I generally have good experiences redeeming DL miles for both domestic and international flights, also being based in MN. But I don't recommend them to most people. It takes me a LONG time to find award seats using various sources.

My suggestion would be to concentrate on UA miles or programs where you can transfer miles/points to UA, like Ultimate Rewards. Connecting in Chicago is not a big deal if you can find low level award seats vs. flying with DL but paying tens of thousands more miles.