S,
No Chicago coming down I-39, to Bloomington, then I-74 to Indy, then I-65 south...

I tow my 10' 3" cat everywhere with a dually. I agree a dually does make the boat look less wide. I also live in the Chicago suburbs and have had a wide boat for the last 20 years with no issues traveling on highways and side roads in Illinois. A 9' 6" cat should be no problem. A big wide cruiser on a trailer looks massive compared to sleek offshore boat.

Well you will get to find out how nice our roads are, last trip i took some off ramps were like we were offroad.

I have towed my 308 to NC multiple times as well as the FL Keys which seem to be even tougher on width with never an issue.
I would think under 10' you will be fine with no issues

Here's the Mule that's going to pull it home...
https://cimg5.ibsrv.net/gimg/www.off...2002f1964c.jpg

I pulled my 3212(10-6) all over N America with no problem and no permits.

F350 Dually
F650
F250 SRW

The SRW definitely showed the boat size far more than the others but still rolled along.

I’ll wave at ya as you”re passing by my house once you start heading East on 74. :flag:You shouldn’t have any issues on that route.

Wave to me as well when you pass the Corvette museum and race track in Bowling Green KY. No one ever has problems in Kentucky or Tennessee.

I have pulled a 46 Skater for 5 yrs on a flat trailer with no permits but I did put oversize load signs and flags on the back corners. I have also pulled a 41 Cig CC from MI to FL for 5 yrs with no signs or permits. it is 11ft wide I wouldn't put any signs or flags on a 32, it will just draw attention to you. Do not go into any weight stations or check points like the one at the FL line. You are pulling it illegally and that could change everything if you were to have a bad accident, Sorry didn't mean to ruin your trip. It will be fine, Congrats on your new boat. My bother is redoing a 32 right now, really nice boats.

I just seen that ad the other day, really nice boat