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?