My mom and I like to go on a long weekend trip together every year. In 2016, we need to do a driving trip to save money because H and I are taking a 10-year anniversary trip. We have been to most of the places within close driving dostance from Chicago...Madison, Milwaukee, Galena, St. Louis and Nashville. Would KC be a good choice? We would likely bring Jack (age 1 then) because I have a bunch of work trips and the anniversary trip already.
What are some fun things to do? And KC ladies, my mom would happily babysit one night if I can convince you to meet me for dinner/drinks/something!
I think Kansas City is a great option! Union Station, WW1 Museum, several different art museums, the Plaza is great for high end shopping or walking around to enjoy the architecture, our downtown area has seen a great revitalization in recent years and has fun places to eat. Just south of downtown there is the Crossroads area which is a booming arts, galleries and restaurants spot. Tons to do and see!
With a car, there's definitely fun stuff to do in KC. My kiddo loves the zoo, the Nelson Atkins Museum is awesome, the Union Station model train exhibit is very cool and has a play area for small children your kid would love, and tons of great restaurant options.
Kansas City has a lot of family friendly things to do. And pugz knows about pretty much all of them, ha! We can definitely do a get together if you like. It seems like there are a lot of new attractions that have opened in the last few years.
Milwaukee and Cincinnati are both much nicer drives than Kansas City. Plenty of kid friendly things there too for a short stay.