Question:

I'm going to Chicago next weekend - Any suggestions for a nice place for dinner Friday night?

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I'd like to go to more of an upscale place. Would prefer a steakhouse, new American or Italian fare - but nothing is off limits. The plans for Friday night are just dinner then we'd like to head to a lounge-y type place for drinks (no clubbing after heavy eating)! So if you have any suggestions that would be great, too!

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If you are around little Italy I would go to Francesca's on Taylor. It is very nice inside and the service is awesome. There is always parking right on Taylor or you could have Valet there. After ward, go across the street to WineBar. It is a great lounge with a classy atmosphere. There are plenty top shelf wines, beers, and spirits. The only problem is that after you eat at Francesca's you might not be able to get out of your seat... The food is HUGE!!
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That whole city is filthy. Really, it is. I was there for 9 months and saw nothing but trash. It's even rated last in the US on this report cited below.
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Ruth's Chris Steak House got started in Chicago. Great place to eat, but expensive.

I had a cold beer and a couple of red hots at the Cubby Bear once (right across the street from Wrigley Field), and that's my idea of fine cuisine.

Enjoy the trip!
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The Rain Forest Cafe dah
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I think Harry Carry's would be a good choice for you. They have Italian/American fare, and it's not TOO expensive. Naturally, anything in the city is expensive. BOO to the person who said the city is filthy. The city is actually VERY clean considering how large it is. We have lots of flowers and grass downtown which makes it quite nice.
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For a fabulous meal, go to Fogo de Chao. It's a Brazilian steakhouse and the selection/cuts of meat are terrific. It's all you can eat for one price and their salad bar is amazing. It's not cheap, but I guarantee you will not be disappointed.

http://www.fogodechao.com/
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Weber's Grill.....great steaks and sides. And then pick either of the two Blue Chciago clubs..both are nearby.
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Go to the Chop House. The food is great, the atmosphere is nice and it's got a pretty cool gangster theme. It's pricy and will be busy, but call for a reservation. You will love it!
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I assume downtown Chicago - Gibsons no doubt, mortons as a second.

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So drinking and talking, i dunno, could stay at Gibsons, go to the hyatt regency downtown hotel bar(s)

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I love Gibsons, but am more of a Portillo's kind of guy. There is a Portillo's downtown.

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I am assuming you have about $600. to spend on food and drinks and taxi.
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Chicago is know for it's fantastic sushi. The best and mostt modern/ unique sushi place is Japonais. It is amazing and the also have other asian foods, not just japanese. http://www.japonaischicago.com/

If you want Italian, I would have to suggest La Scarola. It is very upscale and authentic and everything is very fresh.
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Go to Carmine's on Rush St. It's an Italian restaurant and very very good food. Also, I am sure you will enjoy people watching on Rush St!
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Gino's East in downtown has great pizza or Pizzeria Uno. The Berghoff has great american fare.
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at the rainforest cafe their food rocks
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Rainforest Cafe been their many times great food
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Fogo de Chao. Someone else suggested it as well but I have to second it; you will not be disappointed. Not only is the food fantastic, perfect for meat lovers, but the service is superb as well. You will never want for anything while you are there. Make reservations.
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Blue Water Grill

http://chicago.metromix.com/restaurants/...

other places to go to are:

Bin 36

Redlight

Sushi Wabi

Blackbird

Avec

Afterwards go to the W Hotel on Lake Shore Dr for drinks.
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I agree with most of the answers above - except, however, for the Rainforest Cafe.  Its awesome if you are twelve or under, though.

The Chop House is kinda touristy - you  wont find too many Chicagoans in it.

I'd recommend Joe's Steak and Seafood - if you can get in.  One of the best restaurants I've been in a long time.  Fantastic steak, as well as stone crabs.

Gibsons is an obvious city type choice.  Tough reservation.  Upscale Italian- for really upscale, Id think of Spiaggia.  Carmine's and Rosebud on Rush are good too.  Tavern on Rush has good food and a fun vibe.
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Unlimited funds??

160Blue - fantastic, and Michael Jordan owns it.
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Check out The Melting Pot, it's a fantastic fondue restaurant!!  If there are two of you, you could do the 'Decadence for Two" which includes:

Appetizer: Cheese Fondue  (You choose what style cheese) with pieces of bread, vegetables, and apples to dip.

Salad: You choose what style

Entree:  Variety of different oils to cook your meats, fish, and poultry in.  Ranging from teriaki steak, marinated chicken, lobster, shrimp, stuffed ravioli, and much more!

Dessert:  Chocolate Fondue (You choose what style chocolate....from dark chocolate, milk chocolate, white, cookies and cream...etc...  they have a wide selection of chocolates.

The Decadence for Two runs about $90, depending on what styles you choose.

Wherever you decide to go, Enjoy!!
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