Sunday in the heart of downtown Chicago. Concrete canyons, rain in the forecast, and absolutely no room for error. This place is NASCAR’s answer to Monaco—just with more fenders and way more attitude. Strategy calls, wet-weather rollouts, drivers clobbering walls like piñatas. Buckle up. Let’s break down the board for the second round of the In-Season Challenge.

 

 

 

The Favorites

Shane van Gisbergen (+200 BetMGM)
Let’s get real—this is his domain. Won the inaugural Chicago race on debut in 2023, dominated Mexico City this year in the rain. He’s basically a street-course cheat code. The price is stingy for a reason, but if it goes green at the end? SVG is the boogeyman.

Christopher Bell (+850 FanDuel)
The stats say he's the biggest threat to ruin SVG’s party. He’s led 51 laps here over two races—no one’s led more. Results? Ugly: 18th and 37th after wrecks. But he won COTA this year, finished second to SVG in Mexico City, and Gibbs gives him real road-course pace. If he stays out of the fence, he’s dangerous.

 

 

 

Mid-Tier Targets

Chris Buescher (+2200 FanDuel)
Mr. Quiet Consistency. Two-for-two in top-10s at Chicago, top-10 in 10 of his last 13 road-course races. This guy isn’t flashy, but he’s lethal on strategy and keeps the car clean while others blow corners. RFK needs a win. They’ll get aggressive if it puts them out front late. If the race gets silly, he’ll be in position.

A.J. Allmendinger (+2500 BetMGM)
Here’s the classic “don’t overthink it” play. Three Cup wins on road courses, a mountain of Xfinity Roval trophies, and Kaulig’s shown flashes of speed at COTA and Mexico City. His two Chicago Cup starts? Trash—best of 17th. But this is a playoff-or-bust scenario for the No. 16, and Allmendinger is exactly the guy who’ll roll the dice on rain tires early and out-strategize the field. Chaos is his love language.

Michael McDowell (+2500 BetMGM)
If you want the veteran street-fighter, here he is. Fifth last year in Chicago. Fifth in Mexico City this season. Always lurking on road courses, always managing tires and brakes better than the hot-shoes. The price is fair, but he’s the best value among the not-quite-favorites if you want a ticket that feels smart, not silly.

 

 

 

Longshot Worth a Look

Todd Gilliland (+15000 BetMGM)
Your classic “let’s make the highlight reel” dart throw—but this isn’t some dumb lotto ticket. He finished 7th here last year, averages 13th across two Chicago races, better than guys like Elliott or Logano. He also has Truck wins in the rain. If the forecast delivers and it becomes a tire-choice clown show, Front Row isn’t scared to gamble. This is the cheap beer bet with real upside.

 

 

 

Props That Pop

Chris Buescher Top-10 Finish (+100 Caesars Sportsbook)
This is the sharp, disciplined play. Two-for-two on top-10s at Chicago. He’s cashed top-10s in 76% of his last 13 road-course races. DraftKings and Caesars have him closer to -110. If you see it at plus money? Don’t overthink it. Hammer.

A.J. Allmendinger Top-10 Finish (+120 Caesars Sportsbook)
High floor for a guy who has to go for broke. He’s stacked 22 career top-10s on road courses alone. Kaulig will do anything to steal a result, especially if the skies open. This number is generous considering he’s one of the best wet-weather drivers in the field.

Todd Gilliland Top-10 Finish (+480 FanDuel)
The true value flyer. Average finish of 13.0 in two Chicago starts. He’s done it here before. FRM has the notebook thanks to McDowell. If rain flips strategy on its head? He’s exactly the type to sneak in while everyone else spins out.

 

 

 

Final Thoughts

Chicago’s street course is pure chaos with a strategy twist. SVG is the class of the field but you’re paying for it. Bell is the risk/reward play with real speed if he keeps it off the walls. Allmendinger, Buescher, McDowell? Veterans who know how to manage the madness and pick up the pieces when others overdrive Turn 1. And if you want to swing for the fences? Gilliland is the rain-soaked rocket to shoot your shot. Don’t bet timid. Mix your exposure, pick your angles, and let’s go hunting for big numbers on Sunday in the Windy City.