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Chicago to Badlands - interesting stopovers, etc?

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In the early stages of planning a road trip. Our starting and ending point is Canada - southern Ontario - but will head to Chicago for a few days first then on to Badlands National Park. Any thoughts on some sights/destinations in between? Timing: early to mid June. Would if possible prefer every leg of this trip to have something interesting worth travelling to, even if a little out of the way, would like more than just a roadside hotel with a bed for the night, and don't want marathon drives every day. After Badlands will head up to Theodore Roosevelt in ND and then possibly to Grasslands National Park in Saskatchewan, Canada before heading gradually home (although we may save the last for another trip in which case I'll be looking for another interesting route home). So any other insights to that general section of North America would be welcomed. We are active mid-aged, no kids, love nature, scenery, birdwatching, light to moderate hiking, interesting small towns and good food.

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