Greetings to all you afficiandos,
I would greatly appreciate your help. I am staying in Chicago for 5 days while attending a conference. I will be meeting someone for the first-time as well. We share similar interests and I am expecting nothing less than an enjoyable rendezvous. Since is this is the first time we will both be visiting the windy city may I have some quixotic suggestions?
Also, I have surveyed all the listings of hotels and NO ONE has mentioned the Knickerbocker...am I making a mistake staying there? I am interested in various topics, love walking, and am a native of NYC so a city's allure to me is multidimensional.
Thanks for your suggestions and help

Appetizers and drinks on the 95th (96th?) floor of the Hancock building is nice.

R: You don't mention when you are coming; please provide info on that - may impact outdoor activities.

I think the Knickerbocker underwent a renovation a few years ago. And isn't it part of a pretty reputable chain (name escapes me at the moment). The location is excellent - directly across from the Drake and steps from N. Michigan Ave. I think you'll be fine.
Hope your romance expectations pan out...!

For a truly romantic and unique dining experience, I would like to suggest Geja's Cafe at Armitage and Clark for a fondue dinner. You won't regret it!

I agree with the suggestion for drinks and appetizers at the top of the Hancock. Dinner would be ok there to but $$$$$$

Chicago Magazine has a free service where the dining editors of the magazine will plan a restaurant date for you, you just have to supply price range and preferences.

http://www.chicagomag.com/planadate/index.html

Thank you all. S: I'll be there over Halloween into the first week of Nov. May I ask also; How complicated is the train system? I have several maps and have managed the likes of the Metro, Marta and Europe well, but I know how crazy the Manhattan system is. Do I need to worry?
Any ideas for a day trip?...

The subway/el transit system is quite siimple to negotiate. Maps are on a par with NYC or London, so you should have no trouble getting around. As for a day trip, if it's your first visit and much of your time will be spent on business, I can't imagine anything better than just strolling and getting the flavor of the city. Take in the Art Institute, then walk north on Michigan Avenue to its terminus at Oak Street - a couple of miles that will take you the stretch of fabled North Michigan Avenue (and right back to your hotel). Or (and this all assumes good weather of course), walk north from your hotel, down Lake Shore Dr. to Lincoln Park (about 1 1/2 miles) and on to the zoo - another half mile. You can cut in from Lake Shore Dr. to Astor or State Parkway for a stroll thru the Gold Coast neighborhood - stately old homes, quiet streets - very posh and pleasant.