Top City Break Destination: Chicago, Illinois

When rapper Lupe Fiasco branded Chicago the "best city in the whole wide, wide world," he may have ruffled some feathers. Upon closer inspection, there's plenty to back it up: a destination-worthy dining scene; deeply rooted music culture; and soaring, significant architecture. Throw world-class museums and a cutting edge cocktail culture into the mix, and you have the makings of a memorable jaunt.

Hugging the sandy shores of Lake Michigan, where sailboats bobble when weather allows, Chicago is a city of neighborhoods, each one with a distinct feel and intriguing, historic context. Long pegged as a working-class city, Chicago is so much more: a hotbed for top chefs, an epicenter for sports enthusiasts and a source of inspiration for innovators old and new.

Edible adventures can be had along ethnic stretches, such as Devon Avenue, Wentworth Avenue, and Argyle Street, though many of the city's most interesting eats are tucked into unassuming storefronts and found off the beaten path. Culinary tours -- especially those with an insider's bent -- can help acclimate and steer you beyond stereotypes. By the same token, bike, canoe, architectural and even Segway tours reveal points of interest from unique vantage points.

Needless to say, Chicago has its share of tony boutiques; Oak Street and the Mag Mile offer proof of that. But it's also a hub for local designers; vintage Ukie Village finds; and galleries, salvage and indie music stores galore. Even boozehounds can rejoice, thanks to lauded, city-centered microbreweries and distilleries.

Easy to navigate, Chicago streets follow a grid system, with addresses generally increasing 100 each block. Most of its primary neighborhoods -- to mention, its two airports -- are easily accessible by 'L' (elevated train). Buses and cabs fill in the blanks, which means you can get around with ease.

Jennifer Olvera is a regular contributor to Frommers.com and the author of Food Lovers' Guide to Chicago and Select Chicago.