2018 maybe?

In 2018 I was planning on doing Route 66 end to end (Chicago to Los Angeles). It's 2,000 miles and I thought it would be a fantastic achievement as well as a thrilling ride.
However, when I read reviews there are so many people who are so dissapointed, not much of the original route left and what there is has been so commercialised it just isn't authentic. There are bits that are genuine but when I checked what it would cost, flights, bike hire, guided tour (which means a support vehicle for a group of riders) etc. it came out at £8,000. Unless I win the lottery there's not much chance of me doing that.
So my Brother in Law, who lives in Chicago, suggested I fly over there, hire a bike and ride around. He knows some great rides around Ohio, Wisconsin, Michigan, and could accompany me.
Great idea but why not do the lot by a round trip of Lake Michigan, stopping off for a night or two in interesting places to visit Milwaukee (HD Museum) Oshkosh Aviation Museum, and other places on the route. Looks like there would be some stunning scenery too.
Plenty of time to plan it but it would be a fraction of the price, I guess around £2,500 including flights, Bike hire, petrol (sorry, that should be 'Gas) accommodation, food and sundry spending money.
Sounds like a plan.