NASCAR Predictions for Chicago Street Race 2025: Grant Park 165 Odds, Prop Bets & Expert Picks

After Brad Keselowski came this close to cashing our 16-1 ticket last week, the NASCAR Cup Series heads to the Chicago Street Course for the 2025 Grant Park 165. We’ll dive into the latest odds across the best sports betting sites for our best NASCAR predictions to win the Chicago Street Race, as well as our NASCAR prop bets at Chicago.

📊 Grant Park 165 odds & betting lines: Chicago Street Race 2025

Here are the latest Grant Park 165 odds and favorites for the Chicago Street Race via BetMGM as of Friday.

🥇 Chicago Street Race betting favorites 🥇

• Shane van Gisbergen, +200 ($10 to win $20)
• Christopher Bell, +725 ($10 to win $72.50)
• Kyle Larson, +750 ($10 to win $75)
• Chase Elliott, +1100 ($10 to win $110)
• Ty Gibbs, +1100 ($10 to win $110)
• Tyler Reddick, +1100 ($10 to win $110)
• Alex Bowman, +1800 ($10 to win $180)
• William Byron, +1800 ($10 to win $180)
• Chris Buescher, +2000 ($10 to win $200)
• Michael McDowell, +2500 ($10 to win $250)
• AJ Allmendinger, +2500 ($10 to win $250)

Claim our BetMGM bonus code, SBRBONUS, to receive up to $1,500 in bonus bets by placing a wager of any amount on the Grant Park 165 or any other market!

🏁 Chicago Street Race predictions, expert picks & best bets

Whenever you see a NASCAR Cup Series driver with odds of +200 or shorter to win a race, you know they’re not the play. They may win the race, but that $20 return on a $10 bet isn’t worth the implied probability (33.3%), especially not in a 40-car field, and especially not with variance-inducing rain in the forecast.

Shane Van Gisbergen may be the best road course driver in the field, and his dominant win in Mexico City proved that his No. 88 Chevrolet has the speed necessary to win, but that doesn’t justify the price. We’ll be looking further down the oddsboard for this weekend’s event.

While there are no other street circuits on the NASCAR schedule, Chicago Street compares more favorably to dual-purpose venues (think the Charlotte Roval) than traditional road courses. As a result, I predict A.J. Allmendinger will win the Grant Park 165.

🏆 Pick to win Grant Park 165

✅ Prediction: A.J. Allmendinger ⭐⭐⭐⭐
📊 Best odds: +2500 via ESPN BET ($10 to win $250)

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It’s been a rough few years for Allmendinger with Kaulig Racing, but the team has seemingly turned the corner this year. Allmendinger is already up to four top 10s, and he would have five but for a disaster in the closing laps at the Circuit of the Americas.

No Cup Series regular has as impressive a resume as Allmendinger does at venues like this one. In addition to four wins in five Xfinity Series starts at the Charlotte Roval, Allmendinger has Cup Series victories at the Charlotte Roval and the Indy Road Course.

His two Cup Series starts at the Chicago Street Course haven’t gone well, but with the No. 16 team bringing more speed than we’ve seen of late to both COTA and Mexico City, I’m optimistic about Allmendinger in what’s close to a do-or-die position to keep his playoff hopes alive.

A simple $10 bet will score you a massive $250 payday if Allmendinger pulls this off - far better than the peanuts you’d get from betting on SVG.

💎 Best value bet to win Grant Park 165

✅ Prediction: Chris Buescher ⭐⭐⭐⭐
📊 Best odds: +2500 via ESPN BET ($10 to win $250)

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Both Allmendinger and Chris Buescher clock in at odds of +2500 at ESPN BET, but you won’t find them at that price anywhere else. They should be in the +1800 to +2200 range. While Buescher doesn’t have quite the resume that Allmendinger does, he has won on a road course more recently. He took home the checkered flag at Watkins Glen last season.

Also unlike Allmendinger, Buescher is one of four drivers on the entry list to rank in the top 10 by average green flag speed in both races at the Chicago Street Course to date. He clocked in at ninth last year after clocking in at 10th in 2023. That didn’t translate to race-winning speed, but sometimes all you need is a competitive car and a little bit of luck.

While Buescher has a shot to get into the playoffs based purely upon points, his recent soundbites indicate he feels he needs to win to lock down his spot. With 11 different winners so far this year, Buescher’s comments seem more prescient by the day. Don’t be surprised if his crew makes an aggressive call late, allowing him to edge out SVG like he did at the Glen last year.

🎯 Best long shot to win Grant Park 165

✅ Prediction: Todd Gilliland ⭐⭐⭐
📊 Best odds: +15000 via ESPN BET ($10 to win $1,500)

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With weather possibly in the forecast, Allmendinger (who has multiple wet-weather wins) stands out, but so does Todd Gilliland. He scored an impressive Truck Series win at COTA in 2022 despite terrible conditions. He also impressed early at a soggy Watkins Glen race later that year.

Gilliland doesn’t have a road-course win to his name in the Cup Series, but Front Row Motorsports and Gilliland’s No. 34 team have a strong notebook for these circuits thanks to Michael McDowell’s tenure.

It’s a true long shot, but Gilliland could just come in at +15000, delivering a $1,500 return on a $10 wager in the process.

💰 Best NASCAR prop bets at Chicago

We’ll be revisiting some of the drivers discussed above for our Grant Park 165 prop bets, as the best sports betting apps continue to underestimate the inevitability of Buescher finding his way into the top 10 at a road course.

🔥 Best prop bet for Grant Park 165

✅ Prediction: Chris Buescher top 10 ⭐⭐⭐⭐⭐
📊 Best odds: +140 via Hard Rock Bet ($10 to win $14)

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When I hear “this bet has hit in X of the last Y,” I tend to tune that out as noise, but there’s a clear signal with Buescher. He's scored a top-10 finish in 10 of the last 13 road course races (76.9%). Despite his success, he is still +140 (41.7%) at Hard Rock Bet to score a top 10 this weekend. If that book isn’t available in your state, he is +125 (44.4%) at ESPN BET to do so.

The range on this play is quite wide, as Caesars (-130) and DraftKings (-110) have Buescher at odds well below +100 (50%), and rightfully so. This wager is one of those that you should take whenever it’s available at plus-money because you’ll likely end up in the black on it once the season ends, even if it doesn’t hit every time.

🚀 Best long-shot prop bet for Grant Park 165

✅ Prediction: Todd Gilliland top 10 ⭐⭐⭐
📊 Best odds: +600 via Hard Rock Bet ($10 to win $60)

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Getting Gilliland at this price is a huge win for us. The pilot of the No. 34 Ford clocks in at +350 on BetMGM and +450 on DraftKings, so we’re getting a steal relative to more efficient books.

While Gilliland is yet to find Victory Lane on a road course in the Cup Series, he has scored five such results on road courses in 19 starts. That includes three of his seven starts since 2024 and the most recent Chicago Street race.

📈 Grant Park 165 trends & Chicago Street Race history

Here are a few Grant Park 165 trends to consider before betting on the Chicago Street Race on Sunday.

🏎️ Start up front, finish up front. While stage breaks make starting position less important at road courses than it used to be, the Chicago Street Course is yet to see a winner who started from outside the front four rows. Shane Van Gisbergen just won at Mexico City after starting on the pole a few weeks ago, too.

🏎️ Win the first stage, lose the race. Stage breaks can make road course strategy quite interesting as certain drivers opt to punt the optimal strategy for stage points. As a result, the Stage 1 winner in both road course races this year finished outside the top 10. Neither Stage 1 winner at Chicago Street won the race, either.

💡 How to bet on NASCAR: Chicago Street Race

When betting on road courses, especially those for which rain may be a factor, these NASCAR betting strategy tips may come in helpful:

• Don’t overpay for the big favorite. While road courses have often been dominated by specific drivers (Chase Elliott’s run comes to mind), that doesn’t mean large favorites are profitable over the long run. Remember that it’s a 36-to-40-car field before laying more than 10% (or 20% ... or 30%) for one driver.
• Don’t let performance on ovals influence you. Some drivers do well on road courses, while others do not. There’s a reason why Denny Hamlin, who is often atop the odds board on ovals, is a long shot for this weekend’s race; conversely, there’s a reason why Shane Van Gisbergen, who is often far down the board on ovals, is at the top.
• Do some research on who drives well in the rain. Drivers from open wheel, sports car, or Australian supercar backgrounds tend to have far more experience in wet-weather conditions than guys who cut their teeth racing on ovals, where racing in the rain is often too dangerous to perform.

🏆 Past Chicago Street Race winners

Here is a look at every Chicago Street Race winner entering Sunday's race.

📺 How to watch the Chicago Street Race (Grant Park 165)

📅 Race date: Sunday, July 6, 2025
🕒 Start time: 2 p.m. ET
📍 Track: Chicago Street Course (Chicago)
📺 TV: TNT | Streaming: HBO Max

❓ Grant Park 165 FAQs

Who is favored to win the Grant Park 165?

Shane Van Gisbergen is the favorite to win the 2025 Grant Park 165 with his +200 odds representing a 22.2% implied probability. If he wins, a $10 bet at those +200 odds would return a $20 profit.

What are the odds for the Grant Park 165?

Shane Van Gisbergen (+200), Christopher Bell (+725) and Kyle Larson (+750) are the favorites to win the Grant Park 165 by the latest NASCAR Cup Series odds.

What time is the 2025 Grant Park 165?

The 2025 Grant Park 165 starts at 2 p.m. ET (TNT) on Sunday, July 6, from the Chicago Street Course.

How to watch the 2025 Grant Park 165

You can watch the Grant Park 165 on TNT or stream it via HBO Max.

Who won the Grant Park 165 last year?

Alex Bowman won the 2024 Grant Park 165 with raceday odds of 22-1. He opened as a 70-1 long shot.

💵 Best NASCAR betting sites

Want to bet on the Grant Park 165? Check out the best sports betting sites and best sportsbook promos for the race this weekend:

• FanDuel Promo Code
• DraftKings Promo Code
• Hard Rock Bet Promo Code

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