2026 Labor Day Tournament

Chicagoland Roy Hobbs Baseball

2026 Labor Day Baseball Classic

50+ Division | September 5-7, 2026

Tournament Overview

📍 Location Wintrust Cross Roads Sports Complex
New Lenox, Illinois
📅 Dates September 5-7, 2026
4 Games Guaranteed
💰 Entry Fee $1,800 per team (up to 15 players)
$25 per additional player (max 20)
🏆 Age Division 50+ (must be 50 by 12/31/2026)
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Tournament Information

Format

Pool play consists of 3 games, followed by playoffs and championship games:

  • 2 pool games on Saturday, September 5th
  • 1 pool game on Sunday, September 6th
  • Quarterfinal Playoffs on Sunday, September 6th
  • Semi-finals and Championship on Monday, September 7th

Awards

Team Championship Award: Commemorative World Series Team Trophy

Championship Team Bonus: $500 discount off 2027 tournament

Individual Champions: Championship medals

Runner-Up Team: Second place medals

Championship Game MVP: MVP award

Team MVP: Award for each team to present to a player at tournament end

Entry Fee: $1,800 per team

Up to 15 players included | $25 per additional player (maximum 20 on roster)

What's Included:

  • 4 games (includes first playoff game)
  • Play on full-size, all-turf baseball fields
  • Two umpires per game
  • Game baseballs
  • Playoffs and championship games
  • Awards for team champions and runner-ups
  • Commemorative t-shirt
  • Lineup cards and scorebooks

Payment Schedule

Deposit Due: May 30th, 2026
$500 non-refundable deposit to reserve your spot

Balance Due: August 8th, 2026
Final payment must be submitted

Teams not submitting deposits by May 30th will be accepted on a first-come, first-served basis.

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Tournament Schedule

Friday, September 4th

Team Check-in: 5:00 PM - 7:00 PM

7:00 PM - Opening Night Celebration

  • Bar opens
  • Music
  • Complimentary hors d'oeuvres

Saturday, September 5th

Team Check-in: 8:00 AM - 11:00 AM

  • 10:00 AM - Pool Play Game 1
  • 1:00 PM - Pool Play Game 2

Sunday, September 6th

Team Check-in: 8:00 AM - 11:00 AM

  • 10:00 AM - Pool Play Game 3
  • 1:00 PM - Quarterfinal Games (Single Elimination)

Monday, September 7th

  • 10:00 AM - Semi-Finals
  • 1:00 PM - CHAMPIONSHIP GAME

Note: All times are weather dependent and subject to change. Please check the tournament website for the most up-to-date information.

All playoff games are single elimination.

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Tournament Requirements

All teams must be in compliance with all park, facility, and city guidelines, policies, rules, and ordinances.

Required Documents (Before Tournament Begins):

Deadline: August 6th, 2026

  • Team Roster
    • Any number of players over 15 requires additional charge of $25 per player (16-20 max)
    • Roster must be finalized by August 6th
  • Team Registration Form
    • Must be completed with all fees paid
  • Player Registration Form
    • All players must be registered by August 6th, 2026
  • Player Age Verifications
    • Documentation required for 50+ division eligibility
  • Signed Player Waivers
    • Required for all roster players

Important: Teams will not be permitted to play without all required documentation submitted by the deadline.

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Tournament Rules

Tournament rules will be posted here soon.

Please check back for detailed rules and regulations, or contact us with any questions.

For questions about rules, please contact:

Email: spaschka@gmail.com

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Hotels & Lodging

We've partnered with several nearby hotels offering convenient access to Wintrust Cross Roads Sports Complex in New Lenox. Contact hotels directly to inquire about availability and rates.

Holiday Inn Express

Address: 19220 Greenwich Dr., Mokena, IL 60448

Phone: (708) 390-6200 Ext. 151

Fax: (708) 864-4697

Contact: Rosa Espinoza (Area Manager) - rosa.espinoza@ighospitality.com

Contact: Bryanne Rasmussen (Sales Manager)

Current Rooms Available: 84

Hilton Garden Inn Chicago/Tinley Park

Address: 18335 S. La Grange Rd., Tinley Park, IL 60487

Phone: (708) 429-2266

Fax: (708) 429-2277

Contact: Kelly Stergiopoulos (Director of Sales) - Kelly.Stergiopoulos@Hilton.com

Website: hgl.com

Rooms Available

Country Inn & Suites by Radisson / Tinley Park

Address: 18315 S. La Grange Rd., Tinley Park, IL 60487

Phone: (708) 560-9300

Contact: Monty Patel (General Manager) - monty.patel@hawkeyehotels.com

Website: choicehotels.com/722

Rooms Available

Homewood Suites by Hilton / Orland Park

Address: 16245 S. La Grange Rd., Orland Park, IL 60467

Phone: (708) 364-9411

Main Line: (708) 645-5497

Contact: Darryl Thomas - darryl.thomas@hilton.com

Website: www.OrlandPark.HomewoodSuites.com

Rooms Available

Holiday Inn Chicago Tinley Park

Address: 18320 N. Creek Dr., Tinley Park, IL 60477

Phone: (708) 840-4300

Contact: Lauren Terry (Director of Sales) - sales@sdhotelsllc.com

Some Rooms Still Available

Sleep Inn

Address: 18420 Spring Creek Rd., Tinley Park, IL 60477

Phone: (708) 342-1700

Fax: (708) 342-1709

Contact: Jatin Patel (General Manager)

Email: jaynilkanthllc@gmail.com

Mobile: (630) 827-1898

Rooms Available

Booking Tips:

  • Mention "Chicagoland Roy Hobbs Baseball Tournament" when booking
  • Book early as rooms fill up quickly during tournament weekend
  • Contact hotels directly for best rates and availability
  • Most hotels are within 10-15 minutes of the tournament venue