Chicago - so, so fun. I think I’ve been maybe 7 ties.
DC - incredible, just so beautiful and great if you are a nerd. We love Old Towne, Alexandria, the metro area, all of it!
Charleston & Savannah - classic, timeless, elegant, beautiful.
New Orleans, so fun and you MUST stay at the Monteleone!
Austin - gorgeous gorgeous city. Amazing river walks.
Minneapolis St Paul - love the art gallery & the bar scene.
I really like the Midwest but you have to make an effort to get there. Hell, I even like Milwaukee 
Houston is also fun, as is Shreveport. Oh and Pensacola. We loved it there.