Distance: 77 miles
Route: TCX / GPX
Ride time: 3.5-4.5 hour
At just over an hour's drive northeast of Chicago is, arguably, the best rolling terrain to ride within a day's drive of the city. This route is comprised of the Indiana-portion of the famous autumn race, The Apple Cider Century. It's a lush, rolling ride on well-manicured roads with very little traffic.
It's easy to shorten the route down, or to stretch out back into Michigan. It's also in excellent proximity to Sawyer, Michigan which is home to Greenbush Brewery - a great place for post-ride libations and excellent food (there's also Infusco Coffee right up the block serving some good espresso).