If I go visit my parents they are north of Milwaukee an hour so any flight home means a 2.5 hour drive from Chicago. Its a pain but I can usually convince my mother to stop at the excellent pizza place in downtown Milwaukee on the way.
WOW and Icelandair just started a bunch of new services, including one to Kansas City. I don't imagine anyone is going to start Milwaukee anytime soon!
If you know where to look (google flights) /work the fare classes it can be pretty easy to get decent fares (some amazing deals out there right now in economy) or even premium+/business class fares for fairly reasonable prices and not much of a premium over economy. A few tricks involved backing out into a start point in Europe (Dublin, Stockholm, Oslo, Sofia tend to be excellent starting points) and checking from there. We also run a lot of money through a BA credit card and play the Avios game - best used for upgrades or shorthaul into Europe. All this tends to work best if you have flexibility or can fly on shoulder seasons like late Spring or early Fall.
I do like Norwegian and have taken them plenty of times shorthaul to Sweden and would probably consider them longhaul to the US. However, even considering traveling light with a wheely suitcase and going somewhere on the east coast for a few days (buy cheap electronics,see a museum, etc), it still isn't going to compare to what I can get on BA for a flight that short.