Milan is 7 hours ahead of Chicago. Put the other way round: Chicago is 7 hours behind Milan.
Chicago is UTC-5 in summer and UTC-6 in winter; Milan is UTC+2 and UTC+1.
Working 09:00 to 17:00 in both cities leaves 1 hour in common: 09:00 to 10:00 in Chicago, which is 16:00 to 17:00 in Milan. Those are the hours to aim a call at.
Both cities move their clocks for summer, and by the same hour, so the gap above holds for almost the whole year. It slips by an hour for the days between the two countries' switch dates, which do not line up exactly.
| Chicago | Milan |
|---|---|
| 08:00 | 15:00 |
| 09:00 | 16:00 |
| 10:00 | 17:00 |
| 11:00 | 18:00 |
| 12:00 | 19:00 |
| 13:00 | 20:00 |
| 14:00 | 21:00 |
| 15:00 | 22:00 |
| 16:00 | 23:00 |
| 17:00 | 00:00 next day |
| 18:00 | 01:00 next day |
This page covers one pair. TimeGap takes a list: add every city you care about, drag one marker, and every row reads the same instant on its own clock. It marks the hours you would actually take a call, finds the window where the most people are reachable, flags public holidays, and puts the time you pick straight into Outlook or Google Calendar.