• May 1 - Special Olympics
• May 7 - Oak Brook Pink 5K
• May 8 - Beverly Breast Cancer 5K
• May 10 - Kane County Cougars
• May 12 - Chicago Cubs
• May 14 - The ABTA Path to Progress 5K
• May 15 - The Chicago Spring Half Marathon
• May 21 - Greater Chicago Epilepsy 5K
• May 22 - Stepping Up To Wellness 5K
• May 28 - Arlington Race Track
• May 29 - Belmont and Sheffield Music Festival
• May 30 - Ridge Run
• May 30 - Fiesta de Mayo