I usually look at the state laws on concealed carry and helmets to plan my route - I go where I can carry a gun and ride without a helmet.

Since you're from Maryland, you are already screwed on both counts, and anywhere you go will have to be safer - I'd say just take the shortest route. I've been to Chicago several times and never had any serious traffic problems on the interstates.

 

You don't/won't need an easy pass if you avoid the toll road ... Stay south of Chicago and you'll enjoy the ride much better

 

If you come through at a weird time I'd take 294 around Chicago, I did this once mid-day on the RKC and had no complaints. If you drive in a large city on the east coast you can drive in Chicago. Otherwise I'd stay on 80 until your past Chicago then the road you choose back north. I39 is the most logical.

The Lake Express ferry travels from Muskegon to Milwaukee so it's more convenient than the northern ferry and it's much faster. Nice detour might be to stop at the Harley museum in Milwaukee.

 

Take I-80 west. Stay on it .. till you get into Iowa....once in Iowa City take 380 north to Cedar Rapids....take route 20 west to Sioux City...then you can take the slab to South Dakota or Route 20 all the way the southern entrance to the black hills.... Pretty great scenery.
Screw Chicago....

 

I have a Utah Non Resident CCW.

 

if you prefer smaller roads and want a more southern route out or back....Route 50 across Maryland, West Virginia and Ohio could be an option. If I remember right 50 goes almost all the way across USA but I have only taken it through Ohio. From Virginia we are taken I64 to get across the Mississippi then state highways to Sturgis this year as we want to spend a day in St. Louis and KC on the way to meet Friends in Kansas for the right to Sturgis.

 

Better have it locked in a case w/o ammo when in Illinois.

On routes - Chicago isn't a big deal especially for someone used to east coast traffic which is much worse. You could do the I-80 thing to Iowa and up, but it's always under construction and boring as can be. I would (and often do) take I-80/90 to 294 and run that up (or down). It's a piece of cake. Even during high volume times it usually moves along briskly. The Ipass system has really helped traffic flow. And on that, definitely bring your EZpass. Unless you're taking secondary roads, most of your ride from Maryland will be on toll roads.

You might consider stopping in Milwaukee at the Harley museum on your way. It's a good time and Milwaukee is a fun city. Very biker friendly. Thursday nights are bike night at the museum. The turn out is always big (unless it's raining).

Or...

That right there is an awesome ride. Especially the parts east of Ohio. I would probably bail off and head NW after Cinci because it will lose it's luster after that. Up to Colorado anyway. Then it will be great again.

 

In that case, you better check Illinois - last I heard, IL, like your home state, doesn't honor any out of state permit. You can go the full length of Kentucky and hit Missouri without going through IL, but it will add some miles.

Unless you want a scenic route, I'd just go up north to I-70 and across through Indianapolis and up to I-90 and just deal with the gun issue the most legal way I could, in IL.

 

From Boston, last August, I cut across Canada from Buffalo, NY to just north of Detroit. From there, South to Muskegon and took the High Speed Ferry across Lake Superior to Milwaukee. Saved a lot of miles and eliminated both Cleveland AND Chicago. Well worth the fare, plus it was a nice break in a 14 hour day.

Posted a video
https://www.hdforums.com/forum/harle...st-2014-a.html

 

I think he'll have an easier time getting a firearm into Illinois.