Fiance and I are taking a weekend trip to Chicago since neither of us have ever been. What's the one date night restaurant that we have to go to? This wouldn't be for a couple months, so if it's a place that needs reservations way ahead of time, we may still have time.
Alinea is ridiculously hard to get into. One of the best restaurants in the world. A real foodie place, but if you want an interesting high end experience, many foodie people I trust say its one of the best restaurant experiences they've ever had. Reservations needed far in advance. Girl & the Goat is a fantastic place too. I agree with both of those recommendations.
If you want a little more casual and are feelilng Italian, I like Rosebud on Rush. Great italian. Sausage and peppers are insane. Couple of blocks from MIchigan Avenue, around the corner from the Peninsula Hotel.
If you want a steak and some stone crab claws, Joe's Seafood, Prime Steak & Stone Crab. I love Joe's. Probably my favorite restaurant. No joke. Great food, service, etc. Joe's isn't a Chicago original, but it is fantastic and one of my favorite restaurants anywhere. The original is in Miami, and 2 more in Chicago and Vegas. The stone crab are phenomenal (I go medium or select sized), and I think they have the best steaks anywhere. Stone crabs > chopped lettuce, tomato, onion & bleu cheese salad > filet > key lime pie or banana cream pie.
I normally have a beer, then follow it with a pinot. I normally start with stone crab, then finish with the Filet. Best meal ever.
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My wife and I had one of the best meals of our lives at Alinea. It was opened by chef Grant Achatz, who has worked at such places as French Laundry (saw your other question about how you tried to make reservations there), and you can bet that anyone who has ever worked under Thomas Keller would be amazing. Good thing you asked early, because like French Laundry, you do need to make reservations quite a bit in advance. It's literally one of the best restaurants in the world.
Last I was there a few years ago, the prix fixe was $190 and the wine pairing I think was just a bit less (prices may have raised a little over the past few years). Definitely not cheap, but I would go back again in a heartbeat.
When my husband and I visited friends in Chicago last year, they took us on a double date to Girl & the Goat. It was so good! According to my friend who has lived in Chicago for a few years, it's one of the best restaurants in town and I can see why. Very unique dishes and such a lovely place. I guess you could characterize its cuisine has modern American. What shocked me the most was when the bill came, it was less than $200 for four people. We had eaten our hearts out and ordered wine!
Sunil, have you tried eating at Alinea? It's not only my favorite restaurant in Chicago / The Midwest, but it may be my favorite in America.
I have a few recommendations:
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My boyfriend and I had drinks and an appetizer at Gilt Bar before seeing a show. The place is beautifuly lit with dim bulbs that look like candles. The drinks are unique and presented very nicely. We asked the waiter what the best appetizer to have was and he suggested the steak tar tar and boy he was right. Overall the place is very cozy and you definately get a romantic feel. Almost like you're in the movies. Located downtown not too far off Michigan Avenue it's a magical place to take a loved one and feel like its just the two of you in the room.