Chicago is typically 15 hours behind Tokyo. When it's 3:00 PM in Tokyo, it's 12:00 AM (midnight) in Chicago. Japan does not observe daylight saving time, while Chicago does.
During US daylight saving time (mid-March to early November), the difference is 14 hours. During US standard time (November to March), it's 15 hours.
Optimal meeting window: 6:00 PM - 9:00 PM Chicago time (9:00 AM - 12:00 PM Tokyo next day). This catches morning business hours in Tokyo.
For evening calls to Tokyo, schedule 5:00 AM - 7:00 AM Chicago time (8:00 PM - 10:00 PM Tokyo same day).