Longboard shops in the midwest? I know there isn't such a thing in the Chicagoland area. Maybe a skateshop or two that carries loaded, but that is about it for retail shops. Your best bet is to check out online shops like milehighskates.
Phase II over on Farwell and North? (I'm not sure which intersection, it is right next to The Oriental, a movie theater, on Farwell) They carry Flexdex and a few other brands. Not a huge selection but they've got some stuff.
Yeah - the place on State Street in Madison is actually Freedom Skates. But you hafta enter through Knuckleheads to get there. Freedom's in the back of the same retail space.
They carry lots of longboards and wheels and trucks. Landy, Madrid, Randall, Bear, ABEC 11, Hawgs, you name it. Austin and Doughnut are stand-up guys. They'll take care of you. If you want it and they don't have it, they will get it for you. Usually pretty quick too. Unlike most skate shops, the store isn't 20% hardware and 80% clothing. Just the opposite. They have a couple t-shirts and some hats, the rest is all skates.