It has been quite a few years since the discussion on routes has been posted.  I am looking for a route on paved roads or trails from Chicago to Madison to spread out over 2-3 days. Gravel might be okay depending on how rough it is.  One bike on the ride has 23 mm tires without enough clearance to go much wider.  Any suggestions?

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I've done Chicago to Milwaukee several times, never done Milwaukee to Madison.  Milwaukee is pretty much the half way point.  The route is mostly trails, though not entirely.  I mostly followed the Google Maps route though added a little distance by trying to stay as close to the lake as possible.  Of course you can also ride northwest through the northwest suburbs and stick to mostly roads.  I did the Harvard to Madison route a few years back and it was mostly on low traffic routes, though of course this route has you going up and down hills most the entire way.

+1 I've gone Chicago to Milwaukee and Milwaukee to Madison - along the Glacial Drumlin Trail - just make sure you buy the trail pass, it's cheap, but there were rangers ticketing some other bikers along the way

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