That layover works too, but the price is still not as cheap as point-beyond ticketing. The itinerary I posted is only $168 (with a Saturday stay, which is what I always do)... half the price.
But if there is a high risk of getting caught (hence my open question to forum members) then it's definitely not worth it. A change to MSP-DTW (no extra segment), then DTW-MSP-CHI increases the price by $90, but would be usable at least the first time.