Dan Kilbridge for Bookies.com

By Dan Kilbridge | | 9 mins

Ultimate Chicago Cubs Betting Guide, 2021 Odds & Tips

Ultimate Chicago Cubs Betting Guide, 2021 Odds & Tips
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The Chicago Cubs know the window is closing on a historic six-year run of success, including the franchise’s first World Series victory since 1908. But this team is still in competitive mode, for better or worse, hoping to get another year or two out of an aging core.

There’s still plenty of talent here and much has been made of the late-season struggles from the core of the lineup. We’ll soon find out if those cold bats late in the 2020 season were a matter of unfortunate timing or more serious signs of regression, and if the new-look starting rotation can keep the Cubs in contention in the NL Central.

Here are the MLB odds for the 2021 Chicago Cubs and four great prop bets to back.

Cubs World Series Odds (+4000 at Unibet)

Chicago is firmly in the middle of the pack in terms of World Series betting odds, currently even with the Cleveland Indians, Los Angeles Angels and Philadelphia Phillies at +4000 at Unibet .

The Cubs raced to a 13-3 start but faltered down the stretch in the shortened 2020 season, ultimately losing a two-game series to the Miami Marlins in the first round of the postseason. A talented lineup went cold for long stretches and the bullpen was a liability far too often.


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First baseman Anthony Rizzo, shortstop Javier Baez and third baseman Kris Bryant still have plenty to give. But they’re not spring chickens anymore and the long World Series odds reflect the many questions this team still needs to address before they can be considered a serious championship contender. However, unlike recent years, there’s actually value in 2021 – this team has been to the postseason five of the last six years and is now priced as a longshot at +4000.

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Cubs Odds To Win The NL (+2500 at FanDuel)

The Cubs are again in the middle of the pack in terms of odds to win the National League, listed ninth with +2500 odds at FanDuel .

The problem is that while the Cubs are still piecing things together, the NL is front-loaded with contenders ready to win right out of the gate. The Los Angeles Dodgers are a heavy World Series favorite and listed at +175 to win the pennant. The San Diego Padres (+400) were the story all offseason with splashy acquisitions and the Atlanta Braves (+550) look poised for another serious run.

The Cubs acquired outfielder Joc Pederson this offseason to add another lefty bat in the heart of the lineup. The big question is still pitching with a near-complete overhaul of the starting rotation, including the departures of Jon Lester and Yu Darvish. We’re not counting out the current Cubs roster, but it’s tough to see them taking out any of the top teams in the NL in October.

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Cubs Odds To Win The NL Central (+425 at FOX Bet)

The Cubs are defending champs in the NL Central and riding a streak of three division titles in five seasons. We wouldn’t be shocked to see them do it again in 2021 and there is value here with +425 MLB futures odds to take the Central at FOX Bet .

The St. Louis Cardinals are an even-money favorite at +100, with the Cincinnati Reds (+333) and Milwaukee Brewers (+375) also listed ahead of the Cubs. The Cardinals made the biggest move in the division by landing slugger Nolan Arenado from the Colorado Rockies. But they’re not perfect elsewhere and this should be a relatively close race from the top four in the division.

The Brewers didn’t do much to address their offensive issues last season. Same goes for the Reds, though Cincinnati does have a strong starting rotation. We think these teams are all pretty even at the top, creating value on the Cubs at +425.

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4 Great Cubs Prop Bets To Back

Cubs Over 78.5 Wins (-110, BetMGM)

The Cubs have had at least 84 wins in every full season since 2015. But they have big shoes to fill in the rotation and the bats under-performed almost across the board in the shortened 2020 season. Pederson is an upgrade over Kyle Schwarber at the plate. Bryant, Rizzo and Baez all struggled in the latter half of 2020, culminating in those three combining for a 1-for-24 showing in the postseason series with the Marlins.

We expect those hitters to bounce back; last season was a relatively small sample size under strange conditions.

The thing we like most about the over at BetMGM is that the Cubs get 19 games against the Pittsburgh Pirates, the worst team in baseball with longer MLB betting World Series odds (+25000) than anyone. Against a soft NL Central, 79 wins is certainly a reasonable ask.

Kyle Hendricks – NL Cy Young (+6600, DraftKings)

Hendricks was a bright spot again last year with a 2.88 ERA. The competition is tough against flamethrowers like Jacob deGrom, but the odds (+6600) at DraftKings are probably longer than they should be for a guy who finished third in Cy Young voting in 2016.


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He’s a durable option and now the unquestioned No. 1 starter for the Cubs. When Hendricks gets hot there’s no one better at locating, and his changeup is elite. He seemed to respond very well in 2020 under new manager and former teammate David Ross, who gave him a much longer leash than Joe Maddon did in the middle innings. We think Hendricks is worth a flyer as a longshot bet.

Javier Baez – NL RBI Leader (+4000, PointsBet)

Baez led the NL with 111 RBI in 2018 but has admittedly struggled with his focus in recent years. He has dedicated himself to becoming an All Star-caliber shortstop again in 2021 and should be sitting pretty in the lineup.

Ross liked to use Baez in the No. 5 spot last season and Baez could drive in a lot of runs with Pederson, Bryant and Rizzo ahead of him. Of all the Cubs stars who struggled in 2020, we think Baez is most likely to bounce back in a big way, making him worth a flier at PointsBet .

David Ross – NL Manager of the Year (+1500, DraftKings)

It was obviously an unusual first season for Ross in Chicago. The Cubs needed a change and Ross seemed to strike a nice balance in managing several former teammates. Now that he has had time to settle in and get ready for a 162-game season, we expect him to further assert himself in the dugout.

This can also be a narrative-driven award and you can just imagine how the media would eat it up if Ross – who homered in his final career at-bat during Game 7 of the 2016 World Series win over the Indians – helps the Cubs exceed all expectations with another 90-win season in the Windy City. Get these odds at DraftKings .

About the Author

Dan Kilbridge for Bookies.com
Dan Kilbridge
Handicapper Dan Kilbridge writes about college football, MLB and other sports for Bookies.com after spending three years covering Tiger Woods’ comeback and the PGA for Golfweek.