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How about I-94 out of St. Paul southeast to I-39 south to bypass Chicago down to I-74 East (actually southeastly) to I-65 south to Louisville? This is less than a 750 mile trip.
This avoids Chicago but I-74 does skirt the southwest outside part of Indianapolis. I wouldn't want to drive Chicago either, but Indianapolis is not as bad.
I'm assuming you meant Louisville, KY. Will this work?
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