Things to Do
For an overview of Chicago's iconic cityscape, head for the top of the Willis (Sears) Tower or the John Hancock Center. Admire American Gothic and other masterpieces at the Art Institute, then get a waterfront view of the city's past and present on a Chicago Architecture Foundation boat tour. Traveling with kids? Stroll Lincoln Park Zoo (for free!) or spend a day exploring the U505 submarine and other wonders of the Museum of Science and Industry.

Active Pursuits
Explore the miles-long path that hugs the Lake Michigan coastline, then rent a bike or join a pickup volleyball game at sprawling North Avenue Beach. Culturally minded? Take a sculpture-spotting stroll through the Loop to admire works by Picasso and Miró, and walk through the wildly popular bean-shaped "Cloud Gate." Baseball fans can pay homage to one of the last of the old-time ballparks, Wrigley Field; cheer on the Cubbies from the raucous bleachers, or check out the view from the field on a behind-the-scenes tour.

Restaurants & Dining
From haute to down-home, Chicago has restaurants to suit all tastes. Chef Grant Achatz redefined fine dining at Alinea, while his fellow superstar chefs at Charlie Trotter's, Moto, and Spiaggia get global raves. Explore the city's ethnic diversity in Greektown and at Mexican mainstay Frontera Grill. For gut-busting satisfaction, chow down on Chicago-style deep-dish pizza at Gino's East or the original Pizzeria Uno.

Nightlife & Entertainment
The Goodman Theatre and Chicago Shakespeare Theatre are the heavy-hitters of Chicago's vibrant theater scene. Classical superstars take the stage at the Lyric Opera and Chicago Symphony Orchestra, while Second City and iO continue the city's legacy of improv comedy. Catch top pop acts at venues such as the Chicago Theatre, or head to grungy-cool Wicker Park to hear up-and-coming bands.