Best Month for Cubs? How Team Fared Recently

Best Month for Cubs? How Team Fared Recently
Fact Checked by Pat McLoone

The Chicago Cubs haven’t made the playoffs in a full season since 2018. While that’s a mild drought, historically speaking, for the franchise located at Waveland and Sheffield, it comes after the Cubbies made it in four consecutive seasons.

Since that run, which included their first World Series championship in 108 years, expectations aren’t what they used to be, certainly not in Illinois sports betting. But considering the Cubs play in the National League Central, they should be playoff contenders.

After two sub-.500 seasons, the Cubs finished 2023 with an 83-79 record. They just missed a wild card berth, falling a game behind the Miami Marlins and Arizona Diamondbacks. ESPN BET Illinois has the Cubs and the St. Louis Cardinals as co-favorites to win the NL Central this season, with odds of +175.

The start of the 2024 campaign is nearly three weeks away. With that in mind, wanted to know which month was the best for the Cubs over the past three seasons.

Chicago Cubs Best Month

Rank, Month Record Winning Pct.
1. May 41-42 .494
2. August 40-44 .476
3. September 38-42 .475
4. July 35-41 .461
5. June 36-44 .450
6. April 32-41 .438

This breakdown from likely won’t be on Illinois betting apps.

What Month Might Decide Chicago Postseason Fate?

While the three-year data shows May as the best month, it actually was the worst for last year’s team. They won just 10 of 28 games in the month. The dog days of August last season is when the Cubs made their second-half surge toward the playoffs, going 18-9 for the month, but they slipped to 12-16 in September.

May could be a good month for the Cubs this season. While they do have six games scheduled against the Atlanta Braves, the team that posted the best record in baseball last season, they also have seven games against a Milwaukee Brewers club that’s expected to rebuild after winning the NL Central last season, and the Pittsburgh Pirates, a team expected to finish toward the bottom of the division.

September again could be a crucial month for the Cubs’ playoff chances as the month includes two three-game series vs. the New York Yankees and at the Los Angeles Dodgers early in the month. The final week includes a pair of three-game series at the Philadelphia Phillies and home vs. the Cincinnati Reds, two teams many baseball pundits expect will contend for playoff spots this season.

As both the Diamondbacks and the defending champion Texas Rangers proved last year, having the best regular season record doesn’t always lead to having the best postseason run. It’s just about getting to October.

Think the Cubs might just win it all this season? The oddsmakers at BetMGM Illinois are offering +3000 on Chicago in its World Series futures market.

Make sure to visit regularly for the latest news on Chicago teams and the best Illinois sports betting promo codes around.

Bonus Bets Expire in 7 Days. One New Customer Offer Only. Must be 21+ to participate & present in IL. In partnership with Par-A-Dice Hotel Casino. Gambling problem? Call 1-800-GAMBLER or text ILGAMB to 53342. Visit for Terms & Conditions. US promotional offers not available in NY, NV, or Puerto Rico.


Steve is an accomplished, award-winning reporter with more than 20 years of experience covering gaming, sports, politics and business. He has written for the Associated Press, Reuters, The Louisville Courier Journal, The Center Square and numerous other publications. Based in Louisville, Ky., Steve has covered the expansion of sports betting in the U.S. and other gaming matters.

Cited by leading media organizations, such as: