DH DTW-MEM-TUP-MSL

Overnight

Fly MSL-TUP-MEM

DH MEM-DTW

I've done a variation of that a couple of times.

Or:

DH DTW-CWA

Fly CWA-MSP

Scheduled 2-minute connection to make a DH back to DTW, didn't make it, had to wait a few more hours for the next flight... only to find out that the CA I was filling in for was DH'd to DTW to cover something... which is where I was to begin with.