27. Detroit: Never a good sign when you insist on staying at a hotel at the airport.
26. Indianapolis: Always seems to be minus-147 degrees.
25. Houston: Kind of boring, unless you enjoy Whataburger franchises on every corner.
24. Salt Lake City: Nice skiing, I guess.
23. Sacramento: The worst arena in the NBA definitely doesn't help matters.
22. Milwaukee: I went to school in Wisconsin and have several friends in Milwaukee, or else it might be giving Detroit a run for its money on my list.
21. Orlando: Great for families but not so much for single, thirtysomething sportswriters.
20. Memphis: Beale Street is fun for one night, but what if you have to stay two nights?
19. Cleveland: The Rock and Roll Hall of Fame helps, as does the underrated downtown area.
18. Atlanta: You've got to give credit to one of only three U.S. cities to host a Summer Olympics.
17. Charlotte: It might be a little too high on this list, but I've never had a bad time there.
16. Dallas: I hate the Dallas Cowboys. Hate, hate, hate.
15. Philadelphia: Cheesesteak sandwiches at Pat's or Geno's? I never decide until I get there.
14. Toronto: Canada's answer to New York City.
13. San Antonio: The River Walk is fun, and Austin is only an hour away.
12. Boston: Whenever I leave, I feel like I could use another day to see everything I missed.
11. Denver: Downtown is surprisingly vibrant, even when there's a foot of snow on the ground.
10. Portland: See Seattle.
9. Minneapolis: Seriously underrated. I'm being totally serious.
8. Phoenix: Just don't go in June, July or August.
7. New Orleans: Bourbon Street is on the rebound, as is downtown.
6. Washington, D.C.: My favorite daytime city in the U.S. Where else can you see so many memorials and monuments?
5. San Francisco: The Golden State Warriors are in Oakland, but those in the know stay in S.F.
4. Seattle: Clean, crisp air makes it a must-smell.
3. Miami: South Beach is simply phenomenal for so many reasons, day and night.
2. New York/New Jersey: Always something to do. Always.
1. Chicago: Like New York, but without the attitude.
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