| 12:00 p.m. - 7:00 p.m. | Friday, September 27 | Health Way of Life Expo | Packet Pick Up | Roosevelt Collection |
| 6:00 p.m. | Friday, September 27 | Shake Out Run | Healthy Way of Life Expo | Roosevelt Collection |
| 10:00 a.m. – 5:00 p.m. | Saturday, September 28 | Health Way of Life Expo | Packet Pickup | Roosevelt Collection |
| 4:45 a.m. | Sunday, September 29 | Shuttles Begin to Depart | Millennium Park & Belmont "L" Station locations |
| 5:00 a.m. | | Gear Check & Will Call Open | Jackson Park |
| 5:00 a.m. | | Last Shuttles Depart | Millenium Park & Belmont "L" Station locations |
| 6:00 a.m. | | Lake Shore Drive Closes | Between 31st and 67th Streets |
| 6:45 a.m. | | Half Marathon Corrals Close | Cornell Avenue, just north of Hayes Drive |
| 6:45 a.m. | | Wheelchair/AWD Start | Half Marathon | |
| 7:00 a.m. | | Chicago Half Marathon Start | |
| 7:35 a.m. | | Wheelchair/AWD Start | 5K | |
| 7:45 a.m. | | 5K Start | |
| 8:00 a.m. | | Finish Festival Opens | Jackson Park |
| 8:45 a.m. | | Awards Ceremony | Main Stage | Finish Festival |
| 11:30 a.m. | | Finish Line Closes | |
| 12:00 p.m. | | Finish Festival and Gear Check Closes | |
| | Last Shuttle departs Jackson Park | |
