Chicago is my favorite city 12 months of the year. Chicago gets so much bad hype over it's winter but it really isn't that bad. By the way, chicago doesn't even make the top 15 of windiest cities in the US. But it is Number 1 in beauty, style, sophistication, culture, and activities.

Ok, it seems that everyone thinks "their" city is the best. For the cities that I have lived in or visited I'm ranking the urban areas, not the suburbs, or surroundings...(I've never been to the Pac. NW, San Diego, or Deep South.

LARGE CITIES
.NYC
.San Fran
.Boston
.Chicago

MEDIUM CITIES
.Baltimore
.Pittsburgh
.Cincinnati
.Portland

AVOID:
.Indianapolis
.Buffalo
.Albany,NY
.Atlanta
.LA
.Houston

Got to respond to Gordon. I lived across Sheridan Road from Lake Michigan for 22 years in Evanston, just north of Chicago. I thought I'd died and gone to heaven the first Christmas we shopped for trees in shorts in L.A.! It's a beautiful city, Chicago, but maybe it's better for the tourists in the downtown hotels than for those who had to man the snow blowers on the North Shore!! You can love it 12 months of the year, but you've got to love the cold, snowy winters, and also, Chicago did not get the nickname "the windy city" because of the wind--I forget the real reason, it had something to do with a politician!

Great subject--so I'll add my two-cents worth:
I haven't been to a city I didn't like, and, if I were to move from Pittsburgh, I'd probably pick DC...unless you are poor and homeless, DC can be a really fun town. There is something to do for everyone nearly every day and night of the week, and it is so close to lots of other great cities, and the beaches of Deleware, Maryland, and Virginia. I think that the DC Metro (subway) is what I like best about DC...you can zip from one place to the next in a clean, modern, and quite elegant underground train system.

San Francisco is really fantastic as well--it is the place I'd pick if I were penniless and homeless. The weather there is nearly perfect, unless you really like it hot and dry. And, the folks in SF take food very seriously--how could you not like that?

Despite what you might have been told, and heard, Pittsburgh is a great city. It's small, but houses are truly cheap, and there are all the amenities of much larger cities. There are great parks, museums, symphony, ballet, and food, and $20 goes a long way.

As a Canadian I love visiting anywhere in the U.S. but preferably when the $ exchange rate is better. My choices are 1. Las Vegas, 2. San Antonio, 3.San Francisco.

This is tough because there are a lot of great cities. Have to say San Francisco is number 1 and my other choices aren't ranked: Seattle, NYC, Philadelphia, Denver, Santa Fe , St. Louis and Tucson

Haven't been to San Francisco since third grade (about 20 years ago), so I can't vote on that. But have been all over the east coast, Canada, and Europe. My favorite... NYC, without a doubt. Paris, Prague, London, and others come second, but they are not in N. AMerica. I also love Toronto and Montreal. AFter NYC, Washington, DC just doesn't cut it. Nice monuments, museums, etc, but DEAD. Couldn't even find a deli to buy a drink.