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re: masha
It would be helpful to know more about the cuisines or locations that interest you. For many area restaurants, 8 is not a particularly large number. With that said, I tend to prefer restaurants with round tables when dining with 8, and that can be harder to find. Many steakhouses will fit the bill, including Gibson's in the city and Myron and Phil's in Lincolnwood. Maggiano's does well with that size, as do most Lettuce restuaurants. Chicago Brauhaus in Lincoln Square also does well with groups. Many establishments in Greektown would not blink at 8. Some finer-dining restaurants would even consider offering private dining areas for 8 depending on your interest and budget.
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