The streets of Chicago kick off the second half of the 2025 NASCAR Cup Series season.
Rain is once again in the forecast for the third straight year here. That means there’s potential for different strategies as well as crashes, which should make things a bit more chaotic if that happens.
That said, it’s not a guarantee of rain, as forecasts are right around 50/50 for rain, trending toward 60% toward the latter portion of the race as of Saturday evening as I write this.
Even without the rain, with only 75 laps scheduled, it means we’re in for a race with only around 50 dominator points tops, so the focus here should absolutely be on place differential and finishing position, of course adjusted for driver salary.
Also, practice had a series of issues and with so few laps, my practice FLAGS data is going to be weighed less than a normal week.
Be sure to check out my NASCAR projections in the NASCAR Models on FantasyLabs, complete with floor, ceiling, median, and ownership projections.
My projections, along with Stephen Young’s from RotoGrinders, are available in our new NASCAR DFS package. You can read more about what the package entails here.
Let’s not skip the best part — my Perfect% metric — a metric that tells you how often certain racers appear in the optimal lineup when running 10,000 race simulations.
And don’t forget about the tools that FantasyLabs has to offer, like our Lineup Optimizer to effortlessly create up to 300 lineups or our Lineup Builder if you like to hand-build your lineups.
So, without further ado, here’s my strategy guide and NASCAR DFS picks for the Grant Park 165 on the streets of Chicago!
Grant Park 165 DFS Core Picks
Instead of calling them cash-game picks, I’ll call them core picks, as these are picks I like in all formats. However, it’s important to note that very often core picks tend to go over-rostered in tournaments, so while they should still be used plenty, it may be prudent to sometimes go underweight on these drivers if you think they’ll be significantly over-rostered.
The guys who didn’t qualify: Unfortunately, cash games are pretty unplayable this week, as four drivers failed to make a real lap and are clear cash-game plays.
Bubba Wallace, Denny Hamlin, Chase Elliott, and William Byron start in the last four spots, and all but Hamlin showed speed in practice.
The only reason Hamlin didn’t is that his engine failed halfway through his first practice lap, before he even got up to speed.
That makes cash games essentially a 2v2 this week, unless you want to dare fading one of these drivers and hope they have an issue. But issues are highly random, so I think avoiding cash games is unfortunately the way to go this week.
Updated on 7/14/25
Grant Park 165 DFS Tournament Picks
Ross Chastain ($8100): My model is exceedingly high on Chastain to the point where I think it’s overdone, but I do directionally agree with it that Ross should have a better day than his projected usage if we replayed this race 10,000 times.
Ross looked decent in practice in the first group, when track conditions were less favorable for speed, and he has had some mixed performances on road courses throughout his career. That means he’s had downside, but also upside, which is what I’m looking for in a tournament setting.
A.J. Allmendinger ($9000): With rain possible, things can happen to create mayhem. Another thing that can happen so close to the playoffs is teams and drivers focus on the point standings and playoff points.
That give Allmendinger a perfect opportunity to gain spots just through strategy, as he’s almost surely focused on the race win by sitting 59 points outside the playoff cut line, which is only likely to trend worse if we get another new winner below the cut line in points.
His best bet is to go on the optimal strategy — especially since Shane van Gisbergen indicated he may stay out for a playoff point — and flip the stages to get track position.
A strong finish will still help Allmendinger in the points, and he would put himself in the best spot to hold off SVG for the win.
By starting 16th, there’s enough place differential there, and Allmendinger is likely the seventh car in the order that is nearly guarateed to flip stages, so he could have really strong track position as early as the start of Stage 2.
Zane Smith ($6000): I’m highlighting Smith here because I firmly believe my model is too low on him, and I’d rather play him closer to, or even above, his projected ownership rather than his projected Perfect%.
Smith was strong in practice, posting a top-half, group-adjusted FLAGS, and has had some solid road and street-course performances throughout the top-three NASCAR national series in his career.
DFS players will be keen to use Erik Jones and Ricky Stenhouse Jr. at double-digit rates, and while I think that’s fine, I don’t believe either of the two have the upside Smith has, although they certainly have a better median result than him.
If you want another alternative, Cole Custer ($6100) starts 23rd and provides similar median and ceiling finishing positions to Stenhouse and Jones, but he should be a bit more under-rostered than those two.
YOU MAY ALSO LIKE
DraftKings NASCAR DFS Picks for Las Vegas: Fantasy NASCAR Strategy and Picks for the Pennzoil 400
DraftKings NASCAR DFS Picks for Richmond: Fantasy NASCAR Strategy and Picks for the Toyota Owners 400
DraftKings NASCAR DFS Picks for Phoenix: Fantasy NASCAR Strategy and Picks for the Shriners Children’s 500
DraftKings NASCAR DFS Picks for Kansas: Fantasy NASCAR Strategy and Picks for the AdventHealth 400
