AND I think KC is bulidng a new light rail system from downtown/the zoo to the airport...not sure when it will be complete, but that would open up tons of options in the Plaza/city market district for easy commuting...their employee lot, the airport, and the city in general is pretty laid-back and stress-free...just keep in mind the airport is way the heck up the road from the city itself....
If you have a kid, go for Liberty...there are some good subdivisions and schools up there and it's a quick drive to the employee lot. I have a few family members to do the Vegas and MDW commute from KC for SWA, and they seem to get hosed only once or twice a year....I honestly think Denver is a better bet than Chi if you have a choice from my own jumpseating experiences on leisure travel...
I just got my dad a ZED ticket from Denver to MCI, and he had no problems with plenty of seats available on the early morning SWA flights and the afternoon Frontier/United flights....
Not sure what their typical sched is but it looked like SWA had 3 or 4 non-stops, Frontier had 3 or 4, and UAL had several--a mainline 75, an E170, a couple RJ flights also...it looked very, very easy...