I'm leaving NYC to drive to Kansas City as my destination. I would like to stop in Chicago for a few day, and make it an interesting road trip. I can have my GPS just get me there quickly, but I would rather find sites or towns to stop at. Can anyone give me advice? I would rather not stop in Cleveland or Columbus as thats where I usually stop for the night depending on if I take 70 or 80. I don't mind driving the Penn toll highway, because I've never stopped at Falling Waters or the Fl. 93 Memorial. Thanks in advance for any help. Mary

'Brown County Indiana for covered bridges.

Head for Somerset PA on the PA Turnpike. See both the Flight 93 Memorial and Falling Water the next day. Are you driving back to New York after you visit Kansas City?
If you are renting a car, you might want to take a train to Pittsburgh or Harrisburg and go from there

For myself, I'd skip Chicago entirely and take a slightly more southerly route unless you've never been there before, and then obviously Oak Park is your destination for Wright stuff. The Pittsburgh area is definitely a must-do if you like Frank Lloyd Wright. Falling Water is not the only house in the area (there are three, and you can even sleep in a Wright house nearby if you want). If you travel that way, it's not a huge detour to go through Shanksville for the Flight 93 Memorial, which is near the town, but it's between Harrisburg and Pittsburgh.

I'm not sure I'd skip Columbus, OH this time because of the new National Veterans Memorial and Museum, part of the city's redesigned waterfront. And if you like flea markets there's a huge one between Columbus and Dayton on I-70.

I would certainly recommend a stop in the other Columbus (Indiana), a hotbed of mid-century architecture, and conveniently adjacent to Brown County. If you like whisky, then a side-trip to the Louisville area might be in order, where you'll find numerous distilleries.

And the new plaza around the Gateway Arch in St. Louis reopened last summer; it really does improve the experience, and St. Louis is sort of happening again. There's some interesting stuff downtown as well as remaining pockets of blight. Regardless, it's worth a stop for at least a day (be aware that you can't always get tickets to the arch immediately, so if you go, try to book those in advance as soon as you know which day you''ll be there). Unfortunately, there's not much of real interest in Missouri between St. Louis and Kansas City.

Thanks everyone for your advice! We'll do the PA turnpike, and stop in Somerset for the night. Then onto Chicago and St. Louis. Maybe we'll happen on somewhere cool!