Dual sport riders from the Chicago area typically have a hard time finding good places to ride. I have found some nice unpaved country roads and trails through the woods in Allegan County, Michigan, about a two hour ride from Chicago. From Chicago, this trip can easily be a day trip, out and back, or an overnight trip using any of the nice hotels or B & Bs in the area, or even camping if one desires.
The roads and trails pictured here are in and around the Allegan State Game Area in Allegan, Michigan. The area is a 40,000 acre game preserve that is used for hunting depending on the season, so I would not recommend riding the trails during any hunting season, generally which start late fall.
Getting there from Chicago can be done on any number of roads, but you will want to get yourself to Glenn, Michigan to be close to the trails. Glenn is located about two hours from Chicago on Blue Star Highway at 114th Street, on Michigan's west coast. Glenn is a charming little town in itself. Good food can be had at The Glenn, the local restaurant, which is a biker's favorite on summer weekends. Or hit the Full Belly Deli located in The Glenn Store
across the street
Ride east out of Glenn on 114th Street until 66th Street. Turn left and ride north to 116th. street. A right on 116th will point you east toward the dirt roads and trails.
About mile down the road, you will be inspired by this road sign:
With very little exception, the roads will be gravel, like this:
The roads might be straight and flat, but at least they're not paved!
Follow 116th east until the road narrows and becomes a one-lane road. Around 46th Street you can take any of the trails to the left or right of the road. Avoid anything marked no motorized vehicles. Most of the trails are wide enough for a car, although some narrow down to single track. They are dirt or packed sand in most areas, although softer, deeper sand can be encountered along with some muddy areas. I have ridden a large portion of the trails on both my R1200GS and KLR650, both of which easily handled the conditions.
Here is one of the sandier trails:
If you plan to camp, the Ely Lake Campground offers primitive, but nice, camp sites.
The area has many well-marked snowmobile trails.
This nice trail through the woods started wide and got down to single track.
Riding the trails can be a multi-hour affair if you so desire. At the end of the day, a stop along the beach in Glenn offers superb views.