Route 66 trip - May/June ‘21

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I’m seriously thinking of taking a Route 66 road trip this year, in May and/or June. I’d start in Chicago and then head west to Santa Monica.
Have any of you done this trip and if so do you have any observations you could share? I keep my bikes in Georgia, so I’d have to ride to Chicago from Atlanta first, and when done I’d ride back to Atlanta from California. I thought about shipping the bike to California, flying out to get it, and riding the route in reverse... but I’m not sure if that’s a smart idea or not. If I ride round trip, I’m thinking the trip would take 30 days, give or take, and would cover somewhere around 5000 miles. If I shipped it, I could save a week but the hassle seems a bit much. If anyone has done this ride, in any fashion, I’d love to hear your thoughts.

I've done part of it in a cage. I've been as far west as Springfield, MO on my CB1100. I'm not an expert, but I do know a fair bit about the Illinois portion. I'd be happy to provide a list of "should sees" and food stops for you if you'd like. I'd also be happy to meet you at the start and ride with you for the first bit, assuming that our schedules line up.