Ahh, crap. Oh, well.
Isn’t it obvious? There’s a New York IN Las Vegas. See both at once! (Swing by Paris while you’re at it.)
I’ve been to almost all the cities mentioned here, and New York is your best bet, followed by Washington (if you are interested in museums or government) and Boston. As a native New Yorker I’ve been to London several times and have never thought it just the same. Perhaps if all big cities are the same to you you would think so.
Las Vegas - let’s just say Las Vegas has a New York hotel but New York doesn’t have a Vegas hotel. Not to mention the wonderful good taste of the Paris hotel with a fake Eiffel Tower growing out of the lobby. Great for gambling, but it is hot and crowded. Plenty of shows if you like Cirque, which I do, but the rest seem to be old Broadway shows and washed up singers and stuff for those who want to back to when chorus girls were daring.
I live near San Francisco, and it is nice and small, but come only if you want to spend some time wine tasting, seeing big trees, and looking at sea lions. Some nice museums, but feeble compared to New York or London. No theater worth mentioning.
Chicago - nice enough, but not much of a destination. My daughter went to the University of Chicago and doesn’t miss the town. My wife is from Philadelphia, but would rather visit New York. Miami - if you are 85, sure. New Orleans is great for food, I lived in Louisiana and we’re going back for Christmas.
Most of these towns have a few really great features, but New York has all of them (except redwoods.) If your friend really wants to gamble, put him on a bus to Atlantic City. Not nearly as much fun as Vegas, true, but he can get it out of his system.
UofC is a 5-block-square island in the middle of a warzone. No wonder she doesn’t 
Dowtown/North side of Chicago is where it’s at.
One of the first things they teach you during U of C orientation is how to get the the North Side without getting killed. She also lived near Evanston for a while.
On the other and half of America lives in the suburbs. If you want to see how America lives Skokie, IL might not be a bad choice.
I live in Las Vegas and voted for NYC also. Las Vegas can be fun, but in a very limited scope. If you would enjoy going on a cruise, then you would most likely love Las Vegas. Its like a big cruise ship with no ocean, in the desert.
If you can visit only one city in the United States, I’d vote for Interior, South Dakota.*
*in the heart of the Badlands, a much better destination than a large city which they probably have where you come from.
Vegas might be a cheaper date. But it’s very schlocky and touristy.
If you want to see America as America, yeah, maybe New York. Or LA. Or Chicago maybe.
Or Orlando? Nah. More expensive than Vegas & supertouristy.
If you want to be somewhere nice, there are probably better choices. Key West, perhaps, or…
Screw it, New York & Vegas may be almost as good as it gets.
New York would be like London only without anything truly unique to see except maybe the Statue of Liberty. They have some goofy aircraft carrier museum that is an abortion of history but would be interesting to tour and you could catch a play but really, London would more interesting from a tourist POV.
Las Vegas would be a great jumping off point to tour the West. You could see places like Bryce Canyon, Zion Canyon, the Grand Canyon etc… If you want to see what wide open space looks like that would be my suggestion. Just looking at the stars in an area of 150 mile visibility would be something to see at night. The space station would look like Venus going by compared to most industrialized places which have 7 to 10 miles of visibility.
I’ve been to NY twice and Vegas three times. I vote NY, and it isn’t close. Vegas is a one trick town (two counting illegal prostitutes, ewww). NY has endless things to do and see. Vegas is interesting to see what a version of hell might be that doesn’t actively torture people. It is an evil, creepy place.
Well, most vacationers are not writing detailed ethnographies. Seriously, the reason I said this is that I was thinking back to a pleasant memory of my last trip to NYC. I remember walking to go catch a play, full of delicious Burmese food (who knew they had Burmese food!) and stopping in a little little boutique where my mom bought me a beautiful scarf.
Wait a minute! I’ve never been to NY with my mom! I had seriously gotten the two mixed up. This is something that would never happen with, say, Lisbon and Rio. It’s not like they are exactly the same- and if you happen to be an Anglophiles or really into New York or a megacity connoisseur, for sure you can find a lot of richness. And both are very fun cities. It’s just that if I handed you a map of the world, put a gun to your head, and said “I want you to circle the two cities, on two different continents, that most closely resemble each other,” New York and London would be a pretty safe bet. New York is the one place in the US that most closely resembles something available in the UK.
It’s not the only unique city. It’s just a pretty unique city. When I imagine San Francisco, I imagine looking out a treeless sun-dazzled sea of pastel Victorians tightly packed and perched on the steep hills that roll out into wild cliffs and the blue ocean. No place else looks like that. The only place I’ve been that feels anything close to San Francisco is maybe Cape Town. Paris is unique, Beijing is unique, Bangkok is unique. But if you have any inclination to feel like “big cities are all kind of the same,” well, New York is the big city they are all kind of the same as.
Of course, it all depends on what you like. New York is a great arts’n’culture city and a great top restaurant city, but I’d argue it’s only a so-so exploring funky neighborhoods and hanging with the local city. San Francisco is a TERRIBLE sightseeing city (seriously, don’t even bother with the “sites”) and a pretty provincial arts city, but has accessible local color and exceptionally good low to mid range eating. DC is an A+ sightseeing city and I think the depth of the African-American heritage is pretty interesting, but otherwise everything else is kind of lame. I dare you to try to hang out with the locals in DC- you can go weeks in this city without meeting a DC native. But in San Francisco it’d be pretty easy to meet people who will, say, invite you to their freegan bike co-op party.
Nothing unique but the Empire State Building, the UN, the Chrysler Building, the Guggenheim Museum, Times Square, Washington Square Park, South Street Seaport, more plays and musicals in one area than you can shake a stick at, Macy’s, the East Village, the West Village - and that’s off the top of my head. The Intrepid came after I left New York, so I don’t even count it as an attraction.
You count more than one thing interesting to see in Paris, I hope.
Wow, loads of food for thought here. Didn’t include more options on the poll initially because I was dead set on NYC, my mate Vegas (mainly because we didn’t know much about anywhere else). As for what he’s into - his preference for Vegas says a lot of what you need to know, likes bars, clubs, gambling, bright lights and shiny objects. However, the more I think about it the more N’awlins sounds like a happy compromise.
The idea started when we were discussing road trips, unfortunately for the foreseeable future boring stuff like work prevents it…a big old cross-country, Atlantic to Pacific trip, down through Route 66. That’s the ideal. Sigh, one day…
What might be a real stupid question, but I’ll ask it anyway - are there any places that, say, we should avoid on account of our… foreign status?
Maybe Alabama?
North Korea. 
I was going to say that I visited Vegas and had plenty to do without ever gambling but then I remembered that two of the things I went there for - bungee jumping and the Star Trek Experience - no longer exist.
Speaking broadly, British accents are often perceived as classy- or intelligent-sounding. Think James Bond or some fictional learned professor. Most people won’t give it a second thought and some will think it’s amusing or cool.In some places there may be the occassional person who thinks you are putting on airs because of the accent, but I can’t imagine it causing trouble. Being a foreign tourist, in and of itself, is not going to create any difficulties. Way out in the sticks, you might get the cold shoulder, but so do Americans who isn’t from around there.
The coast to coast trip may sound compelling, but bear in mind that the middle of the country is pretty flat and boring. The fairly modest cities don’t sound like they would be of much interest to you or your friend and there is precious little to see besides farms and ranches. Route 66, in particular, does not have much of interest between its starting point in the (very much worth seeing) city of Chicago and eastern New Mexico, where the scenery starts. Also, if you really wanted to go Atlantic to Pacific, you’d most likely drive through the Rust Belt to get from New York to Chicago. On that segment, your distaste for grey, depressing cities will get quite a workout.
Much better road tripping can be had in the Southwest, the Blue Ridge, the Rockies, and the entire Pacific coast, to name a few.
Friend is 2/3 right. No horrid crime rate. New York is very safe place. Much more so than, say, Atlanta or Philadelphia.
I love New York, but unless you’re interested in the history, or you’re more into the arts (or major league American sports), I’d say go to Vegas.
Spend your money and have fun.