Okay, my turn I guess. Cleveland.
Local Point Person for City: Deena
Possible hotels in City: Many, ranging from the Ritz-Carlton to Econo-Lodge, from Playhouse Square/city center, to lakeside, to lakefront with beach access, to lodges in parks our out on an island. Rates look like they'll be anywhere from 50 to 160 or more a night (I don't think we want the Ritz).
Pros:
There are amazingly distinct ethnic groups here, with lots of authentic, tasty food choices of the German, Balkan, Italian, Asian, Jewish type, with lots of vegetarian options and, from what I hear, good sushi (I don't eat the stuff). There are also often various ethnic neighborhood festivals going on starting in the spring and going through Oktoberfest.
We could charter a train for a wine tasting; and/or a boat for a tour of the river. We could hold the prom in the hotel, on a yacht, at the botanical gardens. Our zoo does not have a spotted skunk, but does have hairy armadillos and an indoor rain forest. We could take a tour of the cemetary where Garfield was buried, or tour a haunted house. Visit Sephora or tour a chocolate factory. The art museum is amazing and free. The rock hall of fame is here and there's always the possibility of catching a baseball game if anyone wants to see the Indians lose embarrassingly. The theater district has a number of different venues, from rock concerts to experimental theatre to dance. For those who are staying longer, there's the possibility of a trip through Amish country, a day at one of the 3 or 4 amusement parks, or a visit to the drive-through safari park or the tiger habitat. The "world's only indoor amusement park" may be going at that time -- it reminds me of a county fair in a steel building.
For late night fun, there's always The Flats a riverfront area with clubs; microbreweries; Howl at the Moon; The Improv; Flanagan's Wake; Men of Steel, an all-male revue; Circus, a strip club; Power Station, a bar with millions of electronic games karaoke and tiki bars. There are lots of places to play pool, including the bar across the street from my house. There are lots of goth and fetish friendly clubs, including two also across the street from my house, and bowling not too far away.
Cons:
The temperature should be comfortably cool, but it will probably rain at least one of the days. Parking is tight and is never free downtown. Downtown hotels are amazingly expensive. There are lots of funky little shopping districts with unique and strange things and a million malls, but not, imo, a lot of distinctive quality shopping. There's good public transport, including the rapid transit train system, but this is definitely a sprawling place, so travel from one end to the other on public transit takes forever. We'll probably need to do some of the driving ourselves for outlying activities. I don't consider this a destination city. There's lots to do and there's a lot of history, but it doesn't have the cachet of D.C., LA or NOLA. I'm not personally acquainted with the clubs I've mentioned, but I'll be glad to check them out if anyone expresses an interest in any particular venue.