After 3 years of planning, I am riding Route 66 starting June 8

[tntnj]

+1 on weather for temperature in the deserts. We left Flagstaff, AZ, in late June: it was lower 50's. By the time we reached the Colorado River, crossing on I40 down the mountain from Kingman, AZ, that day, it was 110°F! At 200-300 miles a day, you should be able to avoid mid-day riding.

Have an enjoyable and memorable adventure!

I am aw

NJ to the head of Rt66 in Chicago is ~12-14 hours (800 mi) of saddle time.
It is doable in 1 day but your pace looks like you may need to plan a 2nd day to Chitown.
BTW, I have that route all mapped in GPX segments if interested. You can drop in your POIs along the way.

I am thinking of driving to South Bend -Gary IN for the first stop Then to Chicago the second day.
I think you sent me those but I could not get base camp to load and view on the Garmin GPS