NASCAR is in Chicago this week for its singular and spectacular Chicago Street Race. Raising the stakes of an already unpredictable race: It’s the second round of the In-Season Challenge, which got off to a bracket-shredding start in Atlanta. The No. 1 and 2 seeds are both out, with upsets all the way down the seeding, too. No Trackhouse or Penske drivers are left, and Ty Gibbs is the only JGR driver still in it.

And now the series is headed to a street course where upsets and chaos are expected even without the Challenge thrown in.

In other words, Chicago should be quite the day of racing.

Our NASCAR experts, Jeff Gluck and Jordan Bianchi, are here to demystify this second round, make predictions for the rest of the tournament, and break down their picks and long shots for the outright winner of the Grant Park 165.

Take it away, guys!

How to watch the NASCAR Chicago Street Race

  • Race: Grant Park 165, Challenge Round 2
  • Location: Chicago Street Course
  • Time: Sunday, July 6, 2 p.m. ET
  • Watch: TNT

NASCAR Cup Series at Chicago Q&A

On to the In-Season Challenge Round 2! Can you bring us up to speed (sorry) on the results from Round 1 and where the field stands now? Any surprises?

Jeff: The chaos bomb at Atlanta was even bigger than anticipated. It took every previous race winner this season out of the tournament in Round 1; the only 2025 winner is Chase Elliott, who won that Atlanta race. It decimated most everyone’s brackets as seven of the top eight drivers in the point standings are already out of the tournament. Three of the top four seeds in the tournament itself are gone, too. Kind of silly, since it was all caused by one big wreck. But anyway, Round 2 does have some great matchups. The best one is Ty Gibbs vs. AJ Allmendinger, since they are both terrific road course racers, and the race is on the Chicago Street Course this week. The Alex Bowman/Bubba Wallace matchup is also really strong.

But the biggest headline is that most of the Cup Series stars are no longer in the tournament after one week.

Jordan: That explosion you heard coming from Hampton, Ga., was everyone’s bracket going boom. Literally. Not a single person has a correct bracket after last week’s race, according to NASCAR. Team Chaos prevailed.

So, let’s update your predictions for the next round of the challenge and the final results. Who you got?

Jeff: If you gave me a fresh slate, my picks for this round would be: Brad Keselowski over Ty Dillon, Alex Bowman over Bubba Wallace, John Hunter Nemechek over Chase Elliott, Erik Jones over Ricky Stenhouse Jr., Ryan Preece over Noah Gragson, Tyler Reddick over Carson Hocevar, Ty Gibbs over AJ Allmendinger and Chris Buescher over Zane Smith.

Then my revised final four (since three of my picks are already gone) would be Bowman, Nemechek, Reddick and Gibbs – with Reddick as my champion (since I picked him to start the tournament).

Jordan: Keselowski over Dillon, though Dillon continuing on as the Cinderella darling isn’t out of the realm of possibility, considering road courses are a style of track Keselowski has long struggled on. Bowman over Wallace. Elliott over Nemechek. Jones over Stenhouse. Preece over Gragson. Reddick over Hocevar. Allmendinger over Gibbs, though this matchup is very much a toss-up. And Buescher over Smith. My revised final four: Bowman, Elliott, Reddick and Buescher. And my new champion pick is Elliott, who uses his high-level consistency to top-10 his way to the title.

Who is your favorite to win at Chicago?

Jeff: Oh my, what a GIANT favorite Shane van Gisbergen is. Having +200 odds might be the lowest we’ve seen in some time, and certainly one of the biggest gaps between drivers (Christopher Bell is next with +725). It’s obvious why people would want to pick SVG, and they’re probably right in doing so. But for the sake of being different, I’ll just go with Gibbs. He was SVG’s closest competition in Mexico City until an ill-timed caution ruined his race, and he’s +1100 to win his first career Cup Series race. Not a great value since that is tied for the fourth-best with Reddick and Elliott, but I’m trying to give you a non-SVG pick here.

Jordan: SVG is the obvious choice, sure. That makes sense. But as last year showed, Chicago is a track where chaos often reigns, and it doesn’t take much to be knocked out of the race, which is what happened to SVG when another driver lost control and crashed into him. All this said, his ability on road courses is remarkable, and if he avoids the likely calamity that has defined this race, he should be in contention for the win.

Who is a long shot you like?

Jeff: They’re not exactly long shots, but Michael McDowell and AJ Allmendinger could absolutely win this race, and they’re +2500. If you want to get really crazy, don’t overlook Will Brown at +3500. Who is Will Brown, you ask? Well, he is the reigning champion in Australia’s Supercars — the same series which gave us SVG and that incredible 2023 Chicago victory in his NASCAR debut. Supercars drivers have a lot more experience on tight street courses than normal NASCAR drivers, so it wouldn’t be a shock at all to see Brown run competitively for Kaulig Racing this weekend, where he’ll be teammates with Allmendinger. You can also get Brown at +125 for a top-10 finish, so maybe that’s a better route.

Jordan: Chris Buescher at +2000 has a lot of value considering how good he typically runs on road courses, including outdueling SVG last year at Watkins Glen. He’s a bona fide contender on Sunday. And if you’re looking for a “deep sleeper,” consider Bubba Wallace at +25000. Wallace was running ahead of last year’s winner Alex Bowman when Bowman inadvertently ran into Wallace exiting the pits and effectively ruined Wallace’s race. Had that not happened, who’s to say Wallace doesn’t win instead of Bowman?

Race winner odds for NASCAR’s Grant Park 165

Betting/odds links in this article are provided by partners of The Athletic. Restrictions may apply. The Athletic maintains full editorial independence. Partners have no control over or input into the reporting or editing process and do not review stories before publication.

(Photo by Jared C. Tilton / Getty Images)