Indianapolis to Eagle River (where we go more often than not). If it's just me in car, it can be done in 8-9 hours. If it involves a trailer, not driving through cook county at the right time, moving sleds around, it can be 11-12 hours. If I leave work at 5, I can get up there in time to hit the trails mid-morning the next day. On the way home, usually ride all day and then drive home. I usually end up getting home in the middle of the night so I take the next day off and hang out with my 3 year old. If I can ride for 4 days, it's all worth it.
Sometimes drive up to the Paradise area instead or MN.
Last year's trip out to Togwotee was just a wee bit longer...