@mullinscmu: Hello! I LOVE Chicago… I went to graduate school there and would just love to get back up there one day. Luckily my fiance is from there, so we get to visit just about every year to visit family.
ANYWAY, back to your question.
1. I would completely rule out Historic Rice Mills. It is REALLY tight on space. We were only planning for 100, and we could not imagine getting that many people crammed in there. And the outside space, where most people do the ceremony, is even tighter. Also, it’s on the other side of the pennisula, which isn’t really close to any of the cool downtown area, so all your guests would have to be shuttled around (or drive themselves), to your venue, versus picking a venue that is close to all the “action” on the east side of the pennisula. If you have a lot of out of town guests, I would definitely encourage you to find a place that everyone can walk to, or get a quick cab/pedi-cab ride to.
2. We visited the Confederate House (Confederate Home and College). It has a great space. Susan Sarandon’s daughter actually was just married there last year! =) Anyway, the outside is really beautiful and could totally accomodate your guests, but the inside rooms might be a bit tight if you have dinner there… But it’s been a while since I was there, so I could be mistaken on that. The best part is that it is very inexpensive to book, maybe $300-600, and the money goes to maintaining the property and helping the women that live there.
3. I am getting married at the Old Exchange and it is AMAZING. You can’t really get more Charleston or historic. It’s one of the top three important buidlings in our country. George Washington has dined in the top room and the Declaration of Independence was read from the front steps way back when. Anyway, 140, might be a little tight, but they say they can accomodate 150 for a seated dinner.. The top floor room is just oozing with class, you really wouldn’t have to worry too much about decorating it… It has two huge fireplaces and tall majestic windows on two sides. All we’re really adding are tons of candles and a few flowers! It’s a bit pricey to rent ~ $2500, but totally worth it in my opinion.
4. I have not been to the Lagare Waring House or Wickliffe House, so I cannot comment on them… though I know Lagare Waring House is out of this world. My fiance is a professional photographer and he is always blown away by the weddings that he’s shot there! I think it’s pretty pricey, but no doubt totally worth it..
Anyway, sorry for my book… Let me know if you have more specific questions. We LOVE Charleston – you will have a beautiful wedding regardless of what you choose. =)