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No real reason to bypass the entire area. You don't even come close "the south side" by taking 55 to 80 and shooting across to to Indiana.
But if you're looking for a nicer place to spend the night, you should head out on 70 from STL and catch 57 up to Champaign IL. Spend the night there, nice college town where U of I is located. Then take 57 north a ways and cut across on a rural interstate to 65 north in Indiana. By the time you hit 80 to continue heading east, you will have bypassed the most congested areas of the IL/IN border.
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