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Fantasy NASCAR Picks for the 2025 Grant Park 165: Elite Road Drivers, Sleepers & Full-On Chicago Strategy

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This Sunday’s Grant Park 165 is the only street race on the Cup Series calendar — and you know what that means: time to shake up your picks. Strategy? Crucial. Track position? Essential. Ability to survive a demolition derby dressed up as a race? Mandatory.

If you’re chasing points in your pool, this is your opportunity to outwit the field with a roster built on street-course swagger and risk-reward potential.

Let’s take a moment to appreciate the beautiful, chaotic madness that is NASCAR racing through the heart of downtown Chicago.

That’s right — it’s street course weekend, baby. Concrete canyons, 90-degree corners, and zero forgiveness. One bad braking point, and your fantasy dreams might just be pancaked against a barricade.

Let’s dive into this week’s top picks.

Top Tier Talent: Street Circuit Stars You Can’t Ignore

Before you fill out that fantasy sheet, let’s talk about the three drivers who should be locked into your lineup. These aren’t just names — they’re proven weapons in road-course warfare, armed with sharp reflexes and the confidence to brake late and dance around downtown Chicago with precision.

Tyler Reddick (#45) – Still My Ride-or-Die

I say it every week, and I mean it every week — Reddick is my mainstay. And at Chicago, I feel good about it. Last year, he started from the pole and led 8 laps before getting shuffled late. This year, with more street-course experience under his belt and Toyota’s road-course program showing strength, he’s primed to convert clean restarts into stage points.

He’s currently 6th in the standings and has quietly put together a solid road course resume with 4 top 10s in his last 6 turns-heavy starts. Watch for him to stay clean and capitalize late.

Chase Elliott (#9) – Mr. Road Course

If this were a wine tasting, Chase would be the aged cabernet of road racing — dependable, smooth, and classy under pressure. With 7 career road course wins, he’s still the Cup Series’ active leader in left-and-right-turn excellence.

He’s surging at the right time too, up to 2nd in points and carrying momentum after a top 5 at Sonoma and a runner-up at Nashville. At Chicago, Elliott’s calm approach and late-race awareness could be gold for fantasy players looking for maximum stage-point return.

Kyle Larson (#5) – The Street Hustler

Larson is that guy who can win anywhere — dirt, ovals, road courses, airport runways if you let him. He qualified on the front row here last year and ran top 3 before an unfortunate meeting with the barriers. This year, he leads the Cup Series in laps led (851) and has 3 wins, and he’s consistently delivering in fantasy scoring across all formats.

Expect him to qualify up front, score major stage points, and flirt with the win if chaos breaks his way.

Underdog Uprising: Drivers Outside the Top 12 Who Could Shock Chicago

Let’s face it, in a street race like Chicago, the “underdogs” are only one smart pit cycle away from being heroes.

Here are three guys currently outside the top 12 in points who have the street skills to vault your lineup into the winner’s circle.

AJ Allmendinger (#16) – The Street Surgeon

Every fantasy manager’s favorite road-course ringer is back and while AJ’s full-time results haven’t turned heads, his technical precision on these courses is elite.

He finished top 10 last year in Chicago, and Kaulig’s focus on short-run speed gives him a shot at grabbing stage points. Don’t be surprised if he stays in the mix all day and crosses the line top 8.

Michael McDowell (#71) – The Quiet Contender

Don’t sleep on McDowell. This guy is a legitimate road-course tactician. He was 7th in Chicago last year, has a win at Indy’s road course, and generally keeps his nose clean while others crumble. He’s had 10 top-20 finishes this season and knows how to avoid drama in the chaos.

For fantasy players who want a low-ownership, high-upside swing, this is your guy.

Shane van Gisbergen (#88) – The Street-Wise Assassin

Let’s not overthink this. Shane came into NASCAR last year with a V8 Supercar background and immediately torched the field in Chicago. He’s the defending champ here. Let me repeat that: he won this exact race last year in his Cup debut.

He’s been logging part-time starts and remains a wildcard, but his comfort level on temporary circuits is unmatched. If your pool allows it, he’s an absolute hammer pick.

Top 3 Fantasy NASCAR Picks – Grant Park 165

Ready to rule the concrete jungle? For this week’s only street race on the NASCAR calendar, I’ve locked in my top three fantasy picks who know how to tango with tight corners and concrete walls. Let’s break down the elite performers who are poised to score you big on stage points and top 5 finishes.

Driver Car # Team Wins Top 10s Laps Led
Tyler Reddick 45 Toyota 0 6 112
Chase Elliott 9 Chevrolet 1 10 136
Kyle Larson 5 Chevrolet 3 12 851

Underdog Fantasy Picks – Outside the Top 12

Want to shake up your league standings? These three picks are flying under the radar but thrive on road and street courses. If you're playing the long game, these underdogs might just help you steal the show in the Windy City.

Driver Car # Team Wins Top 10s Laps Led
AJ Allmendinger 16 Chevrolet 0 4 2
Michael McDowell 71 Chevrolet 0 2 43
Shane van Gisbergen 88 Chevrolet 1 2 85

Final Wrap-Up: Own Chicago, Own the Race

The Grant Park 165 isn’t just a race—it’s an urban obstacle course. Concrete walls are your safety net—and those who drive smart win big. My picks this week are about more than speed—they’re about surgical execution.

From Reddick’s fight last year to Elliott’s composure and SVG’s dominance, these six are the perfect combo of experience, aggression, and curb-clearing talent.

Let’s get ready for a fantasy feast—may your roster conquer the streets and avoid the walls.

See you at the finish!
—Bryan

Author Profile

Bryan
Hey there race fans, welcome to Driving on Marbles, where I break down NASCAR with real insight, smart strategy, and race by race analysis. This isn’t just race recaps and highlight talk, it’s trends, track history, driver momentum, and the little details that actually make a difference on race day.

Whether you’re setting your fantasy lineup, looking for betting angles, or just want to understand why things happen on the track, I’ve got you covered. My goal is simple: help fans see the race the way teams and strategists do, one decision, one adjustment, one edge at a time.

If you love NASCAR and want more than surface level coverage, you’re in the right place.

Let’s get you closer to the action.