Tokyo is 14 hours ahead of Chicago from mid-March to early November, and 15 hours the rest of the year.
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Quick reference
| CHICAGO | TOKYO · MID-MAR–EARLY NOV | TOKYO · REST OF YEAR |
|---|---|---|
| 9:00 am | 11:00 pm | 12:00 am next day |
| 12:00 pm | 2:00 am next day | 3:00 am next day |
| 3:00 pm | 5:00 am next day | 6:00 am next day |
| 6:00 pm | 8:00 am next day | 9:00 am next day |
| 9:00 pm | 11:00 am next day | 12:00 pm next day |
Questions
14 hours from mid-March to early November, while Chicago is on Central Daylight Time (CDT). 15 hours the rest of the year, while Chicago is on Central Standard Time (CST).
11pm from mid-March to early November, and 12am the next day the rest of the year.
Only Chicago. It moves to CDT (UTC-5) in mid-March and back to CST (UTC-6) in early November. Tokyo stays on Japan Standard Time (JST, UTC+9) all year.