Will skies be clear over southern Ontario Friday night?

It looks like skies will become clear during the evening as low-level cloudiness dissipates after sunset. Overnight, increasing moisture at jetstream levels may cause high clouds to appear over most regions. Over regions south of Georgian Bay and near or north of the GTA, increasing low-level moisture after midnight may cause increasing low-level clouds to develop.

Will skies be clear over southern Ontario Wednesday night?

Skies are likely to be mostly clear by sunset, except for diminishing patches of low-level clouds that could be visible over some southern regions. Gradually increasing jetstream-level moisture (illustrated below) may cause some high cloudiness to appear over some or most regions during the evening and increase by morning.

Skies are likely to become partly clear by sunset, but enough moisture will  remain over southern Ontario (illustrated below for mid-level moisture, but widespread low-level moisture may be more noticeable) to cause partly cloudy skies overnight over most regions.

Will skies be clear over southern Ontario Thursday night?

It looks like clear skies overnight, except for some continuing scattered high clouds especially during the early evening over regions close to Lake Ontario.

Will skies be clear over southern Ontario Wednesday night?

It looks like skies will have high-level clouds during the early evening, at least over regions near Lakes Erie and Ontario, and possibly over most regions of southern Ontario, due to a jetstream over southern Ontario (illustrated below over North America) and moisture along the jet especially over southern Ontario (illustrated below for early evening). Moisture may diminish overnight but may continue to cause visible high clouds over some or most regions.

Will skies be clear over southern Ontario Monday night?

It looks like lots of moisture will be present to cause at least partly cloudy skies, but breaks in the clouds may allow skies to appear partly clear especially during the early evening. Low and mid-level moisture is forecast to be least during early evening (mid-level moisture illustrated below for 700 hPa level) but jetstream-level moisture will most likely cause high thin clouds that will probably be easily visible in the bright Harvest moonlight.

Will skies be clear Sunday night over southern Ontario?
Partly clear and partly cloudy is the best description, with mid-level moisture moving northward across southern Ontario (illustrated below) but enough clear breaks may occur over most regions to allow the full (and eclipsed) moon to be occasionally visible.