Chicago Cubs vs Pittsburgh Pirates Picks and Predictions

Chicago Cubs vs Pittsburgh Pirates Best Betting Picks

Chicago Cubs
Line: +144 Total: o7.5 Score: 0

Pittsburgh Pirates
Line: -175 Total: u7.5 Score: 0

Make your bets before 6:40pm EST 5/28/2026

Best Bets for the Chicago Cubs vs Pittsburgh Pirates

Below are the top 5 sports handicappers with picks on this game. Experts are listed in order based based on their hit rate from previous picks on the Chicago Cubs and/or Pittsburgh Pirates games and their overall MLB rankings. Visit their website directly to purchase their best bets for the day.

Rank	Sports Handicapper	30 Day MLB Record	MLB Season Record	Hit Rate	Website
#1	Jimmy Meyer	76-39 (66%), +$20,570	142-67 (68%), +$40,030	100%	View Website
#2	Richard Hartline	58-21 (73%), +$18,995	113-45 (72%), +$35,120	100%	View Website
#3	Swami Picks	46-39 (54%), +$2,160	85-87 (49%), -$5,065	100%	View Website
#4	Harold Windham	49-43 (53%), +$1,860	115-79 (59%), +$17,225	100%	View Website
#5	F&H Power Play	29-21 (58%), +$3,125	61-42 (59%), +$7,885	91%	View Website

Vegas Trends and Betting Odds

Chicago Cubs have won the past 1 out of 5 games while the Pittsburgh Pirates have won the past 3 out of 5 games. The Chicago Cubs are 1 and 4 on the most recent away games while the Pittsburgh Pirates are 2 and 3 at home. Vegas has the line at Pittsburgh Pirates -175 and the total at 7.5.

More hot bets: Chicago Cubs @ Pittsburgh Pirates, Los Angeles Angels @ Detroit Tigers, or Minnesota Twins @ Chicago White Sox.