Moving from Illinois to Oregon
 

Moving from Illinois to Oregon. Does anyone have any tips on what time of year it may not be advisable to make this trip via moving truck due to weather and road conditions?

Mid-winter is often very rainy in Oregon west of the Cascades and of course, you'll have the opportunity for lots of snow if you go across on I-80 and parts of I-70. Mountain passes are particular touble areas in the winter. Fall would be a good time before the worst of the storms hit.

I think you should probably have made the move by mid-October at the latest to avoid bad weather on the mountain passes, but it could still snow then.

Most years we have a nice long Indian summer through October and into November. There will be periods of good weather still after that but you can get freezing and fog in some areas. Where are you moving to? Mostly always raining between mid Feb through May and into June.

Oregon is a big state. Have you decided on the wet side or the dry side? Do you or SO have a job lined up?
I've lived for 7 years now at 4400' elevation on the east side of the Cascades.
Is this a retirement move or a move to find new employment?