The Matchbox is the smallest bar in the city, and it makes some of the better classic cocktails around. If you roll your eyes when people talk about making friends at bars, come here - you’re in such close quarters that it’s impossible for conversations not to overlap and intersect until you've got a new group of drinking buddies.
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Gibsons Italia, in River West, is the trendy Italian sister spot to Gibsons Bar & Steakhouse.
Piccolo Sogno is a classic Italian restaurant complete with candlelight, white table clothes, and pure romance.
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The Victor Cocktail Bar
The Victor is an intimate cocktail bar in North Center that makes great Old Fashioneds.
The Long Room
The Long Room is a craft beer bar in Lakeview that's great for an early in the game date or catching up with friends.
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