Kenny G leaned to Baltimore at +155, arguing Chicago is overpriced while slumping. Brandon Young (0-5, 6.63 ERA) is volatile but comes off a strong outing versus Toronto, whereas Cubs starter Colin Rea (8-5, 4.25) has been tagged in back-to-back starts against Milwaukee and Kansas City. Chicago’s explosive offense has gone quiet, scoring 3, 1, 10, 3, 4 and 5 over its last six, and the bullpen just coughed up Saturday’s game. Baltimore travels poorly (23-32) yet owns an MLB-best 35-19-1 road under record, so a low-scoring script would favor the dog. With the Cubs stuck two games behind Milwaukee and pressing, Kenny thinks the value sits squarely on the Orioles.

Brad Free Pick Dawgz recommended laying a half-run with the Chicago Cubs in the first five innings against Baltimore. He labeled the bet "strictly a fade of Brandon Young," predicting Chicago’s top-10 first-five OPS will punish Young’s shaky command early and have the Cubs in front by the end of the fifth.

After Saturday’s gut-punch 4-3 loss in which Chicago blew a 3-0 eighth-inning lead, Mark is going right back to the well with the Cubs at -170 as the first leg of his money-line parlay. He expects Javier Assad’s replacement Shota Imanaga (listed as Rhea in some books) to stabilize the rotation and believes the Cubs, still 10-5 in their last 15, will close out the series against an Orioles bullpen that has been worked hard all weekend.

Drew Martin recommended backing the Chicago Cubs on the moneyline (or a −1 run alternative) with Colin Rea on the hill. Rea sits at 8-5 and still carried his usual velocity even while getting tagged in two tough recent spots—wind howling out at Wrigley versus Kansas City and a red-hot Milwaukee lineup. Baltimore is expected to recall a starter from AA Chesapeake who sports a 6.50 ERA, has surrendered 19 hits over his last three MLB outings, averages fewer than five innings per start, and owns an 0-5 record. Martin also pointed out Chicago’s bullpen rates better than Baltimore’s, strengthening the late-game edge.

Just A Bet Outside highlighted the Cubs relief corps as a sneaky buy-low angle for totals and late-inning sides. Chicago’s bullpen posted an ugly 6.00 ERA during July, but its 3.71 Sierra is actually better than several ‘top-seven’ staffs on his board, indicating massive negative luck. No major trades weakened the group, so Steven expects run prevention to rebound quickly. Bettors can look to play Cubs unders, live-bet Chicago when tied after the sixth, or grab plus-money on full-game lines before the market catches up to the bullpen’s expected improvement.

The Bettor Mark recommended laying the –142 on the Cubs in their first game back at Wrigley. He expects an emotional bump from Friday’s Ryne Sandberg celebration and noted Chicago’s brutal road split flips when they return home. Facing rookie Cade Horton versus Trevor Rogers, he thinks the inspired lineup prevails and even floated side markets such as a walk-off or first-inning homer because "weird stuff can happen" on nights like this, but the core play is Cubs moneyline.

Kenny G said the plus-125 price on Baltimore is enticing enough to warrant a play despite calling the overall matchup "pretty much a stay-away". His optimism is rooted in Trevor Rogers’ 1.49 ERA through eight starts, highlighted by a seven-inning, one-hit gem in an 18-0 rout of Colorado. The Orioles have suddenly surged at the plate, scoring 8-plus runs in four of their last six, and recently took three of four from Toronto. Kenny acknowledged the Baltimore bullpen is a weakness but believes Chicago could be flat after an emotional 10-3 get-away win against Milwaukee. Rookie Cade Horton has tossed back-to-back scoreless starts but is still only at a 3.67 ERA, and the Cubs relief corps has crept up to 3.86. With Chicago priced as a -150 favorite and the Orioles owning MLB’s best road under record (35-19-1), Kenny thinks the recent hitting spike and Rogers’ form make Baltimore the sharper side at plus money.

Guy Boston Sports said Jackson Holliday is a strong addition to the five-leg parlay by taking the over 0.5 hits. Over the last 30 days Holliday owns a .333 batting average and .926 OPS versus right-handed pitching such as Cade Horton, well above his .272 season mark. The tout stressed that Holliday’s splits have been better against righties all season and nothing in Horton’s profile suggests he will cool him off, making one base knock the most likely outcome.

Guy Boston Sports advised taking Jackson Holliday to record a hit at Wrigley Field, noting a 70 % cash rate over his last 10 games (1.2 hits per) and a 67 % rate for the full 2025 season. Outlier shows Holliday has hit in 5 of his last 6 road contests (83 %). The matchup lines up: right-hander Cade Horton’s batting-average-allowed jumps from .264 to .290 versus left-handed hitters, while Holliday’s slash line versus righties over the past 30 days is .333 AVG/.926 OPS. Statcast pitch data further tilts the edge—Holliday owns elevated wOBA numbers against four of Horton’s five most-used pitches, including a .356 mark against his 49 % fastball usage and .372 versus the slider. FanDuel posts the alternate over 0.5-hit prop at –220, which the tout slotted as leg two of his Freaky Friday parlay.

Bill Harrelson advised betting Austin Hays under 1.5 total bases, labeling the Underdog line a clear error given the market. Hays has stayed below this threshold in nine of his past ten games—including five straight—and 14 of his last 20 (70 %). Over a 59-game 2025 sample he is under in 58 % of contests (34/59), while last season he failed to reach two bases in 56 of 80 games (70 %). DraftKings, Caesars, Hard Rock, Novig, and Fliff are all heavily juiced to the under, underscoring Harrelson’s claim that "everyone and their mother thinks Underdog messed this one up." He also noted Hays has fallen short in five consecutive home games, one more reason to attack the line. With no major changes in role or batting-order spot and the consensus pricing heavily tilted toward the under, Harrelson expects another quiet night at the dish from Hays.