I went to u of o.
It is 1.2hrs to the closest hill, Willamette Pass which has a small park and on good cold pow days the terrain is really sick if you know where to go.
The next closest hill is Hoodoo, has a small park and usually a little warmer there. 1.75hrs away.
Mt Hood is 3 hours away, I had friends who went there and would stay in hood river.
Mt Bachelor on a good drive is about 2.5hrs away. Thats where I went most weekends all 4 years. The only problem is rides. if you have a car or have friends that are always trying to go and you split gas, you can make it happen. senior year I got up mostly everyweekend. I found people I knew in Bend and would go up for the weekend to make the drive worthit. I planned fridays off in my schedule so I would go up thursday night to bend and stay fri-sun.
There is a snow club (Snowboard + Ski) at u of o. They take vans up to mt bachelor as well.
If you are trying to go ski every day of the week, I would go to OSU/UO cascades or COCC, community college in Bend. I have friends there and they got to ski every good pow day while I sat in class during the week.
They mostly come at night, mostly..