Last week I did a 41 miler from a relative's home in South Elgin to Downtown Chicago.
Previous night we had a terrible & destructive storm. The first 20 miles into the Great Western Path had quite a few fallen trees accross it so I had to dismount & climb with my cross rig over my shoulder, for a second I felt like I was racing (hehe). This is a converted old railroad bed, secenery's simply gorgeous, lots of wild life.

The rest was over streets, fell one time under a bridge in Oak Park due to slippery tracks/old brick pavers. It took me 2.5 hrs, had to leave at 5:45 am.
Definitely something I don't want to do it everyday, as nice as it is..