Short for chill session. Describes any amount of time spent with 1 or more people, although usually not large groups. A chillsesh is typically either last-minute or unofficially planned, and sometimes completely spontaneous. Because of this, a chillsesh can last anywhere from half an hour to several hours.
"Me and Jim were just walking around town and ran into Sarah, so we ended up having a chillsesh for a little while."
"Hey, you doin anything after school?"
"Nah."
"Chillsesh at my house?"
"Sounds good."
"So did you end up hanging out with her?"
"We didn't really hang out. We just had like a one-hour chillsesh, but then she had to go."