Maybe this isn't what you're looking for, but I'm going to suggest it anyway. You should really go to House on the Rock. It's in Wisconsin, and it's about a four hour drive from Chicago. Not exactly a long road trip, but you could do it on your last day before work or something. I remember enjoying the scenery on the way to and from, for what it is. Lots of pretty farmland and wide open plains, and small antiquated towns that look like they came straight from the 1800s.
But anyway, House on the Rock itself is basically just some rich dude who is now dead decided to build the biggest collection of weird shit ever. There are tons of incredibly large collections; doll houses, suits of armor, old toys, instruments, newspapers from world war 2, etc. So it's half museum, I guess, and the enormity of the collections and the way they're presented put the actual museums in Chicago to shame. I went to the field museum for the first time since I was little a year after going to House on the Rock, and it was the biggest disappointment ever.
The other half is stuff he had constructed by an army of workers and artists. A sculpture of a whale and a fisherman in a paddling boat both cresting a huge wave that takes up an entire two story room. The world's largest carousel. This thing called the infinity room which juts out the side of a cliff over tall trees and gets narrower as you walk down it so that it looks like it goes on forever. A small recreation of a Victorian-era street indoors. There are multiple Japanese gardens and they are all gorgeous. It's all stitched together in a haphazard fashion which, combined with the sheer enormity of it, makes you feel like you're walking through some crazy fever dream.
One of the coolest places I've ever been. I can see myself going back there every few years for the rest of my life.
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