The 2025 Grant Park 165 will take place on Sunday, and a side plot to the NASCAR Cup Series whipping through the streets of Chicago will be the NASCAR In-Season Challenge continuing. Ty Dillon was the last seed in the 32-driver tournament, but he bested top seed Denny Hamlin last week and now will face No. 17 seed Brad Keselowski in the Chicago Street Race. The best finisher will move on in the five-round head-to-head tournament with a $1 million prize for the eventual winner. Dillon is a +25000 longshot to win, according to the 2025 Grant Park 165 odds, while Keselowski is priced at +15000.

Meanwhile, Shane van Gisbergen, who won the 2023 Chicago Street Race, is the +150 favorite after winning on a road course in Mexico City last month. The green flag drops at 2 p.m. ET, and the race is scheduled for 75 laps around the 12-turn, 2.2-mile circuit. Before entering any 2025 Grant Park 165 picks, NASCAR DFS lineups on sites like DraftKings and FanDuel, or locking in NASCAR props on sites like PrizePicks, Sleeper Fantasy, and Underdog Fantasy, be sure to see the latest 2025 NASCAR Chicago Street Race predictions from SportsLine’s proven projection model.

Developed by daily Fantasy pro and SportsLine predictive data engineer Mike McClure, this proprietary NASCAR prediction model simulates every race 10,000 times, taking into account factors such as track history and recent results.

The model began its 2025 season by calling Chase Elliott to win for a +300 payout at the Clash at Bowman Gray and was also high on Byron as a +2000 longshot at Daytona. Then it predicted Kyle Larson’s win in Miami for a +350 payout, Christopher Bell’s +600 triumph in the NASCAR All-Star Race, Denny Hamlin’s +650 victory in Michigan, Shane van Gisbergen’s +330 victory in Mexico and Elliott’s win in Atlanta for a +1500 return. In 2024, it nailed Larson to win in Las Vegas for a 21-5 sports betting payout and predicted Denny Hamlin’s wins in Bristol at 5-1 and Richmond at 17-4.

It also impressively nailed five of Larson’s wins during his historic season in 2021. All told, the model has nailed a whopping 24 winners since 2021. Anyone who followed its lead on betting apps and sportsbooks on those NASCAR picks could have seen huge returns. New users also have the opportunity to take advantage of the latest Bet365 promo code, BetMGM promo code and Fanatics Sportsbook promo code.

Now, the model simulated the 2025 Grant Park 165 10,000 times. Head to SportsLine to see the complete projected NASCAR at Chicago leaderboard.

Top 2025 Grant Park 165 predictions

For Sunday’s 2025 Chicago Street Race, the model is high on Chris Buescher, even though he’s a +2000 longshot in the latest 2025 NASCAR at Chicago odds from FanDuel. He’s a target for anyone looking for a huge payday and first-time users can also get up to $150 in bonus bets if their first $5 bet wins with this FanDuel promo code.

After a breakout three-win season in 2023, Buescher missed the NASCAR playoffs entirely last season, but did manage to collect his sixth career victory in the NASCAR Cup Series during the postseason. He’s yet to win in 2025, but he’s in a solid position on points, as he’s sitting ninth in the NASCAR standings entering the week and has a 52-point lead over first man out Ryan Preece. However, with that bubble shrinking in each of the last three weeks, he won’t want to leave his playoff fate to chance.

Buescher has 17 career top-10 finishes in 39 starts on street courses and road courses in the NASCAR Cup Series, including a win at Watkins Glen last season. He also finished 10th in the inaugural Chicago Street Race and was top 10 in both of the road races that have taken place so far this season.

The model has also revealed a shocking NASCAR prop for Sunday: AJ Allmendinger finishes top 10 for a +120 payout. He’s potentially a strong value pick for your Chicago NASCAR prop bets.

The 43-year-old is facing a pretty significant points deficit with eight races to go in the regular season, as he’s 59 points behind current bubble boy Bubba Wallace. However, he’s an established road racer and the Chicago Street Race is a huge opportunity to make up ground. All three of Allmendinger’s NASCAR Cup Series victories have come on road courses and he’s also had nine of his 21 career top-fives and 22 of his 84 career top-10s in road races. See which other drivers to avoid and the rest of the projected NASCAR leaderboard at SportsLine.

How to make 2025 NASCAR Chicago Street Race picks

The model is also targeting two other drivers with Chicago NASCAR odds of 22-1 or longer to make a serious run at the checkered flag. Anyone who backs these drivers could hit it big. You can see all of the model’s NASCAR picks, props, and projected leaderboard over at SportsLine.

So who wins the 2025 Grant Park 165, and which longshots are must-backs? Check out the latest 2025 NASCAR at Chicago odds below, then visit SportsLine now to see the full NASCAR Chicago Street Race projected leaderboard, all from the model that has nailed 24 winners, and find out.

2025 NASCAR Chicago odds, drivers, lineup

See the full NASCAR at Chicago picks at SportsLine

(odds subject to change)

Shane Van Gisbergen +150

Tyler Reddick +750

Michael McDowell +850

Christopher Bell +1000

Ty Gibbs +1100

Kyle Larson +1500

Chase Elliott +2000

Chris Buescher +2000

William Byron +2000

Chase Briscoe +2200

Alex Bowman +2500

AJ Allmendinger +2500

Kyle Busch +3000

Carson Hocevar +3000

Ross Chastain +5000

Daniel Suarez +5000

Joey Logano +6500

Will Brown +7000

Ryan Blaney +7000

Ryan Preece +8000

Austin Cindric +10000

Todd Gilliland +13000

Brad Keselowski +15000

Denny Hamlin +15000

Bubba Wallace +20000

Austin Dillon +25000

Zane Smith +25000

John Hunter Nemechek +25000

Justin Haley +30000

Noah Gragson +35000

Erik Jones +35000

Josh Berry +35000

Josh Bilicki +50000

Riley Herbst +50000

Ricky Stenhouse Jr. +50000

Katherine Legge +50000

Cody Ware +50000

Austin Hill +50000

Ty Dillon +50000

Cole Custer +50000