The Chicago White Sox have run into a lot of trouble against good teams, posting an underwhelming 18-27 record against those over .500, which describes their crosstown rivals, the Chicago Cubs.
My White Sox vs. Cubs predictions and MLB picks expect those struggles to continue against one of the league's best offenses on Monday, Aug. 17.
Who will win White Sox vs Cubs today: Chicago Cubs (-170)
Luis Castillo has not had a good season, and things have looked especially bleak when the competition level goes up.
The veteran righty has posted a 6.75 ERA and allowed 2.57 HR/9 over six starts against Top-10 opponents in OBP vs. right-handed pitching.
The Chicago Cubs sit fifth on the season and sixth over the last 30 games. They will be tough for Castillo to slow down.
Shota Imanaga ranks fourth in SIERA among today’s starters and has a better chance of slowing the Chicago White Sox offense down.
Back the Cubs -190.
COVERS INTEL: Castillo ranks in the 13th percentile in Pitcher Run Value and will be ripe for the picking against the league's second-highest-scoring offense.
White Sox vs Cubs Over/Under pick: Over 8.5 (+109)
Power is the easiest path to bulk production, and we should see plenty of it in this game.
Castillo has posted a much higher ERA on the road while allowing 1.98 HR/9. That’s noteworthy, as he has only made one home start away from the friendly confines of T-Mobile Park.
The Cubs are seventh in total homers vs. righties, and conditions make for an 11% HR boost at Wrigley today.
Imanaga has allowed 1.83 HR/9 this season and will have to contend with a White Sox offense slotting fourth in ISO vs. lefties.
Play to -115.
White Sox vs Cubs home run prediction: Pete Crow-Armstrong (+275)
Pete Crow-Armstrong is once again the priority target for power.
Castillo has given up a ton of power to left-handed bats, allowing a .232 ISO and close to two homers per nine innings.
The splits work in PCA’s favor, as does the pitch mix. Castillo predominantly uses the fastball, slider, and changeup vs. lefties.
PCA has a .274 ISO against those three pitches against RHP. Add in the favorable park factors, and this is another good spot to back the NL MVP contender.
Take it to +260.
- ML/RL bets: 81-73, -8.55 units
- Over/Under bets: 82-66-6, +6.09 units
White Sox vs Cubs weather
The forecast calls for temperatures in the 70s with winds blowing west. Slight boost to the bats.
White Sox vs Cubs odds
- Moneyline: White Sox +145 | Cubs -170
- Run line: White Sox +1.5 (-145) | Cubs -1.5 (+125)
- Over/Under: Over 8.0 (-115) | Under 8.0 (-105)
White Sox vs Cubs trend
The Cubs have won 33 of their last 50 games (+11.65 units, 18% ROI). Find more MLB betting trends for White Sox vs. Cubs.
How to watch White Sox vs Cubs and game info
| Location | Wrigley Field, Chicago, IL |
| Date | Monday, August 17, 2026 |
| First pitch | 8:05 p.m. ET |
| TV | CHSN, MARQ |
| White Sox starting pitcher | Luis Castillo (4-9, 4.96 ERA) |
| Cubs starting pitcher | Shota Imanaga (8-9, 3.74 ERA) |
White Sox vs Cubs latest injuries
Odds are correct at the time of publishing and are subject to change.
Not intended for use in MA.
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