re: Road trip to Wisconsin for game. Need help

How long time wise are you making your trip? If you have time go up one way and come down anothr, long boring drive second time around. Seeing something different will help it stay moderately refreshing.

Get yourself Roadside America app for your phone. You can find all the crazy things along your route and project your rooute to plan. Things like the worlds largest ball of string etc. you can check it out first on roadsideamerica.com

Beale Street, St. Louis Arch and Chicago are all musts if you have not seen or been there before.

In Wisconsin if you have time:
Madison - City and Campus - Camp Randall has a Confederate graveyard from the civil war if you are a civil war buff.

Wisconsin Dells - Water park capitol of the world. Giant tourist trap but fun.

House on the Rock - Home turned museum that is pretty cool.

Devils Lake State Park - Between WI Dells and Madison. Nice stop if only for a couple of hours.

Cave of the Mounds

Cubs and or Brewers Games.

Histotic Route 66 I have never taken this portion so not sure what that will be like.

If you have time it is a nice drive along the Mississippi River. From state to state. The western lower half of the Mississippi in WI is a great drive. But that is a time thing and on the other side of the state.