The NASCAR Cup Series roars into the heart of the Windy City, where steel and glass scrape the sky and the streets themselves become the stage.
From the mirrored curve of The Bean to the riverside shimmer of the Riverwalk, the city pulses with energy. The skyline stands sentinel as engines echo beneath the storied towers, and the roar of the crowd mingles with the hum of Lake Michigan just beyond Grant Park.
Although rain threatens to disrupt the action that is scheduled to take place at 2:00 p.m. ET this Sunday on TNT, my NASCAR race picks believe no matter when they race, Chase Elliott is once again going to be a problem for the short-priced favorite and former Chicago street race winner in Shane van Gisbergen.
Discover exactly why I'm once again touting the second-generation driver, and get the rest of my free betting picks below.
NASCAR prop picks for Grant Park 165
- Top 3 Finish: Chase Elliott (+400)
- Top 5 Finish: Tyler Reddick (+220)
- Ross Chastain (+100) over AJ Allmendinger
NASCAR Grant Park 165 props and best bets
Top 3 Finish: Chase Elliott (+400 at bet365)
Have you ever heard the old cliche, when a guy has got, he's got it? It gets thrown around by a lot a run of run-of-the-mill sports betting pundits, myself included. But, my friend, Chase Elliott has got it going for him to the nth degree.
Yes, if it wasn't for a little bit of that "Shake N' Bake" action from Elliott's Hendrick Motorsports teammate, Alex Bowman, last week in Atlanta, Elliott never would have picked up the dub. Even still, I'd be willing to bet my mortality that he would've finished in the Top 3. His car was flying.
CHASE ELLIOTT WINS IN ATLANTA! pic.twitter.com/EQfNV9JuNR
— FOX: NASCAR (@NASCARONFOX) June 29, 2025
Elliott earned an impressive Top 3 finish at the Mexico City road course and a fourth at Circuit of the Americas — both incredibly technical layouts that demand precision and racecraft.
On top of that, his overall 2025 stats are strong, with 5 Top 5s and 9 Top 10s in 17 starts. Elliott’s consistency is no fluke; he’s finished in the Top 5 in nearly a third of his races since 2023, and his ability to avoid trouble is reflected in his zero DNFs this season.
Let's not forget that Elliott is one of NASCAR's premier road course drivers. As of mid-2025, he has recorded 17 Top 5 finishes and 27 Top 10 finishes on Cup Series road courses over his career. In fact, Elliott has seven Cup Series road course wins on his resume, the most among active drivers.
Now you're telling me I can get a guy, when push comes to shove, who can do some magical things on road courses at +400 to finish in the Top 3? Square bet or not, I'd be nuts not to take it. To me, this number is a gift, and we can all thank our favorite Cup Series driver from New Zealand for this glorious opportunity.
Top 5 Finish: Tyler Reddick (+220 at bet365)
When I saw this +220 Top 5 line on Reddick, it stopped me from scrolling. Compared to years past, Reddick hasn't been as dominant, but he's still one of the better drivers in the Cup Series today.
Reddick sits sixth in the Cup points standings and has notched four Top 5 finishes and six Top 10s, with his best result being a second-place finish in the Daytona 500. Reddick has an average finish of 14.9 and has led 112 laps this year.
Notably, he has avoided any DNFs, running 99.9% of all possible laps, and has started from the pole once.
In terms of his non-oval racing resume, Reddick has made 22 career Cup Series starts on road courses. In those races, he has earned four wins, eight Top 5 finishes, and 13 Top 10 finishes. His victories have come at Road America (2022), Indianapolis Motor Speedway Road Course (2022), and Circuit of the Americas (2023 and 2024).
Once again, with the bookies trying to protect themselves from what seems like a statistically plausible SVG win, they've left themselves vulnerable in other areas.
If Reddick can qualify well, I see no reason why he can't make it into the Top 5. I have this line projected closer to +150, so I'm happy taking what the books are giving me here with Reddick.
Ross Chastain (+100 at bet365) over AJ Allmendinger
I don't understand why this line isn't at least a pick 'em. In my books, the odds are flipped, with Chastain being the slight favorite. That's more of a gut check on my part, though.
That said, to verify or refute my instinct, I asked ChatGPT to make the case for Chastain in this head-to-head match. The bot said:
"While Chastain’s raw speed metrics this year (17th in speed, 19th in pit-crew performance) are modest, he excels in racecraft: he ranks No. 4 on restarts, No. 6 in defense, and No. 8 in passing, showing he consistently gains positions through skill rather than just equipment. His head-to-head record is unmatched — Chastain is 22-7 against his Trackhouse teammates this season and owns a 94-47 (66.7%) career Cup Series head-to-head mark since joining the team, the best in the series.
"Chastain’s ability to maximize results is clear: he has 3 Top 5s and 8 Top 10s in 2025, with an average finish of 14.44 despite not always having the fastest car. He’s shown the capacity to drive from the back to the front and adapt to changing race conditions, a skill crucial on street courses like Grant Park. In contrast, Allmendinger has struggled for consistency and doesn’t have the same level of recent Cup Series results or the proven ability to outperform his equipment and competition over a full season. Chastain’s relentless, adaptable style and proven results under pressure make him the more reliable pick to finish higher in this race."
And you know what, with even odds, I'll just go with the numbers. It'll give me something to look out for if the race gets a tad bit boring at the front of the pack. After all, everyone says this is SVG's race to lose.
Odds are correct at the time of publishing and are subject to change.
Not intended for use in MA.
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