Need a really expensive restaurant
I know that is a weird request but I have a friend who won a contest at work and the prize is dinner for 2 at any restaurant in Chicago, drinks included. We want to go somewhere that we could never afford otherwise. Alinea is what jumps to mind but my friend was not sure if it was a "real meal" or more of an experience. I am not thinking of places that serve lunch because you can usually get an affordable meal and at least try it. If money was no object, where would you go? Also, is there perhaps some great dish that I should be thinking of? Let's have fun spending some one else's money!
I'm with BRB. Definitely Alinea.
If you're looking for additional suggestions, we've got other restaurants that approach Alinea in price and are also excellent: Avenues, Everest, Charlie Trotter's, Tru, NoMI, Moto, and Spiaggia. You can have a wonderful experience (and you can spend a lot of money) at any of them.
Still, if someone else is paying - Alinea.
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Before you go - I'd triple check there was no cap on what you can spend - I mean, can you buy the $18,000 bottle of Chateau Lafite-Rothschild at Trotter's?
I don't think I'm out of line by saying ALL of the ultra high end places - from Alinea to Trotter's to Arun's even - will come off as more of an experience than a meal.
Sure, Trotters won't be as "weird" as Alinea, but rest assured you'll get lots of foam, dramatic presentations, synchronized plate setting, etc.
Anyway - while I too would go with Alinea - if you can't get a reservation in a reasonable amount of time - easily my second choice would be Avenues. For a more informal experience, ask to sit at the kitchen bar where you can watch and chat with the chefs.
The only caveat with Avenues is that if you are planning to go in the next couple of weeks, they are closed through the end of the month. (The Lobby restaurant in the Peninsula is being renovated, and is using the Avenues space in the meantime.) Other than that, Avenues would be my second choice, as well. (Although I really like the view at Everest; it's on the 40th Floor of the Midwest Stock Exchange building, so you're looking out the windows on the entire city below.)
Blackbird is incredible and is a "meal." Not as insane price or presentation-wise as Alinea or Trotters, but a wonderful meal and a very strong wine list. Nice work-contest!
But, if you are looking to go over the top... Alinea is it. 2 months waiting list for rezzo.