The Cup Series is wading into unknown territory this weekend as NASCAR races on a street circuit for the first time in its history.

The site of this historic event: the streets of Chicago.

NASCAR returns to the Chicago area for the first time since 2019, last racing in nearby Joliet, Illinois, at the 1.5-mile Chicagoland Speedway.

Should this weekend be a success for NASCAR, it opens significant possibilities to race in major cities without purpose-built race tracks. Sunday’s race marks not only a notable new race on the Cup Series calendar but the potential start of a new era in NASCAR.

The challenges presented by the street circuit in Chicago are unlike any we’ve seen before. With tight, 90-degree corners and no margin for error with minimal run-off area, it’ll be a test for drivers to even make it to the checkered flag.

Here are four drivers that could win the first-ever street course race in Cup Series history.

Chase Elliott

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Simply put, when the Cup Series goes to a road course, Elliott is a contender to win.

The pressure is on for Elliott to pick up his first checkered flag of the campaign, too. After missing seven races due to an injury and a suspension, the driver of the No. 9 Chevrolet is 64 points out of the final playoff spot. Should anyone below the cutline win one of the final nine races of the regular season, that gap would increase.

Elliott could still point his way into a postseason position. But with three road courses on the remaining regular-season schedule, beginning this weekend on the streets of Chicago, he has a strong chance to lock himself in with a win.

The 27-year-old has dominated when NASCAR has gone to new road courses in recent years. He won the inaugural Cup Series races at Circuit of the Americas, the Daytona road course, and Road America, and finished fourth at the Indianapolis road course.

All signs point to Elliott being a serious threat at Chicago.

A.J. Allmendinger

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Allmendinger hasn’t quite been the contender on road courses in 2023 as was anticipated, but don’t let that get you down on him heading into the weekend.

The 41-year-old is among the most experienced road course racers in the Cup Series. He’s dominated in the Xfinity Series and captured the inaugural win on the road course at Indianapolis in 2021 as a part-timer.

If Kaulig Racing is to make the Cup Series playoffs for the first time, it’ll likely have to come on the back of an Allmendinger win at a road course. Going to a challenging, new circuit with no margin for error, Allmendinger’s experience and prowess on this track type will surely make him among the favorites on Sunday.

Tyler Reddick

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Toyota’s had a resurgence on road courses early in 2023. The addition of Reddick has clearly paid dividends quickly, with the 23XI driver capturing the first road course win of the campaign at Circuit of the Americas.

Whatever road course knowledge Reddick brought to the table was dispersed by Sonoma, as Martin Truex Jr. and Denny Hamlin combined to lead 84 of 110 laps for Toyota.

Since the start of 2022, Reddick has been the most consistent contender for race wins at road courses. He’s gone to victory lane three times – at Road America, Indianapolis, and COTA – and has qualified in the top five in all eight road course races in that span.

His 120 laps led over those eight races is second only to Chase Elliott, and his 250 total points earned trail only Chris Buescher.

Avoiding the inevitable chaos will be a major key to victory for whoever wins on Sunday, and starting at the front is a good way to do so. Nobody has done so as regularly as Reddick, giving him a strong shot to win this weekend.

Shane van Gisbergen

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Van Gisbergen is the latest driver to get behind the wheel in Trackhouse’s Project 91 car, and he immediately becomes a legitimate threat to win this weekend in Chicago.

Kimi Raikkonen – the previous driver of Trackhouse’s third entry – is a far more recognizable name to racing fans worldwide. After all, he’s a Formula 1 champion, a 21-time Grand Prix winner, and a fan-favorite personality. But he’s also past his prime in his early 40s and comes from an open-wheel background.

Van Gisbergen, on the other hand, is in the prime of his career and comes from the Australian Supercars series. Driving heavy touring cars on a variety of difficult circuits, including multiple street courses, van Gisbergen has a wealth of experience driving comparable cars on this type of track.

Marcos Ambrose was a perennial contender on road courses in the Cup Series after a career in the Supercars series. Van Gisbergen will look to carry the torch in his NASCAR debut – and don’t be surprised if he makes a major impact right away.

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