If you have extra money to throw out the window, I'd say go for it :)
Don't go on a rainy day or cloudy cuz then you can't see everything you want to see. You want to be able to see the city soldier Field in the Wisconsin all that on a cloudy day you're not going to see
So yes and no, if there's clouds it will be really cool to be level with them, you obv won't see as far out which is crazy cool. I'd still do it tho
The place is usually crowded rain or shine. So I would advise doing it on a sunny day (atleast your pictures will be better)
I dont think so, in my opinion depends to the crowding
Yeah... It would be waste of money to visit on a rainy day. Plan for a clar day. You can enjoy the beauty of Chicago
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