I had a great weekend in Chicago with my best friend. While it wasn't super-cheap, we made it affordable. We have similar budgets so that always helps. I got the AAA discount on my train ticket, shaving $4 off, got a great rate on the hotel which was withing walking distance of the train station and had a great free wine hour in the afternoon and coffee/ hot chocolate in the morning. We saw "The Santaland Diaries" (for mature audiences from a David Sedaris story) on Friday night and figured out how to take the el to the theatre. Transportation was a bargain all around. The free wine hour saved us $ on cocktails with dinner, and we had great meals. Saturday night we went to the new casual and cheaper Rick Bayless place, Xoco, which was great. I bought nice, interesting, affordable Christmas gifts for DD and DH (including a tie with an understated map of London for DH) and today was the Art Institute which had a fabulous free Beethoven string quartet concert. I'm in an art/food/culture swoon. Very worth it! And CB--that Marilyn statue is huge! She looks very cold there over the river!