| Time | Mileage | |
| 8:25 AM | 2986 | Start: South Bend, IN |
| City streets, US 31, US 20 around South Bend | ||
| 9:03 AM | 3002 | Fuel: Speedway, South Bend |
| I-80/90 West | ||
| 9:21 AM EST/CDT | 3015 | Entered Central Time Zone, but the time stayed the same |
| I-90 West | ||
| 10:18 AM | 3077 | Entered Illinois |
| US 41, Lake Shore Drive North | ||
| 10:40 AM | 3093 | Parking in Chicago at the lakefront |
| City streets | ||
| 3102 | Parking near Wrigley Field | |
| City streets | ||
| I-90 East | ||
| I-55 South | ||
| Local streets near Lemont | ||
| 6:36 PM | 3139 | End: Lemont, IL |
Day 2 Mileage: 153 miles, total so far: 965 miles..