Toronto is 1 hour ahead of Chicago all year.
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Quick reference
| CHICAGO | TORONTO · ALL YEAR |
|---|---|
| 9:00 am | 10:00 am |
| 12:00 pm | 1:00 pm |
| 3:00 pm | 4:00 pm |
| 6:00 pm | 7:00 pm |
| 9:00 pm | 10:00 pm |
Questions
Yes, all year. Both change their clocks on the same dates, so the difference stays 1 hour.
10am, all year.
Yes, both, on the same dates: Chicago moves to CDT (UTC-5) and Toronto to EDT (UTC-4) in mid-March, and both move back in early November.