Best Known Road: Blackjack Road (shown)
Running between Galena and Savanna, Illinois, Blackjack Road is really a collection of various highways, and it’s got tons of twisty bits to keep you entertained. When you get to Savanna, Poopy’s is a legendary biker bar-slash-tattoo parlor that’s worth checking out.
Lesser Known Road: Highways 144 and 28 to Sheboygan
Ask any Chicagoan (we did) and they’ll all tell you the best roads near Chicago are in Wisconsin or Michigan. Fortunately, Wisconsin and Michigan aren’t that far, and if you take 144 and 28 up to Sheboygan, you’re rewarded with plenty of curves over rolling hills, and on the way back you’ve got lake Michigan right next to you the whole way down.
Best Known Road: Tail of the Dragon (shown)
With over 300 turns in fewer than 10 miles, no turn offs between the start and the finish, Deals Gap, otherwise known as Tail of the Dragon, is a mecca for any proper gearhead. It does get somewhat full of like-minded individuals, though, so you’ve got to know the right times to go to avoid traffic, but it’s worth the research.