In a few weekends if the weather is good I'll be flying from Chicago (KUGN -- Waukegan) to Middleton-Morey next to Madison.
For you guys in that area, what do the locals typically do? Is Madison Charlie easy to transition through from the east? I've driven through there a few times headed towards Devils Lake, and being right there under the C doesn't bother me as much as that being combined with those few 1400'AGL towers within 3ish miles of the airport.
From the direction you're coming from, you have two options: One is to swing around to the west and avoid the charlie, which I don't recommend. The other is to talk to ATC, and the Madison controllers are very helpful and friendly.
It looks like a direct route will keep you just outside of 5 miles from the Madison airport. Madison lands and departs either north (36, 32, and sometimes 3) or south (18, 21, and sometimes 14). If you listen to their ATIS on 124.65 before you call approach, you'll know which. If they're landing and departing north, you'll probably want to be fairly high when you pass south of the airport (like, say, 4500 MSL). If they're landing and departing south, lower is probably better - maybe 3000, since there may be other planes doing a city tour below that when you pass through. If you want to see the capitol, stadium, etc. on your way to Morey, just ask Approach for a city tour and they'll let you circle downtown for a few spins.
Being from the Chicago area, you're probably fairly used to the TRACON doing their best to ignore you (though they have improved in recent years). Madison is exactly the opposite - Helpful, friendly controllers who I've *never* heard deny flight following or a transition through the Charlie to a single airplane, and I've been based in Madison for most of the time I've been flying.
Enjoy your trip!