I tried searching this but the terms are too common...

IN the next 6 weeks I'll have _several_ days where I'll leave in the morning, do a job in one city continue on (on the same itinerary cause I didn't think about this until now) and do another job in another city. An example would be CVG-CLT-ORD in the morning then ORD-CLT that night returning CLT-CVG the next morning.

Since these flights are on the same itinerary will the bags be dropped off at baggage claim in ORD, stay in the baggage system until the evening arrival back in CLT, or will they just stay put in CLT after the first arrival?

One of the GA's here could give a more official answer, but I'd venture it depends on what you tell the agent when you check your bag - I'm assuming from the question that you will be checking a bag.

If you need your bag in ORD & CLT, just explain that to the agent and have them tag it appropriately - CVG/CLT/ORD when you initially check in, ORD/CLT the second, and CLT/CVG the third.

Of course, that means you'll have to visit the ticket counter each time.

Jim