14U baseball tournaments near Chicago

6 upcoming tournaments within 50 miles.

Counts are teams already registered in each age division, straight from the organizer, rechecked twice a day. Distances are straight-line from Chicago.

• Sep 18–20 2026 PG Windy City Fall Classic PG · Wintrust Crossroads Sports Complex, New Lenox 314U · 31 mi
• Sep 19–20 Big League Dreams (MLB PLAYER RINGS) A-AA-Open USSSA · Crown Point 014U · 35 mi
• Oct 2–4 2026 PG Windy City Fall Frenzy PG · Wintrust Crossroads Sports Complex, New Lenox 114U · 31 mi
• Oct 9–11 2026 PG Windy City Fall Showdown PG · Wintrust Crossroads Sports Complex, New Lenox 114U · 31 mi
• Oct 16–18 2026 PG Windy City Fall Finale PG · Wintrust Crossroads Sports Complex, New Lenox 114U · 31 mi
• Oct 17–18 USSSA SPOOKY SLUGFEST (NEW EVENT CROWN POINT) USSSA · Crown Point 114U · 35 mi

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