Cubs vs. White Sox Betting Odds: Windy City Showdown Alive And Well

The Crosstown Cup will stay in the Southside regardless of what happens this weekend when the Chicago Cubs and Chicago White Sox meet for a pair of games at Guaranteed Rate Field on Saturday and Sunday, May 28-29.

Earlier this month the White Sox (22-22) swept both games played against the Cubs (18-26) at Wrigley Field. That means the worst the Sox can do is split, which means Tony La Russa’s club will retain the coveted Cup that goes to the winner of the City Series.

Last year the Sox won five of the six games between the two storied franchises. In 2020 and 2019, the teams split. All time, the White Sox lead the City Series, 72-64. The two Windy City teams first played in the regular season in 1997.

There are plenty of sports betting bonuses available for the weekend’s games, including up to $1,050 free with this DraftKings Promo Code, and a $250 deposit match bonus with BetRivers Bonus Code SHARP250.

Cubs vs. White Sox Betting Odds

SportsbookSunday MoneylineSunday Run LineSunday Total
DraftKingsWhite Sox -150
Cubs +130
White Sox -1.5 (+135)
Cubs +1.5 (-155)
Over 7.5 (+105)
Under 7.5 (-125)
BetMGMWhite Sox -160
Cubs +135
White Sox -1.5 (+125)
Cubs +1.5 (-155)
Over 7 (-120)
Under 7 (+100)
PointsBetWhite Sox -155
Cubs +130
White Sox -1.5 (+145)
Cubs +1.5 (-176)
Over 7 (-115)
Under 7 (-105)

Cubs Pitching

It should be the Miley & Smyly Show for the Cubbies this weekend, as left-handers, Wade Miley and Drew Smyly are next in line to take the hill for manager David Ross. It’s unusual for a team to place lefties back-to-back in a rotation (and the Cubs have been running a third southpaw to the mound Justin Steele which makes three wrong-handers in a row), but maybe the Cubs know something we don’t.

White Sox Pitching

The Sox have grappled with injuries this season, but the rotation has settled into a five-man groove, with Johnny Cueto, the Man With a Million Deliveries, serving as a sixth arm when needed. The Pale Hose will indeed send Cueto to the mound on Saturday, and Dylan Cease will toe the rubber on Sunday.

The White Sox rank fourth in the AL in Fielding Independent Pitching, but can shoot themselves in their white socks by walking batters: the rotation ranks first in the league in free passes.

AP Photo/Ross D. Franklin

About the Author

Dan Holmes

Dan Holmes has written three books about sports. He previously worked for the National Baseball Hall of Fame and Major League Baseball. He enjoys writing, running, and lemon bars. He lives near Lake Michigan with his daughters and usually has an orange cream soda nearby.