Sunday's Grant Park 165 on the streets of Chicago will be the site of the second round of NASCAR's In-Season Challenge, which saw multiple upsets shake up the bracket following a chaotic first-round race at EchoPark Speedway (formerly Atlanta Motor Speedway).
While Chase Elliott got around Brad Keselowski with a last-lap pass to win at his home track and advance to the second round of the challenge, some of the other top seeds were not as fortunate. Top seed Denny Hamlin was caught up in the Lap 69 Big One and eliminated by No. 32 seed Ty Dillon, while No. 2 seed Chase Briscoe, No. 4 seed Christopher Bell, No. 7 seed Ryan Blaney and No. 10 seed Kyle Larson were all eliminated.
That sets the stage for some underdog stories to emerge, beginning with the Chicago Street Race this weekend. The Cup Series has only made two trips to the streets of Chicago and dealt with weather both times. Some drivers are excellent on road and street courses, while others have been solid enough to capitalize if the unpredictability transfers over from EchoPark Speedway.
Here are three drivers that could surprise on Sunday and advance to the quarterfinal round of the In-Season Challenge.
AJ Allmendinger, No. 16 (Kaulig Racing Chevrolet)
The veteran Allmendinger has been consistent all season and stayed around the playoff bubble for much of the 2025 campaign. His four top-10s have come on 1.5-mile tracks (Las Vegas, Homestead-Miami, Charlotte) and the half-mile Bristol Motor Speedway, but his expertise is on road and street courses. He has not finished better than 17th in his two starts in Chicago, but has three road course wins and seems to always be a factor on those layouts.
The No. 22 seed Allmendinger finished a solid 12th at EchoPark Speedway to eliminate the No. 11 seed Michael McDowell, who was 18th. He is pitted against the sixth seed Ty Gibbs, who outran the No. 27 seed Justin Haley to advance.
This will not be an easy matchup though, considering Gibbs has finished top 10 in both Chicago Street races and had one of the fastest cars at the most recent road course in Mexico City. It should create an exciting matchup and potentially another upset, although Allmendinger's road racing background is as strong as anyone in the field.
Zane Smith, No. 38 (Front Row Motorsports Ford)
The 26-year-old driver for Front Row Motorsports has had a quiet season and finished inside the top 10 in two of the last four races at Michigan (seventh) and EchoPark (seventh). He has not been great on the two road courses this season with a best finish of 29th at COTA, but he was a respectable 17th at Chicago last season and has five top-20 finishes in nine Cup Series starts on road courses, including a fifth-place finish at Watkins Glen in 2024.
The No. 14-seed's seventh-place finish was enough to eliminate No. 19 seed Austin Cindric, who was caught up in the Big One at EchoPark and finished 38th. Smith's second-round opponent is the No. 3 seed Chris Buescher, who defeated the 30th seed Todd Gilliland in the first round.
Buescher is a past winner at Watkins Glen (2024) and has finished top 10 in both road course races this season. His best finish at Chicago is 10th in 2023. Smith will likely have to finish inside the top 10 if he is going to have a shot, but with the chaos the streets of Chicago have produced so far, don't count the two-time Truck Series road course winner out on Sunday.
Carson Hocevar, No. 77 (Spire Motorsports Chevrolet)
Hocevar has been one of the fastest drivers all season, including Saturday night's race at EchoPark Speedway when he drove his way through the field multiple times. He finished 10th, which was more than enough to take down No. 7 seed Ryan Blaney, who came home last in the 40-car field after getting collected in the first multi-car wreck on Lap 57. Hocevar has limited experience on road courses, but has three top-15 finishes, including a third at Watkins Glen in 2024.
The No. 26 seed will square off with the 23rd seed Tyler Reddick, who eliminated the 10th seed Kyle Larson. While the seeding is similar between the two drivers, Reddick has the upper hand with a runner-up at Chicago last season and three road course wins.
This is a difficult matchup for Hocevar, but he has showed how competitive he can be on multiple track types. Why should Sunday's race on the streets of Chicago be any different?