Punta Cana is 1 hour ahead of Chicago. Punta Cana uses Atlantic Standard Time (AST, UTC-4) while Chicago uses Central Time (CST/CDT, UTC-6/-5). When it's 12:00 PM in Chicago, it's 1:00 PM in Punta Cana.
The Dominican Republic does not observe daylight saving time, while Chicago does. During US daylight saving time (March to November), both cities are on the same time.
Any time during business hours works! With only a 1-hour difference (or none during summer), you can easily coordinate calls during normal working hours.
Chicago O'Hare and Midway airports offer direct flights to Punta Cana, making it a popular winter escape destination for Midwesterners seeking Caribbean beaches.