Which hotel would 'WOW!' locals in Chicago if you told them you were staying there?? Is there one that's considered fantastic and what's so great about it? Maybe the Ritz Carlton/Four Seasons/The Omni perhaps?

Is there also a restaurant in Chicago which is also considered 'The Ultimate Dining Experience'??!

RITZ CARLTON is the BEST!!

Second nomination for the Ritz Carlton. Excellent shopping at Water Tower Place. For steaks, try Gibson's, more casual Houston's.

Four Seasons and Ritz-Carlton are considered the best hotels in Chicago. Top restaurants (with very elusive reservations) are Charlie Trotter's and Tru. Everest, Ambria, Carlos' and Le Francais are also very nice, but have been around longer and may be easier to get into. Look at Chicago magazine to get more ideas. (chicagomag.com)

However, you underestimate us locals if you think that staying in a $400 a night room will impress us. Chicagoans are not like that. Now, if you stopped on your way to dinner to shovel an old lady's car out of a snowdrift while wearing your tuxedo, THAT would impress us!

The Ritz is impressive, but I still love the Drake. Ask for a room with a view of the Lake. Plus, you'll be right on Michigan Ave. The Drake is classy.

Hope you can get to Chicago and have a good time, but as soon as I read your first sentence, Jay, I thought of exactly what patg said before I even read her post. The last time I stayed at any hotel downtown, and I did because I wanted to experience Michigan Ave. at the holiday time as a tourist might- everyone looked at me like I was nuts. metromix.com is a good Chicago web site for information you might want.
patg restaurant suggestions are on target too. Many, many Chicagoans, myself included, would never pay that kind of $$$ for tortured food when there are so many reasonable places with delicious choices everywhere. Just stayed downtown and what impressed me was how the cops, sewage/city workers, firemen etc. all are trying so hard to deal with falling ice from skyscrapers and traffic accident victims. Besides that- they are raising money this week for a 37 year old fireman's family (5 kids & 1 wife)who was killed by a drunk driver on the Dan Ryan/Bishop Ford as he was assisting a victim. That impresses us.

Hey patg and Jeanette, you're my kind of people!

IMHO, life is too short to spend it trying to impress other people. Do your own thing.

Thanks for the info guys!-the 'impressing people' was only for prospective business client purposes.

As for our own family holiday, we're going to a nice small unassuming hotel and just going to soak up the city's atmosphere as tourists! Chicago sounds great -those stories are heartwarming!

Ok, Jay, if we run into you we promise not to be impressed! Seriously, have a great time visiting Chicago. The restaurants I mentioned earlier are not for kids, but try these places for families (assuming kids are older than about 6)
Berghoff's - a Chicago classic
Zinfandel's - upscale but with American favorites on the menu (including a root beer float for dessert!)
Cafe Iberico - authentic Spanish tapas
The Signature Room on 95th for lunch - big-time view and it even has a kids' menu
Heaven on Seven on Rush - Cajun food, very family-friendly

The kids'd would also enjoy Ed Debevic's. Or Pizzaria Uno or Due.