Thanks once again to OAV014 Mal for this contribution.
This GA VFR tour is somewhat unusual (and interesting) as it operates on two levels:

At the top level we have the overall flight plan............."It winds from Chicago to LA....."    - .KMDW to KLAX. 
However, each leg can be subdivided into short segments which visit airports along the route and hence give opportunities for touch and goes or sight seeing on the way. This, of course is entirely optional.
In addition to the overall flight plan, an optional route for each individual leg is included below for those pilots who wish to use them. These are labelled 1 to 10 below.

Finally, for those pilots who like to sing in the cockpit, here is a link to The Rolling Stones version of the song - Route 66 - YouTube  & the lyrics - The Rolling Stones - Route 66 Lyrics | AZLyrics.com

10 legs, 1689nm total, average leg length 170nm.

1. KMDW 0C3 KDTG KBMI KSPI KSTL

2. KSTL KUUV KUBX KTBN KSGF

3. KSGF 2MO KJLN H04 KTUL

4. KTUL KSUD KOKC

5. KOKC KOJA 2F1 KAMA

6. KAMA E52 KTCC KSXU 0E0 KABQ

7. KABQ NM74 KGUP

8. KGUP 85V P10 T03 KGCN

9. KGCN 1G4 KLAS

10. KLAS 0O2 KDAG L26 KPOC KLAX