After the week’s trips to DC and Chicago, and reasonable exposure (3+ trips) to all of America’s most populous and famous metro areas, here’s how I’d rank America’s big cities in terms of visiting:
World Class American Cities, in rank order
#1 Chicago (3 visits). A car city that also has good public transport. Friendly people all around, tons of obscure international culture and cuisine. Chicago’s immigrant history, the meat packing, all seems to echo the wide gritty boulevards.
#2 DC (lived there). Everything good is free, and the impressive monuments and museums here are pretty amazing. Plenty of international culture. Weather is the huge downer (summer especially) but a lot of intelligent and interesting people to talk to. A great place to live, at least before you get sick of everyone first asking what you do and see if you’re worth networking with.
#3 New York (10-ish visits). Maybe if I cared about fashion or believed like everyone else that it was the world’s best city I could deal more easily with the pretention and numerous strange social elements. Still, I must acknowledge that it’s a unique place. And things are real and broken, the cradle of hip hop and much else that is good about American music.
#4 San Francisco (3 visits). It’s NorCal’s capital and so very different from any other American city. The city’s history is amazing, nature is good, and there is a broad array of attractions. Oh, but it kind of smells, even for a seaside city.
#5 Houston (lived there). Not nearly as bad as its reputation, and it’s our 4rd biggest city after all. Excellent food, good diversity and live music. But yes concrete and humidity ruin it for most people.
#6 City of Fallen Angels, Hell-A (a dozen+ visits). Like All of America’s most famous cities, I actually like LA. Specifically like the gritty Hispanic parts, Santa Monica and a couple cool ethnic neighborhoods. And the weather. And I could almost get over its mortal sins of an overly plastic culture and Hollywood if it weren’t for the traffic.
#7 Maybe Miami would be the best option if we include a 7th world-class city? Can we honestly call anything else world-class? Detroit in 1970 was probably cool. New Orleans in its heyday could also contend. Bostonians think their town merits a world-class designation but I won’t give it out for anything except their autumn leaves and academia. Wedged between DC and NY, I can’t be convinced that Philly adds a whole lot of new anything but some American history for an international visitor. And whatever lists it might be included on, Phoenix rates last.
***Bonus list for fun: Best Non-World Class Cities (i.e. America’s best big towns)
1) Seattle. Really a cool diversity of neighborhoods. Plus unparalleled views of mountains from the city and great access to all kinds of nature. Main downside is the gloomy weather for ¾ of the year. Would be hard to live here.
2) San Diego. Zero pulse for a city of 3 million, so it’s not the most exciting city for an overly cultured urbanite visitor. But to surf, climb, bike, swim and run, the best nature and the best weather in the 48 means I don’t know if there’s a better town to live in. Only a tenth of the vapidness and traffic of its big sister LA.
3) Denver. Lacks the ethnic element of most similar sized cities but weather and mountains forgive that.
4) Indianapolis. Actually a cool, sporty city. Who knew?
5) Everything else. I can’t say there are other top-tier towns, though Portland has some charm and wants to be on this list badly. But I’ll take me a first tier real town like Madison or Bozeman instead of a second tier almost-big city.
The reason I made this list was I spend the last two weeks of break split between my two favorite cities in America, Washington DC and Chicago. Chicago is still my favorite American city, its subtle charm attracts almost everyone I know who’s been. It’s not awe-inspiring in any way—more of a town vibe. But an amazing place. Here are a couple more observations on Chicago:
Many places take only cash. I like to stick it to the credit card man, so I like this, but it does get annoying to carry coins. The big advantage is I can keep track of how much I’m spending.
Know what the Midwest it? Young and restless… No, actually, the Midwest is nice. Even bums are friendly and chatty. That goes a long way in a big city.
Very cool neighborhoods of Wicker Park and Logan Square, where I stayed. Supposedly those parts are hipster but in no way does it approach the absurdity of Portland or New York. It’s more just cool, art-filled. creative spots to hang.
The ethnic component of Chicago is probably unparalleled in America. A Macedonian Church and a Serbian Church were both within a block of where I stayed. Did I mention the Lithuanian museum?
Insane taxi drivers. Did I forget this from my last 2 visits or just not remember?
Good political activism. Some protesting Kurds’s shouts taught me the right way to say Turkish PM Erdogen’s name (er-do-hen) followed by “Killer”
By the way, there are black people. In DC and Chicago both. I forget that all the time living in SD…
So Chitown is the perfect city in every way except two: no mountains and no hills. Those are similar but not identical— hills makes running asphalt really tedious and no mountains means no nature on the weekends. Would be a tough place to transfer my SoCal lifestyle. But a great place to visit.