Pretty much all of our public accessed land is very limited as far as any challenge and in my opinion you have to just appreciate it for the occasional scenic vistas on high bluffs overlooking river basins and remote lakes, etc.
Your closest from Chicago would be up the coast, hway31 north up thru Muskegon to the Russell road exit and then up into the national forest area north of Blue Lake.
I just checked out this area last weekend to see what all the trail closures were.
I'm not familiar with what good stuff had been cut off, but there is still plenty of spots for scenery, especially after it greens up some.
As a general guide, stick to the trails with the 4 digit posts in the NF, seasonal roads,
and on state land stick to the ORV routes(designated for full width), which are both rare and lame. Power/utility lines are off limits, as well as stream beds, marshes etc. Basically you stick to what granny could go down in 2wd in the Buick.
The Baldwin NF ranger station will have the maps detailing what's left there. You'll find they're pretty much meant to be a go along guide with another map, especially with no familiarity with the area, as there is not much detail.
The DNR site has maps of the state trails, and if heading into trails east of Baldwin, expect heavily whooped out, tiresome wheeling until you get a ways off 37.
Don't forget the Silver Lake sand dunes and private parks are popping up.