The Grant Park 165 is taking over the streets of Chicago this weekend. Seeing NASCAR running through the streets of downtown Chicago was fun last year and should be even better this year. With the 2024 Grant Park 165 being just the second edition of the race, what are the other races we can look at? What are the betting strategies we’re using for road courses? Is there anything we can take from the chaos of last year’s race for betting the 2024 Grant Park 165? All that plus the winner predictions and best prop bets for Sunday’s NASCAR race in Chicago.

 

Grant Park 165 Road Course Betting Strategies

Aside from right turns on a road course, the other thing that comes to mind is it’s tough to pass. Over the last 10 road races, not a single winner has come from further back than P8 in the starting grid. So if we’re betting outright winners, we’re looking for drivers starting in the top-10 for sure if not closer than that. Passing is possible mid-pack though as pit strategy and cautions can help pickoff several cars at once. Over the last five road races, multiple drivers a race have moved up from between P12 and P20 starting spots to finish in the top-10. Most of those races didn’t have but a couple of cautions in them as well. Chicago is a different style of road/street race because it’s on the city streets. That by nature means it’s a tighter racing line and surface with almost no runoff areas. We’re saying that to point out that we should expect more cautions in this race than typical road crosses where single car spins don’t usually create yellow flags.

 

Grant Park 165 Winner Predictions & Picks

Tyler Reddick +625 (BetMGM)

Reddick has five-straight top-8 finishes at road courses. That doesn’t even mention the fact that he’s won three such races in the Next Gen car. He started P2 here last year and ran so well that despite getting caught up in a big pile up and finishing P28, Reddick had the fifth-best Driver Rating of the race. Reddick is also coming in angry after a P3 finish a week ago feeling that he could’ve done more. 

Christopher Bell +750 (FanDuel)

Bell led roughly half this race last year after starting P4. He was caught up in issues on track and finished worse than he likely should’ve. That being said, he’s finished P3 and P2 in two of the last four road races and has the second-best average finish in the last 10 road races. That history and consistent speed makes him a threat basically every time the Cup drivers show up to a track like this and that’s not even mentioning the impressive run he’s been on since the start of May.

Chase Elliott +1000 (FanDuel)

Every time we come to a road course, Elliott has to be considered given his record at this discipline. He was off to his best start of a season in his carer prior to the last two races. Is this the race he finds a reset button and gets his first win in the last 10 road races? It’s entirely possible given he’s coming off a P4 finish at Sonoma last time right turns we’re involved and P3 last time at Chicago.

Ty Gibbs +1600 (BetMGM)

Prior to inexplicably wrecking out by his own doing at Sonoma, Gibbs had three-straight top-5 finishes at road courses. He’s won these races in the lower levels of NASCAR prior to coming to Cup as well. Even when he wrecked out at Sonoma, he had started and was running P10 showing speed again. If that same speed and consistency shows up in Chicago, he could be a real threat to get his first Cup win.

Chris Buescher +2000 (FanDuel)

Over the last 10 road races, Buescher has easily the best average finish of any driver in the field. His 7.3 average finish mark is 3 spots better than the next closest. He’s yet to win a race in that span but he’s been tantalizingly close a few times. The same can be said for him in all races this year too. With him needing a win to clinch a spot in the playoffs and coming to a strength-type race could very well be a recipe for success.

Ross Chastain +3000 (FanDuel)

Chastain has been improving his finishes each of the last four road races from P18 to P10 to P7 to P5 at Sonoma. While he’s relatively safe in the playoff picture, he is still looking for his first win of the year to essentially lock himself into the playoffs. If he takes another step forward in finishes on road courses, that puts him in line to threaten for the win late.

 

NASCAR Prop Bets: The Grant Park 165 From Chicago Street Race

Ross Chastain Top-10 Finish +105 (DraftKings)

Chastain has nabbed a top-7 finish in both of the two road races this year and has three-straight top-10s. Chastain has also posted five top-10s in the last eight road races, dating back to the start of 2023. That makes this better-than-even-money lien very intriguing.

Kyle Busch Top-10 Finish +130 (FanDuel) or Top-5 Finish +500 (Caesars)

It might be a rough season for Busch, but that hasn’t kept him from showing up at road races. He finished P9 at COTA and P12 at Sonoma after being wrecked in the closing laps while running in the top-10. Meanwhile in his time at RCR he’s finished in the top-five half of the eight races as well. Both of these lines are tasty for a driver who desperately needs a turn around race this weekend.

Alex Bowman Top-10 Finish +260 (DraftKings)

This line puts his chances of a top-10 finish at 27.8%. However, he’s nabbed two top-8s in the last three road races and has four top-10s in his last nine road races. Those are 66% and 44.4% success rates respectively. He hasn’t been dominate but he has been consistent and this line is too good to ignore that consistency.

Todd Gilliland Top-10 Finish +550 (FanDuel)

Last time out on a road course, Gilliland finished P10 at Sonoma. He also nabbed a P11 in the last road race of last year giving up two top-11 finishes in the last four races. The kind of run he’s been on this year and showing he can hold up on road courses is enough to take a stab at this bet.