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NASCAR Fantasy Rankings: DFS Picks on DraftKings for NASCAR Cup Series Grant Park 165 at Chicago

NASCAR Fantasy Rankings: DFS Picks on DraftKings for NASCAR Cup Series Grant Park 165 at Chicago

DraftKings Fantasy Advice DFS NASCAR

Updated:

By: Pearce Dietrich

The NASCAR season is revving up and DraftKings is shifting into high gear with an assortment of fantasy NASCAR contests. Dive into the best fantasy racing picks for the NASCAR Cup Series Grant Park 165 at Chicago.

For NASCAR insight and quick DFS help, follow Pearce Dietrich (@Race4thePrize) on Twitter.

Set your DraftKings fantasy NASCAR lineups here: NAS $300K Chicago Drive [$100K to 1st] (Cup)

  1. Shane Van Gisbergen ($12,000) — No Shane, no gain. The Kiwi won in Mexico weeks ago. SVG won the inaugural Chicago Street Circuit race in 2023. He’s looking to become the first to sweep Chicago by running the Xfinity Series race on Saturday and the Cup Series race on Sunday.
  2. Kyle Larson ($10,500) — Superspeedways and street circuits are not similar. While the racing differs, Cup Series results can be parallel. It’s not unusual for both types of tracks to feature all-or-nothing finishes. Larson won two road races last season. In 2025, he finished 32nd at COTA and 36th in Mexico.
  3. Christopher Bell ($10,200) — Is there a new “king of the road” in the Cup Series? Bell won at COTA and was the runner-up in Mexico just weeks ago. Last season, Bell was the runner-up at COTA and the Roval. He won the Charlotte Roval race in 2022.
  4. Chase Elliott ($9,500) — Longtime readers of the Fantasy Rankings article — now in its 11th year of DFS Rankings — know Elliott’s story. He’s streaky and surges in the summer. The strange brew of track and Elliott’s increased confidence triggers wins. His Atlanta win lit the fuse.
  5. Tyler Reddick ($9,800) — Two seasons ago, Reddick was on top of the world, ripping off three road course wins between 2022 and 2023. He was winless on road courses in 2024 but finished runner-up at Chicago.
  6. William Byron ($10,000) — Is Byron the best road racer? Is he even the best on his team? Byron has won a road course race in each of the last two seasons. He was close at COTA (runner-up) and in the mix in Mexico (ninth).
  7. A.J. Allmendinger ($9,000) — Kaulig Racing promoted The Dinger to the Cup Series with races like Chicago in mind. A win secures a playoff spot. The Dinger has a slew of Xfinity Series road course wins and a couple in Cup.
  8. Chris Buescher ($8,600) — Blue-collar Buescher still hasn’t won a road race, but he’s added two more top-10 finishes to his record. Buescher is the delivery guy: he gets the goods to you on time. It’s nothing flashy, but dependability is special. In the last 34 road races, Buescher has 17 top-10s and 23 top-15s.
  9. Ross Chastain ($8,100) — Trackhouse Racing is the road ringer team, founded by a road course aficionado and recruiting a stable of savvy street circuit speedsters. Chastain had the second-best median finish at road courses in 2024. He won at The Circuit of The Americas in 2022.
  10. Ryan Blaney ($7,500) — The No. 12 Penske Ford has struggled only at road courses this season — 19th at COTA and 14th in Mexico. That wasn’t the case in 2024, when Blaney earned three top-10s and four top-15s.
  11. Chase Briscoe ($8,000) — His switch to JGR might reignite his road racing career. Briscoe won multiple road course races in the Xfinity Series but struggled in the Cup Series with SHR. His JGR tenure began with a 14th-place finish at COTA and a top-10 finish in Mexico.
  12. Michael McDowell ($8,300) — His switch from Front Row Motorsports to Spire hasn’t affected his road course program. The longtime underdog road ringer finished 11th at COTA and fifth in Mexico.
  13. Kyle Busch ($7,700) — Victory Lane is likely not the destination for the RCR driver on Sunday. Those days are done for the veteran driver. At his price, he’s still in play in DFS. Busch had top-15 finishes in all five 2024 road races and finished fifth at COTA earlier this season.
  14. Alex Bowman ($8,800) — Hendrick’s worst road racer is better than 90% of the field. Bowman won the 2024 Grant Park 165 at Chicago. It was a wonky win, but many road races are. Bowman never looks pretty, but he consistently records top-10 finishes — two in 2025, two in 2024, and three in 2023.
  15. Austin Cindric ($7,800) — The road race ace hasn’t forgotten how to road race; everyone else has caught up. It’s one thing to dominate the Xfinity Series, but the Cup Series is filled with elite drivers. Cindric’s struggles have suppressed his salary, making this a buy-low opportunity.

Pearce Dietrich

I am a promoter at DraftKings and am also an avid fan and user and may sometimes play on my personal account in the games that I offer advice on. Although I have expressed my personal view on the games and strategies above, they do not necessarily reflect the view(s) of DraftKings and do not constitute a representation that any particular strategy will guarantee success. All customers should use their own skills and judgment in building lineups. I may also deploy different players and strategies than what I recommend above. I am not an employee of DraftKings and do not have access to any non-public information.