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You can eat for $15 a person in Greektown. Plus, most of the restaurants in Greektown have free valet parking. We often used to pile into cars and head to Greektown from HP when I was in law school.
I know you said you wanted Italian or American, but I can't think of any Italian or American places that are better at accommodating a big group for that price.
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re: SuzMiCo
It is a chain, but you might want to try Buca di beppo (Rush and Grand). I've never eaten there, so maybe other Chowhounds can offer their opinions on the food. I have, however, heard that it is great at accommodating groups since they offer family style dining. From the menu, it looks like the Large size entrees serve 4 people and range between $20-30, so it meets your price range.
http://www.bucadibeppo.com/menu/defau... -
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re: veee
The discussion on Hyde Park at www.chowhound.com/topics/119212 mentions an Italian place in Bridgeport called Franco's Ristorante that might work for you. Its Metromix listing is at http://chicago.metromix.com/restauran...
Another option is a deep-dish pizza place; both Giordano's and Edwardo's have locations in Hyde Park (and the Medici is still there, of course).
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re: veee
Both Bruna's and Tufano's are in the City of Chicago, just not exactly downtown. Tufano's is in the Little Italy neighborhood near the Rush Medical Center/ UIC campus. Bruna's is in the "Heart of Italy" district. At $15/person, you are not going to find much downtown, except for perhaps pizza.
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