Recently visited Chicago for the first time, and have been back once or twice since. I really liked the vibe there. It felt like it had a lot of energy (similar to New York) but felt much less claustrophobic, a bit more open, and a bit friendlier? I don't know if that is Chicago's reputation, but I really liked it there. Great freakin food too. Monteverde, so good.
That's pretty much exactly Chicago's rep; it's the US city most like New York City, and it's of course not really like it at all, and some of the many ways it's different (alleys and garbage collection, seeing the sky) are improvements.
That's how I feel, too. And I do think that the city has a midwestern friendliness (especially in the neighborhoods, outside of the loop). I haven't been to Monteverde, but I'll check it out!
Pros:
- Beautiful lakefront, architecture, & parks
- Dense, walkable, & easy to get around by train or bike
- Tons of cool things to do & people to meet (festivals, concerts, meetups, clubs, museums)
- Relatively inexpensive, especially compared to NYC or LA
- Within driving distance of my midwestern family
Cons:
- Car traffic is often bad (I don't drive in the city)
- I often have to switch CTA train cars because of people smoking on the train
- Winters are cold (I'm used to bundling up)
- Property tax rate is relatively high