Gawd. As if Canadians are too dumb to go to international conferences like everybody else. Maybe they wouldn't let us in because we are wearing toques and speak in funny accents.
Source: I am an American who has visited Chicago 3 times and hated it more and more each time due to prices, crime, horrible weather, and extreme lack of anything to do
It’s the original skyscraper city with an absolutely wonderful skyline and architecture. Being in the city during a blizzard is magical, and the weather on a nice summer day. Tons of parks and pristine coastline. One of the best food and shopping scenes anywhere. World class museums. Also, it’s certainly cheaper than SF/LA/NYC. There is a lifetime of things to experience in Chicago.
Source: someone's who's spent more time in Chicago than someone's who's visited a handful of times.
Of course you'd like it, you're used to the place. The city is called "the windy city" for a reason, and is certainly not known to have weather resembling southern California. If you like it, that's fine, but not everyone likes cold, windy midwestern weather.
For prices, your experiences are simply invalid. The OP was likely talking about prices he'd see as a visitor, the large part of which would include hotel rooms. Do you spend a lot of time in hotels near your home? Of course not. And if the OP is comparing various international cities, then I can see why he'd complain about Chicago: it's a large American city and would likely have extremely high hotel prices, because hotels in America are generally very expensive unless you want to stay in a roach motel. It's much cheaper, as a single traveler, to stay in most of western Europe (except probably Switzerland).
The "Windy City" thing has little to do with our weather; winds are empirically worse in New York and San Francisco. If you have almost no experience with the city, it's easy to project and extrapolate from its nickname.
But you're not allowed to say that "the wind" is why you don't like Chicago.
(Fair warning, I have our city's flag inked on my arm, so I may be a booster).
It is a kickass flag, to be fair.
Well New York isn't exactly famous for great weather either...
It’s like saying you can become a good programmer and have a good company culture by going to conferences.
It ain’t going to happen.
Once you have N years, and see and solve X problems you won’t be experienced.
When you first start, you don't even know what you don't know. All the conferences in the world aren't going to help you if you don't know which problems you need help solving.