Grant Park 165: Chicago DFS and Betting Picks
Hello NASCAR fans! Brian and Kyle are in to get you set for the Grant Park 165 as NASCAR invades downtown Chicago. Consider subscribing to this newsletter if you have yet to do so. Also give Brian and Kyle a follow for more NASCAR betting and DFS thoughts in 2025!
Feel free to fade or follow any or all of the following plays/picks. For a more extensive breakdown of the bets and DraftKings picks, check out this weeks episodes on YouTube! If you have questions or want to chat NASCAR, hit us up on Twitter, comment on YouTube, or on this article.
As a reminder, only bet what you can afford to lose. If you think you may have a gambling problem call 1-800-Gambler.
DraftKings Values
Brian’s Targets
Ty Gibbs | $9,300 Starting 9th
If you caught our pre-practice show, you know both Kyle and I were high on Ty entering the week. This optimism was rewarded with an awesome practice where the 54 posted the 4th fastest lap and had the 2nd best 5 and 10-lap averages. That, in addition to his past performances here in Chicago and what we saw in Mexico, seem to indicate another amazing Sunday for Gibbs. Starting 9th presents a good opportunity for placement points, especially in the event he does find the front as was the case in Mexico.
Will Brown | $7,300 | Starting 19th
He didn’t “flash” or post a blazing qualifying time, but Brown’s steady improvement during saturday’s sessions is exciting. The Supercars driver looked really good in his first Cup Series start last year at Sonoma before an equipment failure ruined the day. He’s in, what I would consider better equipment than that race here in Chicago, and should only get better as the day goes on. That, along with the threat of rain, something he should handle well, likely minimizes his disadvantage versus the field as well. As you’ll see on my betting card, I think Will Brown has some decent upside this week.
Katherine Legge | $4,500 | Starting 33rd
Yeah, she’ll be the slowest car on track this week, but that may work to our advantage like it did in Mexico City. There, Katherine ran her own race and her own pace to a 32nd place finish after starting dead last. Obviously, starting further up is slightly worrisome, but her lack of competitive speed, in theory, should keep her away from battles which could promote wrecking. All we need here, especially considering most DFS players will steer clear of Legge, is a clean race with her getting to the finish line. If that happens, a finish near or around her starting spot, will be worth the ability to squeeze the likes of Byron and Elliott into lineups.
Kyle’s Targets
William Byron | $10,000 | Starting 39th
This week Team Hendrick gives us not one, but two incredible options on DraftKings. Both the 24 and 9 were unable to qualify and will be starting in the back of the field. Will the 24 come into the vast majority of contests with a massive roster percentage? Sure, but it's totally worth it.
In practice, Byron was arguably the best car prior to his contact with the wall. In his two starts at Chicago, the 24 car has finished 7th and 13th after starting in the 20s. Same goes his start at Mexico where he came home 9th after starting 27th. While it may be hard for Byron to find victory lane without a bit of craziness, he clearly can move forward and reward those who roster him this week.
If you want to fade his massive ownership with hopes of an incident or staying stuck deep in the field, I wouldn't fault you. From a GPP perspective, a bad run from the 24 could separate you from the field in a massive way. But it feels like a thin bet. For me Byron is the good chalk we should all jam in even at an elevated price tag.
Chase Elliott | $9,500 | Starting 39th
How do you not love Chase Elliott on DraftKings this week? The 9 car is coming off of a win for the first time since April of 2024. Elliott is also coming off of an impressive showing in Mexico, making up serious time to finish 3rd.
This week Elliott will be starting 39th which opens up a massive opportunity for scoring points on DraftKings. Much like his teammate, the 9 car will come with a sizable roster percentage but for good reason. His form is the best it's been in a while and he just showed how good he can be on this track type.
Like the 24 car, Elliott can be faded at your own risk. Sure it gets you off of a driver with massive ownership but this week whatever the number is might still be underused. The potential downside is minimal and the upside is meteoric. In cash, you have to start with the 9 and 24 in all lineups.
Todd Gilliland | $6,500 | Starting 20th
The Gillygang rejoice because the 34 is very much in play this week. If we are loading up on expensive backmarkers on DK, targeting value is much needed to make lineups work. While Austin Hill, Cole Custer and Bubba Wallace all tickle my fancy, Gilliland shows up more often on this style track than many may realize.
In his two Chicago starts Gilliland has finished 19th and 7th. In Mexico City he started an impressive 7th and was top 5 after Stage 1. However he was unable to sustain that run and ended up 22nd.
Obviously starting 20th requires the Pickle man to not only sustain but flirt with a top 10 finish. It doesn't feel like that is an absurd ask. Especially when you consider the projected ownership compared to some of the other names in his range. Buckle up with the Todd father this week.
Chalkcago Cash Targets
GridRival Pick Slips
We have partnered with GridRival for the 2025 NASCAR season where you can get a 100% deposit bonus of up to $100 when using Code AOP25.
Below you will find some of our favorite values on GridRival. It really feels like a great week to get exposure places that are not the betting window. Feel free to combine your favorite options below or fade them if you think we are WRONG.
Favorite Firekeepers Casino 400 Bets
Brian’s Play
Will Brown Top 10 +350 (FanDuel) 1u *Would bet down to +250
Like Shane Van Gisbergen, Brown is a Supercars champion, and very familiar with street/road course racing. This was evident early in his lone Cup Series start at Sonoma last year before succumbing to that dastardly equipment failure, as he looked to be a real threat inside the top 10.
Making Brown even more interesting, is how similar he thinks the Chicago layout is to street courses on his regular Supercars schedule, something SVG has also talked about.
Another layer to this Brown market is the fact he’s not racing for points and will always be making strategy calls to maximize his finish. With weather in the forecast once again, and odds not moving much post-qualifying, I’m not rushing to bet much of anything on Cup regulars or guys with short numbers. Brown doesn’t fall into either category, and could even surprise late in the race if the cards flop correctly.
Kyle’s Play
Toyota to win +240 (Bet365) 5U
Chicago is setting up to be a race best spent as a fan and not a bettor. SVG looked incredible on Saturday both in practice with the Cup drivers and in the Xfinity race going toe to toe with Connor Zilisch. His odds are insanely short for the Grant Park 165 and they may be correct. Another 10 plus second victory is very much in the range of outcomes on Sunday. That is if we don’t get another race affected by rain.
So with an incredibly short favorite and a potential for showers I am targeting Toyota to win the race. If you told me SVG doesn't win, I would pencil in a handful of toyotas including Christopher Bell, Tyler Reddick and Ty Gibbs. In fact, I added both Bell and Gibbs at double-digit odds.
But if you don't have the ability to get longer numbers on those drivers or want to have extra exposure to names like Chase Briscoe, Denny Hamlin and Bubba Wallace, grabbing Top Toyota could be the move. The flexibility especially if things get wonky feels nice. If you grabbed a couple of Yotas like Bell and Gibbs or Reddick and Gibbs, I would suggest just adding the other option(s) that you feel like have a real shot. For me it's clearly Bell, Reddick, and Gibbs. Briscoe is a clear tier down but his odds are long enough where it's a fine add to the card.
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Final Betting Cards
Brian Betting Card
Kyle’s Betting Card
Good luck on all your Grant Park 165 Bets and may your DFS Lineups cash! As a reminder, only bet what you can afford to lose, especially this week. If you think you may have a gambling problem, please call 1-800-Gambler.
Both Brian and Kyle are always on the hunt for opportunities. Make sure you follow both of us on Twitter to see if we make any additional adds to the betting card. Hopefully we get some fun racing and cash some tickets in the process. Enjoy this weeks race in Chicago!