White Sox vs. Cubs
Prediction, Odds & Props
May 17 | MLB AI Picks

Updated: 2025-05-15T03:31:50.923562ZBy Remi at Leans.AI — AI picks for ATS, ML, OU & props

The Chicago Cubs and Chicago White Sox continue their Crosstown Classic on Saturday, May 17, 2025, at Wrigley Field, with first pitch scheduled for 1:20 p.m. CT. The Cubs, leading the NL Central, aim to extend their dominance over the struggling White Sox in this storied rivalry.

Get key insights, betting trends, and AI-powered predictions to help incorporate into your betting strategies.

AI Sports Betting Algorithm Remi

GAME INFO

Date: May 17, 2025

Start Time: 2:20 PM EST​

Venue: Wrigley Field​

Cubs Record: (26-19)

White Sox Record: (14-31)

OPENING ODDS

CHW Moneyline: +227

CHC Moneyline: -281

CHW Spread: +1.5

CHC Spread: -1.5

Over/Under: 10.5

CHW
Betting Trends

  • The White Sox have a 23-19 record against the spread (ATS) this season, indicating they often outperform expectations despite their overall struggles.

CHC
Betting Trends

  • The Cubs hold a 25-19 ATS record, reflecting consistent performance and reliability for bettors throughout the season.

MATCHUP TRENDS

  • Despite their poor overall record, the White Sox have been competitive in betting markets, covering the spread in 23 of 42 games. Conversely, the Cubs have been strong at home, with an 11-9 ATS record at Wrigley Field, showcasing their home-field advantage.

CHW vs. CHC
Best Prop Bet

  • Remi's searched hard and found the best prop for this matchup: S. Burke over 9.5 Fantasy Score.

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Chicago White Sox vs Chicago Cubs Prediction & Odds:
Free MLB Betting Insights for 5/17/25

The second installment of the 2025 Crosstown Classic between the Chicago White Sox and Chicago Cubs on May 17 at Wrigley Field offers a compelling contrast between a rebuilding club and a postseason hopeful. The Cubs enter the game with a 25-19 record and sit atop the NL Central, propelled by an explosive offense and reliable starting pitching. Their lineup, which ranks fourth in Major League Baseball in OPS, is powered by the likes of Seiya Suzuki, Kyle Tucker, and breakout star Pete Crow-Armstrong, who has not only driven in 30 runs but also provided elite outfield defense and speed on the basepaths. Matthew Boyd will take the mound for the Cubs, bringing a 3-2 record and a 2.78 ERA into the contest, having established himself as a dependable left-handed arm who can suppress both lefties and righties with a combination of deception and command. On the flip side, the White Sox are in the midst of a challenging season, holding a 14-30 record and grappling with the growing pains of a roster in transition. Under first-year manager Will Venable, Chicago has shifted focus toward development, giving young players like catcher Edgar Quero and slugger Tim Elko significant opportunities. Quero has shown signs of becoming a long-term foundational piece, while Elko recently provided a spark with a clutch three-run homer. On the mound for the South Siders will be right-hander Sean Burke, who is 2-4 with a 4.15 ERA, still searching for consistency but showing glimpses of promise in a starting role.

Despite their overall struggles, the White Sox have been surprisingly competitive in betting markets, compiling a 23-19 ATS record, suggesting they keep games tighter than their win-loss column suggests. Meanwhile, the Cubs have also been a reliable team for bettors with a 25-19 ATS record, and their 11-9 home mark at Wrigley shows they often handle business in front of the home crowd. The Cubs are riding a five-game win streak in this rivalry and are heavily favored to continue that trend, especially given their balanced offensive approach, improved bullpen, and the leadership of manager Craig Counsell. However, rivalry games tend to defy expectations, and with the White Sox playing with nothing to lose and a roster of young talent eager to prove themselves on a big stage, the outcome may be more competitive than records alone suggest. The key to the game will likely hinge on whether the Cubs can jump on Burke early and give Boyd run support, allowing them to lean on their bullpen with a lead, while the White Sox will hope to scrap out timely hits and find stability on the mound long enough to give their offense a chance to respond. With a packed house at Wrigley, city pride on the line, and playoff positioning at stake for the Cubs, expect a spirited contest that will test both teams’ execution and poise under the bright lights of Chicago’s fiercest baseball rivalry.

Chicago White Sox White Sox MLB Preview

The Chicago White Sox enter Saturday’s Crosstown Classic game at Wrigley Field as clear underdogs, burdened by a 14-30 record that places them near the bottom of the American League standings, but determined to use this rivalry as a measuring stick for their young, evolving roster. With a new managerial regime under Will Venable, the White Sox are leaning into a rebuild that emphasizes player development, defensive fundamentals, and the long-term evaluation of young talent rather than immediate results. The lineup has seen flashes of promise from catcher Edgar Quero, who has quickly earned the trust of the pitching staff and shown solid plate discipline, and slugging corner infielder Tim Elko, whose recent three-run homer against these same Cubs was a rare jolt of power for a lineup that ranks near the bottom of the league in run production and slugging percentage. These young hitters are getting extended looks in an offense that has struggled with consistency, particularly with runners in scoring position, and lacks the veteran anchors it once leaned on. On the mound, the White Sox will turn to right-hander Sean Burke, who carries a 2-4 record and 4.15 ERA into this matchup, representing one of the few bright spots in a rotation that has battled injuries, inconsistency, and limited depth. Burke has shown the ability to miss bats with his fastball-slider mix, but command lapses have hurt him at times, and his efficiency will be critical against a patient Cubs lineup that excels at working counts and driving up pitch totals.

While the team’s road record sits at a woeful 5-18, the White Sox have been surprisingly competitive in the eyes of bettors, posting a 23-19 ATS record that suggests they often keep games closer than the final outcome might indicate. Defensive lapses, bullpen volatility, and lack of experience have all played roles in their inability to close out games, but the team remains feisty, especially in rivalry matchups where young players have a chance to make a name for themselves. The club is in search of a spark, and Wrigley Field under the afternoon sun could be the ideal stage for players like Bryan Ramos, Colson Montgomery, or Elko to deliver statement performances against a Cubs team expected to win. While expectations are understandably low given the current state of the roster and the depth of talent across the diamond, the White Sox enter this game with the mentality of spoilers—eager to disrupt their rivals’ momentum, gain experience under pressure, and steal a victory in enemy territory. Saturday’s game is less about standings for this group and more about identity-building, grit, and finding incremental progress as they forge a new path forward in one of the league’s most visible rebuilds. For the White Sox, anything less than maximum effort against their crosstown foes would betray the mission Venable has instilled—one built on pride, opportunity, and the future.

The Chicago Cubs and Chicago White Sox continue their Crosstown Classic on Saturday, May 17, 2025, at Wrigley Field, with first pitch scheduled for 1:20 p.m. CT. The Cubs, leading the NL Central, aim to extend their dominance over the struggling White Sox in this storied rivalry. Chicago White Sox vs Chicago Cubs AI Prediction: Free MLB Betting Insights for May 17. Credit USA TODAY/IMAGN

Credit: USA TODAY/IMAGN

Chicago Cubs Cubs MLB Preview

The Chicago Cubs enter Saturday’s home tilt against the White Sox riding a wave of early-season momentum that has them leading the NL Central with a 25-19 record and looking every bit the part of a playoff contender. Under manager Craig Counsell, the Cubs have crafted a well-balanced identity built on strong starting pitching, timely hitting, and a quietly improving bullpen that has helped them consistently close out games. Their offense, ranked fourth in MLB in OPS, has been a force at Wrigley Field, where they hold an 11-9 record and have outscored opponents by a comfortable margin over the past few weeks. Seiya Suzuki has been a steady presence in the middle of the lineup, consistently hitting for average and power while drawing walks and playing excellent defense in right field. Kyle Tucker, acquired to boost the team’s power numbers, has delivered on that promise with a combination of slugging and baserunning, while Pete Crow-Armstrong has emerged as one of the most exciting young players in the National League, driving in 30 runs and playing Gold Glove-level defense in center field. On the mound, left-hander Matthew Boyd will get the start, bringing a 3-2 record and impressive 2.78 ERA into the contest. Boyd has embraced a savvy veteran’s approach this season, mixing pitches effectively and keeping hitters off balance with a well-tunneled changeup and sweeping slider. He’ll look to attack a White Sox lineup that has struggled to find any sort of rhythm or consistency at the plate, especially against left-handed pitching.

The Cubs’ defense has also been a bright spot, helping the pitching staff maintain one of the better team ERAs in the National League. In high-leverage situations, the bullpen has tightened up, with reliable arms like Adbert Alzolay and Mark Leiter Jr. showing the ability to lock down eighth and ninth innings. One of the most promising indicators of Chicago’s season has been their ability to win close games and maintain focus during rivalry matchups, where emotional swings can often dictate tempo. Against the White Sox, a team they’ve beaten five straight times, the Cubs know the importance of taking care of business at home and asserting their superiority early to avoid giving confidence to a rebuilding opponent. Saturday’s game will also serve as another test of how the Cubs manage expectations—no longer flying under the radar, they now have a target on their backs in a division that remains tightly contested. Counsell’s leadership has been crucial in keeping the team grounded and sharp, and with a healthy core and consistent production throughout the order, the Cubs appear poised to continue their upward trajectory. A win over the White Sox wouldn’t just solidify bragging rights in the city—it would further cement Chicago’s north-side squad as one of the National League’s most complete and consistent teams as the calendar moves toward summer. With playoff aspirations clearly in view, expect the Cubs to play with urgency, confidence, and a sense of pride in front of what will undoubtedly be a packed and lively Wrigley crowd.

Chicago White Sox vs. Chicago Cubs Prop Picks (AI)

AI algorithm Remi is pouring through tons of datapoints on each line. In fact, anytime the White Sox and Cubs play there’s always several intriguing angles to key in on. Not to mention games played at Wrigley Field in May almost always follow normal, predictable patterns.
Remi's searched hard and found the best prop for this matchup: S. Burke over 9.5 Fantasy Score.

Chicago White Sox vs. Chicago Cubs Prediction (AI)

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Remi, our AI sports algorithm, has been pouring over mountains of data from every past game between the White Sox and Cubs and using recursive machine learning and kick-ass AI to analyze the data to a single cover probability.

Oddly enough, we’ve seen the AI has been most fixated on the linear correlation of factor knucklehead sportsbettors often put on Chicago Cubs’s strength factors between a White Sox team going up against a possibly deflated Cubs team. It appears the true game analytics might reflect a moderate lean against one Vegas line in particular.

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Below is our current AI Chicago White Sox vs Chicago Cubs picks, computer picks White Sox vs Cubs, best bets, model edges, confidence ratings.

DATE GAME LEAN %WIN UNITS LEVEL
MLB 9/26 DET@BOS UNLOCK THIS PICK 5 EXECUTIVE Locked EXECUTIVE
MLB 9/26 BAL@NYY UNLOCK THIS PICK 4 INTEL Locked INTEL
MLB 9/26 ARI@SD UNLOCK THIS PICK 4 EXECUTIVE Locked EXECUTIVE
MLB 9/26 NYM@MIA UNLOCK THIS PICK 1 INTEL Locked INTEL
MLB 9/26 NYM@MIA GET FREE PICK NOW 1
MLB 9/26 COL@SF UNLOCK THIS PICK 0 INTEL Locked INTEL

These picks update as information changes—injury reports, weather, and market movement. Each line shows our model’s fair price, the edge versus the market, and a unit confidence rating (1–10). Odds and availability vary by sportsbook and time. Edges are computed against the listed price; value may change after line moves. Always shop for the best number. See the full MLB schedule.

White Sox Betting Trends

The White Sox have a 23-19 record against the spread (ATS) this season, indicating they often outperform expectations despite their overall struggles.

Cubs Betting Trends

The Cubs hold a 25-19 ATS record, reflecting consistent performance and reliability for bettors throughout the season.

White Sox vs. Cubs Matchup Trends

Despite their poor overall record, the White Sox have been competitive in betting markets, covering the spread in 23 of 42 games. Conversely, the Cubs have been strong at home, with an 11-9 ATS record at Wrigley Field, showcasing their home-field advantage.

Chicago White Sox vs. Chicago Cubs Game Info

Chicago White Sox vs Chicago Cubs starts on May 17, 2025 at 2:20 PM EST.

Spread: Chicago Cubs -1.5
Moneyline: Chicago White Sox +227, Chicago Cubs -281
Over/Under: 10.5

Chicago White Sox: (14-31)  |  Chicago Cubs: (26-19)

Remi's searched hard and found the best prop for this matchup: S. Burke over 9.5 Fantasy Score.. Prices move—always shop for the best number.

Despite their poor overall record, the White Sox have been competitive in betting markets, covering the spread in 23 of 42 games. Conversely, the Cubs have been strong at home, with an 11-9 ATS record at Wrigley Field, showcasing their home-field advantage.

CHW trend: The White Sox have a 23-19 record against the spread (ATS) this season, indicating they often outperform expectations despite their overall struggles.

CHC trend: The Cubs hold a 25-19 ATS record, reflecting consistent performance and reliability for bettors throughout the season.

See our latest MLB picks and odds pages for 2025 to compare prices before you bet.

Chicago White Sox vs. Chicago Cubs Odds

Remi is pouring through loads of data points on each team. In fact, anytime the Chicago White Sox vs Chicago Cubs trends are analyzed, there’s always several intriguing observations to key in on. Not to mention games played at extreme travel distance can often follow normal, predictable patterns.

Chicago White Sox vs Chicago Cubs Opening Odds

CHW Moneyline: +227
CHC Moneyline: -281
CHW Spread: +1.5
CHC Spread: -1.5
Over/Under: 10.5

Chicago White Sox vs Chicago Cubs Live Odds

Games PTS ML SPR O/U
Sep 27, 2025 1:06PM EDT
Baltimore Orioles
New York Yankees
9/27/25 1:06PM
Orioles
Yankees
+192
-235
+1.5 (-110)
-1.5 (-110)
O 9 (+100)
U 9 (-120)
Sep 27, 2025 2:21PM EDT
St Louis Cardinals
Chicago Cubs
9/27/25 2:21PM
Cardinals
Cubs
 
-178
 
-1.5 (+115)
O 9.5 (+100)
U 9.5 (-120)
Sep 27, 2025 3:09PM EDT
Tampa Bay Rays
Toronto Blue Jays
9/27/25 3:09PM
Rays
Blue Jays
+135
-160
+1.5 (-160)
-1.5 (+135)
O 8.5 (-110)
U 8.5 (-110)
Sep 27, 2025 4:06PM EDT
Chicago White Sox
Washington Nationals
9/27/25 4:06PM
White Sox
Nationals
+100
-120
+1.5 (-205)
-1.5 (+170)
O 8.5 (-110)
U 8.5 (-110)
Sep 27, 2025 4:06PM EDT
Colorado Rockies
San Francisco Giants
9/27/25 4:06PM
Rockies
Giants
+192
-235
+1.5 (-110)
-1.5 (-110)
O 8 (-105)
U 8 (-115)
Sep 27, 2025 4:11PM EDT
New York Mets
Miami Marlins
9/27/25 4:11PM
Mets
Marlins
-130
+110
-1.5 (+130)
+1.5 (-155)
O 8 (-120)
U 8 (+100)
Sep 27, 2025 4:11PM EDT
Detroit Tigers
Boston Red Sox
9/27/25 4:11PM
Tigers
Red Sox
+110
-130
+1.5 (-190)
-1.5 (+158)
O 9 (+100)
U 9 (-120)
Sep 27, 2025 6:05PM EDT
Minnesota Twins
Philadelphia Phillies
9/27/25 6:05PM
Twins
Phillies
+175
-210
+1.5 (-120)
-1.5 (+100)
O 8.5 (-115)
U 8.5 (-105)
Sep 27, 2025 7:11PM EDT
Cincinnati Reds
Milwaukee Brewers
9/27/25 7:11PM
Reds
Brewers
+115
-135
+1.5 (-190)
-1.5 (+158)
O 7.5 (-120)
U 7.5 (+100)
Sep 27, 2025 7:15PM EDT
Pittsburgh Pirates
Atlanta Braves
9/27/25 7:15PM
Pirates
Braves
+150
-178
+1.5 (-145)
-1.5 (+122)
O 8 (-110)
U 8 (-110)
Sep 27, 2025 7:16PM EDT
Texas Rangers
Cleveland Guardians
9/27/25 7:16PM
Rangers
Guardians
+122
-145
+1.5 (-190)
-1.5 (+158)
O 7 (-120)
U 7 (+100)
Sep 27, 2025 8:40PM EDT
Arizona Diamondbacks
San Diego Padres
9/27/25 8:40PM
Diamondbacks
Padres
+118
-140
+1.5 (-190)
-1.5 (+158)
O 7.5 (-115)
U 7.5 (-105)
Sep 27, 2025 9:39PM EDT
Houston Astros
Los Angeles Angels
9/27/25 9:39PM
Astros
Angels
-145
+122
-1.5 (+115)
+1.5 (-135)
O 9 (-110)
U 9 (-110)
Sep 27, 2025 9:41PM EDT
Los Angeles Dodgers
Seattle Mariners
9/27/25 9:41PM
Dodgers
Mariners
+110
-130
+1.5 (-205)
-1.5 (+170)
O 7 (-120)
U 7 (+100)
Sep 27, 2025 10:05PM EDT
Kansas City Royals
Oakland Athletics
9/27/25 10:05PM
Royals
Athletics
+100
-120
+1.5 (-195)
-1.5 (+162)
O 10 (-110)
U 10 (-110)

MLB Past Picks

Remi—our in-house AI—prices every game and prop using multi-season priors, tempo/efficiency, injury/usage signals, and market movement.
We publish fair prices, recommended “buy-to” numbers, and confidence so you can bet prices, not teams.

This preview covers Chicago White Sox White Sox vs. Chicago Cubs Cubs on May 17, 2025 at Wrigley Field.
Odds shown reflect widely available numbers and may update closer to kickoff.

Want more? Check live edges, player props, and line moves on our MLB odds pages, and compare prices before you place a bet.

    LEAN     %WIN     UNITS RESULT
NYM@CHC NYM -110 54.1% 3 WIN
HOU@ATH ATH +118 50.8% 4 WIN
NYM@CHC OVER 7 54.5% 3 WIN
STL@SF OVER 7.5 55.9% 5 LOSS
KC@LAA TYLER TOLBERT UNDER 1.5 BASES 54.4% 4 WIN
MIL@SD UNDER 9 54.7% 4 WIN
MIA@PHI KYLE SCHWARBER OVER 1.5 HITS+RUNS+RBIS 53.3% 3 WIN
WAS@NYM OVER 8.5 56.1% 6 LOSS
LAA@COL COL +108 50.5% 3 WIN
TOR@KC UNDER 9 54.7% 4 LOSS
SEA@KC KC +1.5 62.3% 5 LOSS
NYY@MIN OVER 9 55.1% 4 WIN
MIA@COL OVER 10.5 55.0% 4 WIN
MIA@COL AGUSTIN RAMIREZ OVER 1.5 HITS+RUNS+RBIS 54.3% 4 WIN
SEA@KC BOBBY WITT UNDER 0.5 SINGLES 54.4% 4 LOSS
PHI@LAD LAD -113 54.7% 4 LOSS
NYY@BOS OVER 7.5 54.3% 3 WIN
KC@PHI PHI -130 58.3% 4 WIN
LAD@SF OVER 7.5 54.7% 4 LOSS
NYM@PHI PHI -122 55.6% 4 WIN
KC@CLE KC -104 52.0% 3 WIN
CIN@SD JAKE CRONEWORTH OVER 0.5 HITS 53.1% 3 WIN
WAS@MIA MIA -123 55.2% 4 LOSS
LAA@KC UNDER 9.5 54.9% 3 WIN
TEX@ARI UNDER 9 54.2% 4 WIN
SF@COL UNDER 11.5 56.4% 6 LOSS
SF@COL RAFAEL DEVERS OVER 1.5 BASES 56.1% 6 WIN
MIA@WAS WAS -110 54.4% 4 WIN
NYM@DET OVER 8.5 54.5% 4 WIN
TEX@ARI UNDER 9.5 56.4% 6 WIN
TEX@ARI ALEJANDRO OSUNA UNDER 1.5 BASES 54.1% 4 LOSS
ATL@CHC CHC -116 55.1% 3 WIN
PHI@MIL OVER 8.5 55.0% 3 WIN
ARI@LAD SHOHEI OHTANI OVER 2.5 BASES 54.2% 4 WIN
SEA@CLE CLE +1.5 57.2% 3 WIN
CHC@SF CHC -105 54.1% 4 LOSS
NYY@CHW RYAN MCMAHON OVER 0.5 BASES 54.1% 4 WIN
PHI@NYM OVER 8.5 55.6% 4 LOSS
LAA@TEX LOGAN OHOPPE OVER 1.5 HITS+RUNS+RBIS 54.1% 4 LOSS
KC@CHW KC -109 54.2% 4 WIN
SD@SEA DYLAN CEASE OVER 16.5 OUTS 53.9% 3 LOSS
SD@SEA UNDER 8.5 54.4% 4 LOSS
MIN@TOR JOE RYAN UNDER 2.5 EARNED RUNS 54.1% 4 LOSS
SF@MIL MIL +100 54.0% 6 LOSS
TOR@MIA MIA +1.5 62.0% 6 WIN
CHC@LAA OVER 9.5 54.9% 4 LOSS
BOS@NYY CARLOS RODON UNDER 4.5 HITS ALLOWED 54.2% 4 WIN
KC@DET DET -115 56.1% 5 WIN
CHC@LAA LAA +1.5 57.6% 5 LOSS
CIN@ARI KEBRYAN HAYES STRIKEOUTS UNDER 0.5 56.2% 6 WIN
LAD@SD SD +110 50.9% 6 WIN