Pirates vs. Cubs Dunkel MLB Picks, Predictions and Prop Bets - May 27

The Pittsburgh Pirates bring a three-game win streak into a home contest versus the Chicago Cubs at 6:40 p.m. ET on Wednesday. Bubba Chandler (1-6, 4.79 ERA) gets the start for the Pirates, who are 29-26 this season and fourth in the NL Central. Jameson Taillon (2-4, 5.20 ERA) is the expected starter for the Cubs, who are 29-26 and fifth in the NL Central.

The moneyline odds for the Pirates (-114) versus the Cubs (-105) are tight. The contest has a total set at 8.5.

Pirates vs. Cubs Odds, Game Time

• Game day: Wednesday, May 27, 2026
• Game time: 6:40 p.m. ET
• Location: Pittsburgh, Pennsylvania
• Stadium: PNC Park
• Favorite: Pirates (-114)
• Underdog: Cubs (-105)
• Over/under: 8.5

How to Watch Pirates vs. Cubs

• TV Channel: SportsNet PT and MARQ
• Live Stream: Fubo (Watch for free)

Bet now on FanDuel Sportsbook!

Pirates vs. Cubs: Betting the Moneyline

• The Pirates have won 62.5% of the games this season when they were the moneyline favorite (20-12).
• Chicago has been underdogs in 17 games this season and has come away with the win eight times (47.1%) in those contests.
• Pittsburgh has a record of 19-12 in games when sportsbooks favor them by at least -114 on the moneyline.
• This season, the Cubs have been victorious seven times in 16 chances when named as an underdog of at least -105 or worse on the moneyline.
• The Pirates have a 53.3% chance to win this contest based on the moneyline's implied probability.
• The Cubs have an implied victory probability of 51.2% according to the moneyline set for this matchup.

Pirates vs. Cubs: Betting the Spread & Total

• The Pirates have played in 55 games with an over/under set, and have combined with their opponents to go over the total 28 times (28-25-2).
• Chicago and its opponents have hit the over in 30 of its 55 games with a total this season.
• The Pirates have collected a 29-26-0 record ATS this season (covering 52.7% of the time).
• The Cubs are 21-34-0 against the spread in their 55 games that had a posted line this season.