Flying in for Oprah show, spa, shopping, sightseeing and the best food and nightlife we can fit in for 3 days in May to celebrate the big 4-0. Sky's the limit!

If you could treat yourself without limits, where would you go/stay/play?

Oprah's place on Maui...

http://www.architecture.org/tour_view.aspx?TourID=8

Architecture Boat Tour

Show? Wicked
http://www.wickedthemusical.com/chicago/

If you are a real Wicked fan, click on "Behind the Emerald Curtain" for tour info

As a Chicago resident, I can't help with where to stay specifically (though you will likely want to stay someone near North Michigan Aven).

The best places to dine will be subjectvie depending on what type of food you like. My personal favorite in the "money is no object category" is Japonais (sushi). It's not near much else (not really out of the way, but not in the center of everything).

I think to get very helpful responses, you may have to provide a bit more about what you like to do.

For me...I am not money would make much difference for a lot of things. My favorite things to do in Chicago are free - walking down the lakefront or through the neighborhoods.

Sounds like a great celebration! We stayed at the Fitzpatrick (Fitzgerald?) -- it was moderate but nice and half a block from the the great shops. Had a really nice Mexican dinner at Adobe and then went next door to Second City. A fun evening.

Cafe Spiaggia right on Michigan Ave. is lovely for dinner. Quiet with beautiful decor, good service and good food.

You can google to find it or make ressies for it (and many other restaurants) at www.opentable.com which is quite convenient.

Cafe Spiaggia is the less expensive sister to Spiaggia just across the hall and they share a kitchen.

I guess if the sky is the limit I'd do Spiaggia instead of Cafe Spiaggia.

Here is info from the opentable website. "As Chicago’s only four-star Italian restaurant as rated by the Chicago Tribune and Chicago Magazine, Spiaggia offers an unparalleled fine dining experience.

Chef/Partner Tony Mantuano, James Beard 2005 Best Chef Midwest and his team deliver world-class Italian cuisine . Nominated for Outstanding Service in the U.S. by the James Beard Foundation in 2005 and awarded by Zagat as "Chicago's Top Italian Restaurant,"

Spiaggia offers an inventive wine selection and a spectacular view from a dramatic dining room."

Probably the most adventurous place for food is Charlie Trotter's, but it has to be your kind place. There are 7 or so courses of a few bites, but each dish is very creative (not strange) with multiple sub-recipes, i.e. NOTHING you will ever do at home, or find at many restaurants. There are only two menus to choose from - vegetarian and dishes with meat and veg -- but they are very accomodating about switching courses between the two. You basically turn yourself over to Charlie for the evening. Cost: $150 pp without wine. This is in the near-North area, i.e. a relativley short cab ride into a fun neighborhood.

If you wanted to stay more in Magnificanet Mile area, Tru, the dining rooms at the Four Seasons, Ritz, and the Peninsula hotels revive the idea of fine hotel dining. While not to-the limit, Arun's for upscale Thai is wonderful; Spiaggi fin e fine northern Italian cuisine with dramatic views and room; and Alinea is fab for "new American." Find a copy of Chicago magazine for others you might enjoy, with relaible reviews.

For shopping: you wil find all the usual suspects, i.e. good rpepresentations of Neiman's, Saks,s and Barneys, but Ikram on Oak Street sets the standard for point-of-view high-end clothing.

Chicago has first-rate culture in its ARt Institute of Chicago, theater scene, blues clubs, and opera. Whatevber your pleasure, on a quieter scale than New York but no less pleasing.

We had a wonderful 'tasting' dinner at Tru. To be honest, though, while those dinners are fabulously interesting, one or two in a lifetime is about all you need.

Thanks for the great suggesions...I'd like to hang at Oprah's Maui pad too

How about hotels? Peninsula or another?

If you'll be there on a Sunday, brunch at the Drake Hotel. Any other day, breakfast at Orange in Lincoln Park. Eau. Muh. Gawd.

I hope this reply isn't too late. Sky's the limit hotels include the Peninsula and Park Hyatt, both just off North Michigan Avenue. Park Hyatt has a Tiffani Kim Spa there. Service at both hotels is excellent; Park Hyatt is more contemporary.

Love both the Park Hyatt and the Peninsula...you can't go wrong. Four Seasons is under construction so I wouldn't do that. I LOVE Spiaggia!!! SO good. We go every year the day after Valentine's day. I agree about Tru and Charlie Trotter...while interesting...only a once or twice every decade thing. You should try to see Wicked. Atwood Cafe or Trattoria #10 are great places nearby for dining. If you stay at one of the above hotels the concierge should be able to get you in to any restaurants you are interested in (don't call yourself...have the concierge set it up even if you call him/her before you go...they get tables you and I don't!) Have Fun!

PS: for a less high end hotel we LOVE the Talbott Hotel's corner King Room and their One-Bedroom Suite. Prices are almost less than a small room at the above hotels. It is really nice and right down the street from the Four Seasons. It has a great Bar and restaurant in the hotel (Bice Cafe).

Thank you. Everyone has been so helpful and I am incredibly excited (and impressed) with all of the amazing hotel choices! After looking at many options, I am starting to think that having a river view might be quite nice.

What would be the most romantic, scenic and cool room/hotel that is still convenient to great food and museums?

A Chicago River view IS the best choice- nice. And it is my favorite location because it is between the Loop and the N. Michigan Ave. Water Tower corridor areas. Quite handy. Omni or Renaissance, I think has a river walk. Swissotel you are not in the same category but it is 4 star and has the best view of the entire lakefront from its gym on top. Walk up there if you are on the river and have a chance.

Hmm. I checked out the Omni but they do not have any water views. Swiss is sold out. ANy others that would be good?

Birthday trips are the best,fellow May baby.

Hi
I just got back from a Oprah trip yesterday and because of the reccomendations here ate at Cafe Sapggia. Delicious!!! Best gnocchi I have ever had. The other resturant to uptight for me and when the waiter told us same food better prices and the atmosphere was fun. Loved it!! Have a good time.

Hey Momof5- Glad you enjoyed Cafe Spiaggia. Good to know about the gnocchi. I had the best crab cakes ever (from the appetizer menu)the first time I went.