Hey Anthem,
I'm assuming you are flying into Mitchell. Downtown will be 10 minutes from the airport. There are several cigars bars to hit, as well as some very nice pubs/restaurants that are cigar friendly. Uhle's is downtown (never been) and there is a great Irish bar a block from there that is cigar friendly. Jack's is a place I visit when in the area, but it is around 30 minutes northwest of downtown (40 from the airport). Nice ash in Waukesha is a nice cigar friendly bar about 30 minutes west of down town. If you head out to Delavan, you are looking closer to an hour west from downtown Milwaukee I believe. Just an FYI.
I'd be up for heading downtown to Uhle's and Mo's Irish Pub. I could probably do Jack's or Nice Ash as well. If you want a cigar shop closer to RyJ there is Prime Cigar in Brookfield. They are a cigar shop with a full service bar. Some nice places to eat nearby as well.
I've got a second kiddo due in March, so I will need to observe hormone levels next week before fully commiting. Hope to me you guys out!!