DraftKings NASCAR DFS Picks for Chicago: Fantasy NASCAR Strategy and Picks for the Grant Park 220

Street-course racing take center stage this weekend for the NASCAR Cup Series.

Parts of downtown Chicago have been converted into a 2.2-mile racetrack with 12 turns that’s sure to produce high drama.

Drivers were able to take part in a 50-minute practice session, but there was little-to-no indication of how racing would play out with the Next Gen cars on this tight street course.

In another twist, there is potential for some lingering rain in the forecast.

As such, with such high uncertainty surrounding this race, we need to plan accordingly when setting our DFS lineups.

Before we jump into my picks, don’t forget all my NASCAR projections can be found in the NASCAR Models on FantasyLabs, complete with floor, ceiling, median, and ownership projections.

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.

Here are my NASCAR DFS picks for Sunday’s Grant Park 220 at Chicago.

Chicago DraftKings DFS Cash Game Picks

Denny Hamlin ($8000): Despite the uncertainty, the safest place to be is at the front, especially at a tight road course that may be difficult to pass at. The discounted price that Hamlin has is also nice, as it makes every lap led and fastest lap more meaningful than if he was over $10k.

Hamlin was clearly one of the cars to beat in practice, posting the second-best single lap time. He also had the best five- and 10-lap average speeds in the session. After a great showing at Sonoma, it’s clear Toyota is back at road courses.

Austin Cindric ($8400): The second-year driver starts 31st after a practice incident where he tagged the wall set him behind.

However, prior to that incident, Cindric had posted top-10 times in the session on his first stint, showing how quickly he got up to speed. Thankfully for him there are 220 miles to continue to get up to speed and learn the track. I fully expect by the middle to end of the race, he’ll be posting competitive lap times with the top third of the field.

It’s too hard to pass on the road-course ace who showed early practice speed, starts 31st and comes in at a middling salary.

I like him in tournaments as well, especially if people are scared off by his lack of practice speed, which isn’t taking into account the full context of drivers improving over the 50-minute session.

Ross Chastain ($9600): With so much uncertainty, we have to rely on safety to lead the way in cash-game lineups, so we’re continuing to stack the back with drivers who qualified poorly but are generally in good equipment and good at road courses.

Chastain clearly fits that bill, as the three-time Cup Series winner has one of his wins at a road course.

Chastain is no stranger to aggression, and with the potential for mayhem, look for him to take advantage of any situation he can to move forward.

Chicago DraftKings DFS Tournament Picks

William Byron ($9400): Track position is going to be huge, and there’s no better way to get track position than through a stellar pit crew. Byron has easily had the best pit crew in 2023, and with the potential for plenty of cautions, that could mean a handful of opportunities to take advantage of the best crew in the business.

Byron also shot out to an early top-10 practice time prior to his own contact with the wall about one-third of the way through the session, setting him back. But like Cindric, Byron should be able to make his way forward throughout the race as they make improvements and he better learns the track.

Ty Gibbs ($7300): My model has Gibbs as the second-most likely driver to exceed his usage projection when it comes to the chances he ends up in the optimal lineup, after only Austin Dillon.

Gibbs spent plenty of time in the simulator getting ready for this track, and it showed as he got up to speed quite quickly after sitting out most of the early portion of practice.

In fact, Gibbs only turned 15 laps in practice, which was the fewest of any driver inside the top 11, showing how it didn’t take him long to find top-10 pace.

Noah Gragson ($5300): Gragson showed some impressive speed in practice, leapfrogging several drivers late to end up 12th in the lone practice session.

The rookie driver has had a difficult year, and he isn’t known as a road-course ace, which should limit others’ exposure to him. But in a race with the chance for chaos, as long as he survives and posts speeds anywhere near where he ended up in practice, he’ll be a good bet to move up from his 23rd-place starting position.