We’ve had on and off discussions about a bike route between Chicago and South Bend, yet as far as I know, no one has actually mapped and made available a complete route.
Accordingly, I was excited to hear about an organized ride between Millenium Park in downtown Chicago to Indiana Dunes National Lake Shore and then on to Warren Dunes State Park over two days. The ride is Le Tour de Shore, and participation has been growing steadily in this charity ride since the inaugural voyage in 2004.
Click the above link to the official ride website for more details; there you can also view a route map (both a PDF version and an online interactive version). Although Warren Dunes is too far north for a direct ride between South Bend and Chicago, their route gets one around Gary, which I suspect is the biggest challenge for such a ride. And, once east of Gary I don’t think it would be hard to find a safe yet more direct route to South Bend.
I hope to join the ride this year, and my intention is to then map out and try a complete ride from Chicago to South Bend (unless Adam Bee beats me to it.. perhaps he already has?).