NASCAR: 3 longshot picks to win the Chicago street race

Bubba Wallace, 23XI Racing, Chicago, NASCAR (Photo by Patrick McDermott/Getty Images)
Bubba Wallace, 23XI Racing, Chicago, NASCAR (Photo by Patrick McDermott/Getty Images) /

The long-awaited first ever NASCAR Cup Series street course race is scheduled to take place at the Chicago Street Course this Sunday.

For the first time ever, the NASCAR Cup Series is set to run a street race this coming Sunday in Chicago, Illinois.

There had been talk of a potential street race for quite some time, and rumors emerged that the Windy City could play host after a virtual race was contested in Chicago on iRacing two summers ago. That rumor ultimately came to fruition, with the inaugural Grant Park 220 announced as a part of the 2023 schedule last summer.

This 100-lap race around the 12-turn, 2.2-mile (3.541-kilometer) temporary street course, which is officially named the Chicago Street Course, has all the makings to be a crazy one which could shake up the playoff picture.

It is the 18th race on the schedule, marking the halfway point of the season, and there will be just eight regular season races remaining on the calendar once it concludes.

We know which races are typically considered “wild card” races. Superspeedway races at Daytona International Speedway, Talladega Superspeedway, and now even Atlanta Motor Speedway certainly qualify, as do a lot of the road course races. A few other oval races have that unpredictability potential as well.

But with this race being the first of its kind in the sport’s 75-year history, there has never been a bigger true “wild card” race that this one.

There are three drivers in particular whose odds at DraftKings Sportsbook, which is now offering an instant $150 to those who sign up and bet $5, don’t do justice to their chances of winning Sunday’s race.

NASCAR at Chicago: Grant Park 220 longshot picks – Denny Hamlin

Joe Gibbs Racing’s Denny Hamlin has just one career road course win, but his four career road course poles, including one in the most recent race at Sonoma Raceway, show that he has had the speed to contend on tracks with both left and right turns.

You also simply aren’t ever going to get +3500 odds on Hamlin in any other race, and Toyota’s road course resurgence is real. They are two for two to start the season, with 23XI Racing’s Tyler Reddick winning at Circuit of the Americas and Joe Gibbs Racing’s Martin Truex Jr. winning at Sonoma Raceway.

NASCAR at Chicago: Grant Park 220 longshot picks – Michael McDowell

Front Row Motorsports’ Michael McDowell has become a serious contender in road course races in recent years, specifically since the introduction of the Next Gen car a year ago. He has scored five top eight finishes in the last seven road course races. He has qualified well as well, securing five top seven starts during that span.

Considering how he hit the ground running in road course events with the new car, expect him to hit the ground running in the new street course event. His +2800 odds make him an attractive upset pick.

NASCAR at Chicago: Grant Park 220 longshot picks – Chris Buescher

RFK Racing’s Chris Buescher has quietly emerged as one of the top road course racers in the Cup Series, so the fact that he is only listed at +2500 makes him somewhat overlooked. He too has been a regular contender in these races since the introduction of the Next Gen car, having recorded six top 10 finishes in the last seven road course races.

If he continues to run well, you have to believe that he is going to find victory lane sooner rather than later, especially amid the resurgence of RFK Racing this season.

Next. All-time NASCAR Cup Series wins list. dark

NBC is scheduled to broadcast the Grant Park 220 live from the new Chicago Street Course beginning at 5:30 p.m. ET on Sunday, July 2. Be sure to take advantage of FuboTV’s free trial offer today and don’t miss it!