1st Long Trip

I always left my TT hooked up when stopping for the night or even two. Same thing now towing the toad with the MH.
I pull out the trailer plug and make sure you put a flag on your forehead to hook it back up in the morning.

If you are calling ahead to make sure a CG along your route has sites open......Just ask for a "pull thru" site. Know the overall length of your tow vehicle and trailer and add a few inches for safe keeping. Some CG's will ask for your length so they hold the appropriate length pull thru site open for you if they have different sizes.

And be strong. Some CG owners will ask you if you can unhook. Tell them no and miraculously they will give you the pull thru site. Lately I have found some of them trying to keep them open for the big coaches. IMHO that's too bad. I'm here they are not, I am not unhooking and I'd like the pull thru please!

Have a safe trip! I'm from the WI/IL border and IMHO the weather this time of year there is like no other spot in the US!

Where pray tell are you going to stay at a CG in the Chicago area?

It the site allows it I will leave my fiver hooked up overnight but will take a little of the weight off of the truck with the landing gear (same as the tongue jack on your trailer).

I do unplug the trailer cord from the truck after I have shore power hooked up. I don't think it can hurt anything, but I don't like taking odd chances. Strange things sometimes happen.

Ditto. When we leave the truck & TT hooked up overnight, we usually put down the tongue jack and stabilizers, just to keep the TT from bouncing quite so much when we're walking around inside it. We do leave the Equalizer bars on.

1st, no problem leaving it hooked up. The only possible problem might be in the size of the campsite on your first stop. If room allows, leave it hooked up. It hurts nothing leaving the bars on as well.
As for driving long distances, drive what YOU are comfortable with.