This past summer, @jppe cycled from Oregon to Boston, and found an [post=19048797]enjoyable route[/post] through Chicago to Gary Indiana and beyond. With that eastward direction in mind, may I suggest then turning North and riding in Michigan along the eastern Coast of Lake Michigan. This area is regarded as great for cycling,with some annual organized tours. This past fall, I drove from Grand Rapids to Traverse City, and the area is not too urbanized and traffic was light. It is however a popular tourist destination in the summer.
You could ride North and then double back to Chicago, or take a ferry from Ludington, MI across the Lake to MIlwaukee, and then ride back to Chicago through Wisconsin. BF subscriber @Irwin 7638 is an active cyclist in western Michigan, out of Kalamazoo.
BTW I’ve had this problem with posting links from my computer since the programming change back in June. jppe's post about Chicago is on the Fifty-Plus Foum, last reply on September 13: Chicago.....AND Gary in the Rear View Mirror!!.
Last edited by Jim from Boston; 11-24-16 at 05:30 AM.