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Left: Chicago Cubs’ Alex Bregman advances to third base on a double by Ian Happ during the first inning of a baseball game against the Cincinnati Reds, Sunday, Sept. 20, 2026, in Cincinnati. (AP Photo / Kareem Elgazzar) Right: Chicago White Sox’s Miguel Vargas hits an RBI single during the second inning of a baseball game against the Kansas City Royals, Thursday, Sept. 24, 2026, in Kansas City, Mo. (AP Photo / Charlie Riedel)

Cubs and White Sox Reached the Playoffs. Here’s What to Expect in the Wild Card Series

Sep 28, 2026 | Shelby Hawkins

This marks the first time since 2020 that both Chicago teams made the postseason. Both teams will play their best-of-three Wild Card Series on the road starting Tuesday with the Cubs taking on the Padres in San Diego and the White Sox facing the Astros in Houston.