You can see Vancouver from Neck Point Park, Nanaimo: about 60km distance? I took a few photos maybe I'll post them sometime.
I was surprised how quickly Winnipeg fades from view. You can see several downtown towers from Dugald, about 24km distance.
This past Saturday, on my way to Toronto I drove through Limehouse and Glen Williams, noticing you can see Mississauga City Centre from the Limehouse Presbyterian Church parking lot:
https://imgur.com/a/MqgVPjl
You'll have to zoom in between the tree and leftside of the church.