2027 Hill of a Race Obstacle Run

Race Information

The Hill of a Race Obstacle Run offers the Endurance Challenge, Competitive Men & Women, Master's (40+) and ten Recreation waves all awaiting you, your family, and friends!

See how far you can go with the Hill of a Race Endurance Challenge! Participants will push themselves through multiple laps of the course during the race window. Winner will be determined by total laps completed. Endurance Challenge participants will be allowed to skip to the front of the obstacle lines while running through the Recreational waves.

👍 Run Pick of the Month: SKECHERS Hot Chocolate Run – Chicago

📍Chicago - Sunday November 1, 2026

💸 Get a free tumbler. Use Code RGCHI

😄 Why We Like This Run
✅ Exclusive SKECHERS Hot Chocolate Run Fleece
✅ Chocolate Fondue Finisher’s Mug
✅ Free Race Photos

Ready for "America’s Sweetest Race"? Join thousands of runners in the heart of Chicago for the iconic SKECHERS Hot Chocolate Run! Whether you’re tackling the 5K, 10K, or the signature 15K, every mile is fueled by fun and every finish line is paved with chocolate.

Bring your friends, bring your family, and get ready to earn that cocoa - because there’s truly no finish line sweeter than this one. Sign up now and prepare to indulge!

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