All Diagonals - Dubi
A.K.A. the "not straight" route, maybe add boystown.
Mosaics. - Andrew
Underpass at Hollywood, underpass at Foster, wall at 4730 N Sheridan, various downtown?
Alphabetical - Susan Levin
26 sequential points of interest, can be literal (street names), navigational (L,R,route forms a letter), loose (billboard contents), social ("Mmmmmmmm"), conceptual (end = "Zzzzz") ...
Madonna - Dubi
All virgin pavement. Like a virgin, get it?
Lots of blissfully new asphalt in my neighborhood lately.