The Chicago Street Race has quickly become one of the most thrilling visual spectacles in the NASCAR Cup Series and the 2025 Grant Park 165 will also serve as the second round of the first-ever NASCAR In-Season Challenge. Shane van Gisbergen won the first Cup race on the Chicago Street Course in 2023 and the road-racing specialist, who claimed the pole on Saturday, is the +150 favorite in the 2025 Grant Park 165 odds after winning three weeks ago in Mexico City. Van Gisbergen will start on the pole for Sunday's Grant Park 165 after posting a lap at 89.656 seconds. 

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 winding through the streets of Chicago. Before making any 2025 NASCAR Chicago Street Race predictions, you NEED to see the latest 2025 Grant Park 165 picks from SportsLine's proven projection model.

Our proven projection model has simulated Sunday's 2025 Grant Park 165 10,000 times and come up with a surprising leaderboard. Developed by daily Fantasy pro and SportsLine predictive data engineer Mike McClure, this proprietary NASCAR prediction model takes into account a slew of factors, including track history and recent results.

McClure's model began the 2025 season by calling Chase Elliott's win in the Cook Out Clash at Bowman Gray for a +300 payout. Then at Daytona, it was also high on William Byron despite +2000 odds and it went on to predict Kyle Larson as a +350 winner in Miami, Christopher Bell as a +600 winner in the NASCAR All-Star Race, Denny Hamlin for a +650 payout in Michigan, Shane van Gisbergen's win in Mexico City for a +330 score and then Elliott for a +1500 payout in Atlanta. The model also called its first victory of the 2024 season with Larson winning in Las Vegas for a 21-5 payout then predicted Denny Hamlin's wins in Bristol at 5-1 and Richmond at 17-4. 

It impressively nailed five of Larson's wins during his historic season in 2021 too. All told, the model has nailed a whopping 24 winners since 2021 and has hit five winners already in 2025! Anyone who followed its lead on those NASCAR picks could have seen HUGE returns.

Now, the model has dialed in on NASCAR at Chicago 2025 and released its projections.

For Sunday's 2025 Grant Park 165, we can tell you the model is high on Chris Buescher, even though he's a longshot at +2000 in the latest 2025 NASCAR at Chicago odds. He's a target for anyone looking for a HUGE payday. It's also revealed a shocking NASCAR prop for Sunday: AJ Allmendinger finishes top 10 for a +120 payout. He's a potentially a strong value pick for your Chicago NASCAR prop bets.

The model is also targeting TWO OTHER drivers with 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 ABSOLUTELY NEED to see who they are before locking in any NASCAR picks.

So who wins the 2025 Grant Park 165, and which EPIC longshots are MUST-BACKS? ... Join SportsLine right now to see the full projected NASCAR at Chicago leaderboard, all from the model that's nailed 24 winners!