Sydney is 15, 16 or 17 hours ahead of Chicago, depending on the time of year.
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Quick reference
| CHICAGO | SYDNEY · EARLY NOV–MID-MAR | SYDNEY · EARLY APR–EARLY OCT | SYDNEY · IN BETWEEN |
|---|---|---|---|
| 9:00 am | 2:00 am next day | 12:00 am next day | 1:00 am next day |
| 12:00 pm | 5:00 am next day | 3:00 am next day | 4:00 am next day |
| 3:00 pm | 8:00 am next day | 6:00 am next day | 7:00 am next day |
| 6:00 pm | 11:00 am next day | 9:00 am next day | 10:00 am next day |
| 9:00 pm | 2:00 pm next day | 12:00 pm next day | 1:00 pm next day |
Questions
17 hours from early November to mid-March, 15 hours from early April to early October, and 16 hours in between (mid-March to early April, and early October to early November).
2am the next day from early November to mid-March, 12am the next day from early April to early October, and 1am the next day in between (mid-March to early April, and early October to early November).
Yes, both, on different dates. Chicago moves to CDT (UTC-5) in mid-March and back to CST (UTC-6) in early November; Sydney moves to AEDT (UTC+11) in early October and back to AEST (UTC+10) in early April.