Now i am wondering if i should go up that way or through Wisconsin???

 

Stay away from the Chicago area ... Way away

 

Jus' sayin' IF you have enough time you may want to consider doing the far west side of "the mitten" following the Lake Michigan shoreline.
RT 31 to RT 119 then over to Mackinaw City and the "Mighty Mac" .for scenery.

RT's 131. 127 and 23 are all longer routes (west of I-75) that run somewhat paralell (north/south) to I-75 with I-75 usually being the shortest and the fastest route to the "Soo".
Regardless of the route you choose I would highly recommend that you avoid doing the drive on a Friday and especially at anytime after noon as the northbound traffic can be very heavy, especially on I-75 and RT 23.

There's a lot of construction almost everywhere in Michigan in the summer months so be prepared.
IF....you decide to take I-75 through Detroit, I'd recommend a morning ride (after 10AM or so) but even then the traffic in Detroit is much lighter than most think just avoid the high traffic times and late at night.

I'm sure you're aware of what documents that you will need to cross the border into Canada and their restrictions.

 

I don't like anything about down state, so I would do WI
When going down south I do either 55 or 57 through IL. Go west Beliot Rockford. On paper is is little longer, but is is easy miles and guaranteed time. I did Chicago years ago, because I need to. Right time of day, usually helps.

Million different routes through UP and everyone has one they like.