The recent jump comes amid continued geopolitical unrest and in spite of a government report that showed the biggest on-week gain in inventories in more than a decade, typically a bearish sign for oil.
So how high will crude go? And what does that mean for stocks?
"Oil is one of those places where it's feast or famine. Either there's really tight supply [or] tremendous demand, which is the last two years," said Gina Sanchez, CNBC contributor and founder of Chantico Global. "This year we are expecting quite a bit of supply to come online, so that should depress oil prices."
But despite an abundance of supply, Sanchez believes geopolitical and social unrest will outweigh any supply demand issues. "I do think that the fat tail risk on oil suggests that the chances of higher oil are quite high."
The charts are bullish too.
Rich Ross of Auerbach Grayson says oil has reached a key inflection point, and if it can move just a little bit higher, it will break through the key $105 level and be off to the races. But the key to a sustained move, as he sees it, will require patience.
"I don't recommend chasing crude oil here. Every time you see a move up they seem to pull the rug out from underneath you," cautioned Ross. "I think we are set up for a disappointment in the short term, even though the backdrop still looks bullish for crude oil. I would be a better buyer on a pullback."
So what will it mean for stocks? Check out the video for the full discussion with Ross and Sanchez.