Nest the tooltip’s style within the checkbox’s style as follows:
<Window.Resources>
<Style TargetType='CheckBox'>
<Style.Resources>
<Style TargetType='ToolTip'>
<Setter Property='Background' Value='Red'/>
</Style>
</Style.Resources>
<Setter Property='FontSize' Value='14'/>
</Style>
</Window.Resources>
<Grid>
<CheckBox ToolTip='Sample ToolTip!'>Sample CheckBox</CheckBox>
</Grid>
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