Martin Truex Jr. has five career road-course victories, including four at Sonoma. 

This weekend, NASCAR will make history, as the Cup Series will race through the streets of a major city.

For the first time ever, the NASCAR Cup Series will rip through downtown Chicago, along Lake Shore Drive, Michigan Avenue, Columbus Drive … through Grant Park and toward Soldier Field in the Grant Park 220, which will be held Sunday evening in the Windy City (5:30 p.m. NBC).

The 12-turn, 2.2-mile Chicago Street Race will be the 177th different "track" the NASCAR Cup Series has competed on in its 75-year history.

This will be the second time NASCAR has competed in downtown Chicago, racing at Soldier Field in 1956.

As far as road courses go, this will be a first for even the most experience road-racer.

“I think it’s a good idea, I’ve just never done street racing before,” said Martin Truex Jr., who leads the Cup Series in points and also won the last road race of the season at Sonoma, which was his fourth career victory at the California track. “I have no idea the logistics involved. I can’t even imagine what goes into it.

“I enjoy tracks that are unique and challenging and it’s always a good challenge to learn a new place.”

Truex has five career road-course victories, which is second-best among active Cup drivers. Chase Elliott has the most out of any current driver with seven. The driver of the No. 9 Hendrick Motorsports Chevrolet is the favorite this weekend in Chicago, sitting at +500 to take the checkered flag.

However, Elliott is winless in a season where he’s also missed seven races.

FrontPageBets takes a look at drivers to watch in the first-ever Chicago Street Race.

(All odds courtesy of Caesars and are subject to change)

Pick to win: Martin Truex Jr. (+700)

With no one knowing what to expect in this first-time event, experience can make all the difference.

And Truex has it.

Sunday’s race will be the 43-year-old veteran driver’s 639th career Cup start; and his 48th on a road course. Truex has won five of them, while also racking up 22 top-10 and 14 top-5 finishes.

He’s three weeks removed from his fourth Sonoma victory and took second last week in Nashville.

Along with his two wins this season, Truex also has nine top-10s. He leads the Cup point standings by 18 points over William Bryon and Ross Chastain.

Sports betting odds explained

Top-3 pick: Tyler Reddick (+225)

Three of Tyler Reddick’s four Cup Series wins have come on road courses, including this season at the Circuit of the Americas.

In 17 career road-course starts, Reddick has 10 top-10 finishes, including five top-5s.

The driver of the No. 45 23XI Racing Toyota is 13th in Cup points and has five top-5s this season.

Top-10 pick: Chase Elliott (-250)

Seven of Elliott’s 18 career wins have come at road courses, as he, again, leads all active drivers in victories on those tracks.

Elliott also has 18 top-10 finishes in 26 career road-course starts.

While he missed six races after breaking his leg and another one because of a suspension, Elliott has finished in the top 10 in six of his 10 starts this season.

Odds-on favorites to win Chicago’s Grant Park 220

Chase Elliott +500

Tyler Reddick +650

Martin Truex Jr. +700

Kyle Larson +700

Ross Chastain +1000

A.J. Allmendinger +1000

Kyle Busch +1200

William Byron +1500

Chris Buescher +2000

Christopher Bell +2000


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Mike Szvetitz is the General Manager and Content Director for FrontPageBets.com. Szvetitz is a 23-year veteran reporter and editor, including serving 17 years as a sports editor in Florida, Alabama and Virginia, covering everything from preps to pros. His "View From The Lazy Boy" column won multiple state and national awards. He can be reached at mszvetitz@timesdispatch.com.