You could argue that NYC is a better vacation city than Chicago because Manhattan is compact and walkable and easily navigable by train for the most part.
It's also an order of magnitude more hectic than Chicago, though, and it's not a better city overall.
Chicago rocks. It's got a lot of different facets, but it's definitely not overall-grim like Birmingham, fwiw.
And if you're here between now and mid-November, that's the time.
Public transportation is OK-ish if you're in what most people would consider the heart of town (east of Western from South Loop to Uptown).
The rest of the city has a ton to offer, but you can burn up a week staying within a mile of the lake, no problem.
I often say you can never wear Chicago out, but it very well may wear you out.
I don't begrudge anyone who finds that cities have gotten old. If it's just not something you can deal with, I get it.
The best big cities, in the US in particular, are what they are and always have been--big messy difficult wonderful beautiful fucked-up diverse places.
Living in a homogenous little town would drive me nuts at this point in my life.
Gramsci, you simply have to visit Calumet Fisheries. It's a must.
This is a fact though you have to drive there and it's not "by" anything other than the bridge that Jake and Elwood jumped in the Blues Brothers.
Best fried shrimp in the universe. This is one of the very best food towns in the world, maybe overall the best in the US.