The remainder of the weekend will stay quiet. Temperatures will start off cool Sunday morning but a southwest wind will boost afternoon highs back into the low to middle 50s. Very strong high pressure will move into the Great Lakes Sunday night pushing a weak cold front through southern Wisconsin and northern Illinois Monday morning. Winds will turn more northeast Monday and Tuesday keeping temperatures a little cooler than Sunday's readings.
Meanwhile, low pressure will begin to develop in the central Plains pulling a warm front through Wednesday. A combination of southerly winds from high pressure and the low in the Plains will bring a decent amount of Gulf moisture northward Wednesday and Thursday. A few upper level disturbances riding along the warm front could cause a couple light showers Tuesday, but the biggest threat for rain will arrive late Wednesday and Thursday. Rainfall amounts of 1"-2" could be possible by the time the system moves into the Northeast Friday afternoon. Unfortunately, it does look like Halloween will be rainy, and possibly stormy, if enough instability develops in the atmosphere.
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