GOLD COAST. Tucked between North Avenue and Oak Street along Lake Shore Drive, the Gold Coast offers some of Illinois's most desired lakeshore property. The neighborhood, known for its architectural history and cultural richness, is home to many of the city's most prestigious and influential movers and shakers. Drop by one of the booming cafés, bars, or shops and see who is out and about.

LINCOLN PARK. Some of the city's trendiest shops, bars, and theaters call this neighborhood home, as does the famous Steppenwolf Theatre Company. Named for the park that encompasses its eastern border, the neighborhood of Lincoln Park runs from Diversy Parkway to North Avenue.

LONG GROVE. Located about 30 minutes north of the city, this charming little town is completely worth the detour. Cobblestone streets lead to charming rows of houses-turned-boutiques that cause you to forget about the ubiquitous places created by corporate America. Delicious eateries adorned with antiques offer everything from fine dining to specialty chocolates to artisan oils. Have a drink in an English-inspired pub to rest your feet after a day of shopping. The Christmas season in Long Grove is particularly delightful and features Old World-style carolers.

MAGNIFICENT MILE. Some of Chicago's best shopping and dining can be found on the Magnificent Mile. Running down Michigan Avenue and bounded by Oak Street to the north and the Chicago River to the south, the area offers the best of things expensive: Consider it the Rodeo Drive of the Midwest. If you seek a trendier, more eclectic setting, go two blocks east to Streeterville, a more hip division of the neighborhood.

OLD TOWN. Home to Chicago's legendary Second City comic troupe, Old Town has many claims to fame. The neighborhood, located between North Avenue and Division Street on North Wells Street, was once a hippie paradise. Now it's home to some of Chicago's best nightlife spots. The demolition of Cabrini Green, a notorious government housing project, has helped make way for cottages and row houses in the now-upscale neighborhood. The area also offers an array of shops, bars, and restaurants.