River North captures most of the expense-account diners, but the neighborhoods to the west of downtown—Bucktown, Wicker Park, and Logan Square—are where some of the city's most innovative dining occurs. With concepts like the vegetarian-friendly MANA, the pork-heavy Bristol, and dessert-focused Mindy’s Hot Chocolate, West Side restaurateurs serve great food without looking like they're trying too hard. Pick a ’hood and wander on foot—good eating won't be hard to find.

To the east lies Lincoln Park, named for the lakefront park it borders. Often a first stop for recent Chicago transplants moving to the city as well as the permanent residence of families inhabiting pricey brownstones, the popular neighborhood is definitely worth exploring. From a food perspective, it's host to several of Chicago's best restaurants, including Alinea and Boka. On commercial thoroughfares such as Clark, Halsted, and Armitage, you can spend an afternoon bouncing back and forth from great restaurants and cafés to hip shops.