Shoot for
La Crosse, WI. One or more of us could meet you there to escort you toward MKE.
Welch Motel is on the south side of town, on the Mississippi River, WI 35. It's a real real nice Mom and Pop. d j, Tonya and I stayed there the night she passed through that area on her Grand Adventure.
From there we could take you to the
Mindoro Cut and tool around SW Wisconnie road goodness to get you to MKE. We could kill a day just playing around between LSE and MKE, easy 250 mile day ride. Find some fresh cheese curds along the way. Visit New Glarus. Plenty to see out that way.
I live 45-ish miles due south of MKE and could probably put you up for a night or two. Visit the H-D Museum on the second day, have lunch at the
Safe House downtown MKE, whatever you wanna do. Three H-D dealers within 25 miles of my house in case your bike needs some attention, plus three in greater MKE in case stuff arises sooner.
Summerfest is on MKE's lakefront the beginning of July for like 10 days and is a good time if you like food, beer and tons of live music.
Depending on your plans, you could bypass Chicagoland's hellish x-ways by taking the
Lake Express across Lake Michigan from MKE to Muskegon, MI and head to points east and/or south from there. I rode the Lake Express across Lake Michigan a couple of summers ago, Muskegon to MKE, last boat out. It was a nice ride.
Food for thought.