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