Cubs vs White Sox Picks and Predictions: Sox and the City

It's a Windy City rubber match as the Sox host their cross-town rivals for a series-deciding game. And while Kyle Hendricks has been solid this season, he could come under fire here. Find out why with our Cubs vs White Sox picks.

Last Updated: Aug 29, 2021 9:56 AM ET Read Time: 4 min
Dylan Cease MLB Chicago White Sox
Photo By - USA TODAY Sports

The conclusion of a three-game Crosstown Classic between the Chicago Cubs and Chicago White Sox will unfold at Guaranteed Rate Field in Chicago, Illinois on Sunday, August 29. The Cubs came away with a stunning victory Saturday, so the winner of this game will take this series. 

Will the Cubs surprise the White Sox one more time? Find out in our Cubs vs. White Sox picks and predictions. 

Cubs vs White Sox game info

Location: Guaranteed Rate Field
Date: Sunday, August 29, 2021
Time: 2:10 p.m. ET
TV: NBCSCH, Marquee Sports Network

Cubs vs White Sox odds

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Starting pitchers

Kyle Hendricks (14-5, 4.09 ERA): It’s a shame for Hendricks that he was left behind at the deadline, as the righty is still good enough to be a big part of a winning team’s rotation. The 31-year-old continues to baffle opposing hitters with his ridiculous command, and he recently pitched six innings of two-run ball against this White Sox team on August 6.

Hendricks did, however, give up seven hits in that game, so there was some trouble there. He has also given up 14 runs over his last three starts.  

Dylan Cease (10-6, 3.92 ERA): Cease struck out 10 batters and gave up three runs in five innings against the Cubs on August 8, and the righty is going to be more confident when he faces them this time around.

Cease is coming off a start in which he gave up one run in seven innings against the Toronto Blue Jays, and he genuinely seems to be heating up down the stretch. The White Sox have won in four of his last six trips to the hill. 


Be sure to monitor the gametime conditions with our MLB weather info.

Key injuries

Cubs: C Willson Contreras (out)
White Sox: OF Billy Hamilton (out)
Find our latest MLB injury reports.

Betting trend to know

The White Sox are 5-1 in their last five interleague games. Find more MLB betting trends for Cubs vs. White Sox.

Runline pick

The Cubs came out and punched first in Saturday’s game and the White Sox never responded. David Ross’ team really got to Lance Lynn in that one, and now the Sox are going to need to really lock in and take this one seriously. Fortunately for them, some of the team’s best hitters have absolutely crushed Hendricks in the past, and that includes superstar Jose Abreu. In his career, Abreu is 11 for 19 with a double, a homer and 13 RBIs against Hendricks. He has also drawn two walks, showing that he really makes the Cubs veteran nervous. Tim Anderson is another player that has had some success against Hendricks, as he is 6 for 16 against him. 

Not only do the White Sox have a chance of knocking Hendricks around a little, but Cease has been stellar as of late. The 25-year-old misses a ton of bats, which is bad news for a Cubs team that is first in the league in strikeout rate this season. Cease also has a 2.61 ERA when pitching at home this season, which is a heck of a lot better than his 5.37 ERA on the road. 

PREDICTION: White Sox -1.5 (-115)

Over/Under pick

With the White Sox having some hitters that won’t fear Hendricks in this game, it wouldn’t be too surprising if the Sox scored three or so on the righty. The White Sox would then have the pleasure of working against a below-average bullpen for a couple of innings, which is why the team is such a good bet to win this game — and win it by more than one run.

With that said, this total still seems a little too high in a matchup between two starters of this caliber. Hendricks should be able to limit any major damage against the Sox, and Cease is on a tear coming into this game. 

PREDICTION: Under 8.5 (-110)

Cubs vs White Sox betting card

  • White Sox -1.5 (-115) 
  • Under 8.5 (-110)

Picks made on 8/29/2021 at 1:45 a.m. ET

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