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I love RoadTrips where the challenge is to avoid the obvious route(s) and take the road less traveled. In the Midwest and South this is particularly easy due to the wealth of four lane, divided highways that skirt the larger cities while offering bucolic scenery and access to some great rivers, lakes and forests. While there aren't a lot of designated scenic roads between Chicago and Cincinnati, it's easy enough to avoid Indianapolis and the Interstates without paying too big a time penalty. One such route would have you using I-65 south out of Gary for your final escape hatch from the Chicago metro area and then hopping on US-30 east to around Plymouth. There switch over to US-31 south. At Mexico, take old US-31 (marked as IN-190 around Mexico) to Peru where you'd pick up IN-19 south. Follow that to IN-18 east and IN-13 south to Lapel and IN-132 southeast to Pendleton. Next up is IN-9 south to US-40 east, the old National Road which you'd take to Cambridge City. There IN-1 will take you south to US-52 east into Cincinnati, duplexing with I-74 for your entry into the city.

AZBuck