Chicago is a pretty good one, as long as you’re not talking about winter. Some good museums and downtown is nice to walk around. Depends on how long though, you might get bored after a few days. If you go to a baseball game, be sure to see the White Sox and not the Cubs.

I’ll plug San Francisco. Ignore what the chuds say about it. You can go any time of the year. And sure, it’s lib city but none of that should matter if you’re talking about just taking a trip. It’s the most beautiful big city in the US, bar none. Better Chinatown than Chicago. Great for walking around because they have good public transit. Marin County (other side of the Golden Gate Bridge) is achingly beautiful, as is the drive down the coast. And if ALL expenses are paid then Napa is great even if you don’t like wine, they have some of the best food anywhere in the country there.

Do not in any circumstances spend more than 24 hours in Las Vegas.