Cadler - You haven't offered much info to go on - when, your experience, etc.
First, it's usually easier to connect up with other riders who are low-budget, camping than people who are doing motels. The former tend to be more casual in plans, the latter more specific.
There are a number of designated cycling routes or other similar mapped routes. The Lincoln Highway, the first transcontinental highway, has many older sections with very little traffic.
There are excellent strip maps of the old Lincoln Highway in Ohio at this website:
http://www.lincolnhighwayoh.com/guide/preface.htmlTricky east of Canton, great west all the way to Indiana border.
Make sure to zig off the Lincoln Highway to Monroeville, Indiana - best cycling hospitality in the Midwest.
(Plus the stretch of 4-lane Lincoln Highway makes cycling tough.)
Indiana also has strip maps for the Lincoln Highway:
http://www.lincolnhighwayoh.com/articles/8-articles/34-in-search-of-the-1928-lincoln-highway-in-indianaThe 1928 route goes thru Columbia City, Warsaw and Plymouth - towns that have nice camping.
(The link to eastern half is wrong -
http://www.lincolnhighwayoh.com/images/Indiana/1301_001.pdf)
From Plymouth it gets trickier. You might want to head NW to Michigan City and the lake.
Nice rail trails in NW Indiana -
http://www.greenwaysfoundation.org/trails.htmlThat take you to the edge of Chitown.
Backtracking:
Pennsylvania also has a number of designated bike routes with strip maps -
ftp://ftp.dot.state.pa.us/public/pdf/bikes/bicyclepa.pdfhttp://www.dot.state.pa.us/Internet/Bureaus/pdBikePed.nsf/BikePedHomepage?openframeset&Frame=main&src=InfoBicycleInformation?readformRoute V generally parallels I-80 from the Ohio border to New Jersey.
Route S follows much of the Lincoln Highway - would need to cut thru Pittsburgh on rail trails to connect.
Route Y is in areas of Penna with the least traffic and most parkland.
All have clickable strip maps.
Have a safe trip - J