is it possible to drive from detroit,MI to chicago,IL and back to detroit in 1 day

I'd say no. Chicago has traffic that can derail a clock. If you do it night maybe.

 

It can work only once in a while, not on a regular basis

 

Then your plan should include a significant amount of wasted time since it's unreasonable to expect all 4 customers are going to behave like a NASCAR pit crew to load/unload you, also brokers are famous for saying "Chicago" and meaning Aurora, IL or "Deeetroit" and meaning Royal Oak, MI.

 

No way.

 

No idea, I pull a van. Flatbeding looks like too much work for me

 

Anywhere between 20 min and 4 hours depending on the load and shipper and receiver.

 

Don't forget your PC hours...with our parking crisis, dropping the load off may be the only safe option you have...

 

If you're close to home and run out of hours, you can log PC to get in the rest of the way...or maybe you can't. Don't mind me, I don't use a logbook.