This week features a handful of matchups between heavy hitters that could ultimately make or break your bracket. Chicagoland certainly has unknowns from sitting dormant for seven years, but generally, expect the cream to rise to the top just like a typical intermediate race. RELATED: Check your bracket! | In-Season Challenge hub ROUND 2 MATCHUPS: TRACK BREAKDOWN It's difficult to predict exactly how Chicagoland will play out, but expect significant tire conservation efforts. The revived speedway features its original racing surface since opening in 2001, and Cup Series teams will have 12 sets of Goodyear rubber for the weekend. Races where tires are at a premium tend to favor veteran drivers, so look no further than Denny Hamlin. He's the best remaining seed and faces No. 15 Erik Jones, who's on an upswing over the summer months. But Hamlin has a whopping 2.5 average finish on intermediates this season with an average running position of 3.89. Hamlin also participated in a Goodyear tire test at Chicagoland this spring with Kyle Larson and Ryan Blaney. And speaking of Larson, he owns the best average finish in six starts at the track (6.17), with Hendrick Motorsports teammate Chase Elliott right behind him (8.75) in four starts. Sunday could be busy on pit road over 267 laps, but all trends seem to favor Joe Gibbs Racing and Hendrick Motorsports. 23XI Racing should also be strong, but none of the Hamlin-co-owned cars remain in the bracket. MATCHUP OF THE WEEK: (No. 6) Kyle Larson vs. (No. 11) William Byron This matchup has some serious star power, and yeah, they're teammates, too. A pair of the best on intermediate tracks, Larson and Byron will square off in Round 2 at Chicagoland -- both coming off relatively decisive wins at Sonoma Raceway. Larson stomped Riley Herbst in Round 1, finishing fourth while the 23XI Racing driver placed 30th. Meanwhile, Byron finished 12th at the road course compared to 21st for opponent Ricky Stenhouse Jr. Hendrick Motorsports is seemingly off on pace at larger ovals this season, at least compared to Toyota -- this year's benchmark. But both Larson and Byron showed plenty of life in recent weeks at Michigan International Speedway and Pocono Raceway. Larson's riding a streak of five top fives in the last six races. With a third-place finish at Pocono, the "Tricky Triangle" served as arguably Byron's best race of the season. So as the 2026 campaign inches toward The Chase, this head-to-head battle could serve as an important marker for Hendrick with both drivers looking for their first wins of the season. On paper, Larson has the advantage, with more momentum and a stronger record at Chicagoland -- a track dormant since 2019 -- but this matchup could be a nailbiter. MORE: Recap Round 1 action [caption id="attachment_517342" align="aligncenter" width="1300"]Getty Images[/caption] KEY MATCHUP: (No. 5) Ty Gibbs vs. (No. 12) Chase Briscoe Another teammate matchup, this time inside Joe Gibbs Racing -- and it should be just as entertaining as the Hendrick drivers. Gibbs is enjoying a career-best season, sitting fourth in the series ranks with a win at Bristol Motor Speedway this spring and the fifth-best average finish (13.17). On the other hand, Briscoe is finally beginning to surge after a brutal spring stretch, recording top 10s in four of the last seven races and nearly outgunning Shane van Gisbergen last weekend at Sonoma. Neither driver has raced in the Cup Series at Chicagoland, and Gibbs hasn't raced at the facility at all. Briscoe has four previous starts in lower series, including an ARCA Menards Series win in 2016. That experience honestly might not be relevant in the Next Gen car, but it's at least something. Overall, Gibbs has shown more consistency in 2026 and has top 10s in three of the first four 1.5-mile races this year. This is as big a toss-up as you can get, but with the No. 19 team heading in the right direction, Briscoe may have a slight edge -- and he could hand Gibbs his first-ever In-Season Challenge loss. KEY MATCHUP: (No. 7) Chris Buescher vs. (No. 10) Christopher Bell This battle might be less heralded than the others, but it could very well come down to the wire. Buescher is one of the most consistent drivers in the series, earning nine top 10s through 18 races and finishing outside the top 20 just three times. Bell is quite the opposite in a season defined by feast or famine, with three finishes outside the top 20 in just the last four weeks. But when the No. 20 JGR team has a clean race, he's almost always a contender. Bell has earned six top-five finishes this season and continues to nurse a broken wrist -- although his P5 effort at Sonoma shows it isn't inhibiting him from logging marquee finishes. His ceiling is generally higher than Buescher's on a week-to-week basis, and with Toyota's stellar intermediate speed in 2026, Bell should be the favorite in this matchup. But if his day starts to unravel, Buescher will almost certainly take advantage. UPSET WATCH: (No. 3) Ryan Blaney Blaney has data from the spring tire test in his back pocket, but faces No. 14 van Gisbergen in Round 2, who's fresh off a victory last weekend at Sonoma Raceway. SVG is clearly improved across the board in 2026, as evidenced by his +5.6 gain in average finish compared to this time last year. But specifically, van Gisbergen has shown an ability to perform well at larger tracks when he has a favorable qualifying draw. This weekend, he'll be the fifth-to-last driver to roll out for a hot lap. The qualifying metric is weighted between the team's finish in the prior race and owners' points. After finishing second at Circuit of The Americas in March, he earned a favorable draw and ultimately finished 11th. He then won at Watkins Glen International in May, followed by a pair of top-10 qualifying results at Charlotte Motor Speedway and Nashville Superspeedway. He finished 11th and fifth in those events, respectively. Meanwhile, Blaney is third in points, yet Ford's pace remains off at intermediates. The No. 12 Team Penske driver is usually the best of the bunch, but he hasn't finished better than seventh all year at traditional ovals 1.5 miles or larger. Blaney is favored here, but it's a dangerous matchup for the 2023 Cup champ.