Webster's Wine Bar, Chicago

You can learn a lot about Webster Wine Bar from the drink list. It's an epic 20-pager, and it's mostly wines, organized by country, region, and hue. The list make it clear this is a truly international wine bar that just happens to be in Chicago—vintages hail from Lebanon, France, Australia, and other far-flung places, as well as offering craft spirits and beers. There's a lot more to the story, though. Below, some FAQs.

How did it all begin?

Flashback to 1994: Husband-and-wife duo Tom MacDonald and Janan Asfour started a simple wine bar typical of those common in southern Spain. The wine list was small; the bar's food menu consisted of cheese, charcuterie and pizza from an electric pizza oven. Since then, though, the bar's purview—both its food and its wine—has grown dramatically.

Who's this sommelier?

Jeremy Quinn, who was named a 2012 "Sommelier of the Year" by Food & Wine magazine. Equally impressive: he's visited many of the vineyards where his wine comes from. On the eatery's website, he shares photos from his adventures in Burgundy, Alsace, and other European locales.

Is there food?

Yes. It's easy to put together cheese and charcuterie pairings—say, Brie Fermier and duck rillettes—but chef Aaron Mooney also whips up a variety of small plates, such as salt cod croquettes and burrata with roasted beets.

Is it pretentious?

No. The bottles could please a wine connoisseur who calls his glasses "double-monocles," but the staff makes the vintages accessible to wine newbies, too. If any one adjective applies here, it's "cozy"—the couches and lounge areas make it a natural spot for a relaxed date.