Originally Posted by
Big Mo
I can't answer the East/West question. IMO, some of the western cities you listed are not even similar to each other, and Chicago is similar to none of them. Chicago is less dense than NYC, but retains a strong urban core and has a huge variety of neighborhoods that a young couple would enjoy, all accessible by public transportation. The natives have a reputation for being very friendly. The beaches are excellent in the summer, and there are tons of street festivals. Chicago is on the short list of top restaurant cities in the U.S. and arguably is #1. The bar and club scene is very highly regarded nationally, and so is the art scene.
Click around this forum for specific recommendations or, if you want something more tailored to your interests, let us know what they are. I'm sure you'll have a great time.
I'd agree with all of this, though I don't know anyone in their right mind who would say that Chicago is the best dining city in the country. That accolade clearly goes to New York City...though I'd say Chicago is a respectable second.
I usually describe Chicago as having 90% of what New York offers in a much more livable and affordable city.
For example, in New York you can get anything, any time. In Chicago you can get almost anything almost any time.