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Planning a California Trip - looking for advice on 2 things

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My wife and I are thinking about heading out to California this summer. We both have not been out there together so we are excited.

We will likely be flying out of Grand Rapids, MI or Chicago and into LAX where we will rent a car. We are planning on staying with some friends for a few days in LA then heading up to San Francisco along the coast, stay a few nights in SF. Then we would make our way up to Portland, OR staying a night around Crater Lake on the way.

Those are the main things we would like to see with some variation of the above.

Here's the challenge:
The plane ticket cost for doing a multi-city flight GRR-LAX-PDX-GRR makes sense, although the price of a multi-city car rental is huge. It is not worth the expense. It would make more sense for us to drive up to Portland and then drive all the way back to LA and fly out again when you look at time/cost. We would rather not make the drive back however. Does anyone have any advice on this? Is there a different route, where we can drive back to LA on a limited budget? Multi-city car rental advice?

Also, ticket prices from the Midwest to Cali are really great right now but had a slight spike in the last few days. I checked to see how full the planes were and they were very empty. Should we jump on these tickets now out of fear of the increase, or should we wait until they head back down again?

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