Chicago—The modern American city

Many consider Chicago the most modern and the most “American,” of our big cities. With mirrored towers stretching up into the skies, icy winds whipping off the colorful lake shores, this birthplace of the skyscraper offers enough promise to attract immigrants and tourists from all over the world.

In the low-slung streets of Lakeview and Lincoln Park, Chicagoans indulge what keeps them warm all interminable winter long: deep-dish pizza, Vienna Beef hot dogs and the reddest slabs of meat. Sports, comedy and music are ubiquitous amongst nightlife options, and from the steakhouses of the so-called Viagra Triangle to the hipster corridors of Wicker Park, Chi-town maintains the sense of edginess that it grew famous for.


Kith & Kin. Try amazing Gulf surf & turf in this Lincoln Park dining scene that combines rusticity with refinement. 1119 W. Webster Ave.

Schwa. This Wicker Park foodie gem is all about Michael Carlson, voted a “Best New Chef” by Food & Wine in 2006. Nine-course meals served over the world kitchen’s rap-metal soundtrack—the best “tasting menu” in the city. 1466 N. Ashland Ave.

Billy Goat Tavern. Underneath the Chicago Tribune Building, the original hangover cure serves greasy cheeseburgers and many beers. 430 N. Michigan Lower Level.


Sushi Wabi. This crowded, noisy, West Loop storefront hot spot has amazing wasabi-butter filet mignon and rolls. 842 W. Randolph St.

The Randolph Street Market Festival. Trawl for distinct antiques, great vintage estate jewelry and cool designer pieces. Open Nov. 20-21, and one weekend a month from May through September. 1350 block of W. Randolph St.


The Drawing Room. A subterranean cocktail lounge that turns out imaginative elixirs. This favorite late-night spot stays pen until 4 a.m. on Saturdays, offering quality late-night fare like bacon-wrapped pork belly and fried avocados. 937 North Rush St.,

Violet Hour. So chic venue for the perfect martinis. 1520 N. Damen Ave.

This post was excerpted from the Wall Street Journal Concierge Insiders Guide to Chicago.

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