Studying the Skyline: The birthplace of the modern skyscraper, Chicago is the perfect place to learn about -- and appreciate -- these dramatic buildings that reach for the sky. A good way to ground yourself in the city's history is to take an architectural tour -- by foot, bus, bike, or boat.

Getting Lost at the Art Institute: This vast art museum offers myriad places for private meditation. Internationally known for its French Impressionist collection, the Art Institute can also transport you to Renaissance Italy, ancient China, or any number of other worlds.

Chilling Out on the Lakefront: It really is cooler by the lake -- meteorologically and metaphorically. There are 29 miles of lakefront for biking, 'blading, or simply being, so get out there and contemplate Chicago's very own ocean. To experience Chicago to its fullest, don't just sit on the shore; get out on the water for a fresh look at the city. Navy Pier is the place to board a boat that's just your speed, from a powerboat to a tall-masted schooner. Or, if you feel like putting your own wind in some sails, rent one of the boats from the Chicago Sailing Club in Belmont Harbor.

Listening to Music Under the Stars: Pack a picnic and take the train (or drive) to the Ravinia Festival in Highland Park, summer home of the Chicago Symphony, or stay in town to enjoy the free concerts presented in the city's front yard, Grant Park.

Getting the Blues: Here in the world capital of the blues, you've got your pick of places to feel them, from the collegiate atmosphere of Kingston Mines in Lincoln Park, where musicians perform continuously on two stages, to the earthy roadhouse New Checkerboard Lounge on the South Side, where neighborhood locals mingle with the tourists, blues lovers all.

Walking the Walk: You notice the most interesting things when you lace up your sneakers and let your curiosity power you. Explore Chicago's diversity with a neighborhood walkabout; it's one of the best ways to get a feeling for how the people here actually live, from Hispanic families in Pilsen to gay couples on Halsted Street.

Taking in a Show: The stage lights rarely go dark on one of the country's most bustling theater scenes, home to a downtown Broadway-style district anchored by some beautifully restored historic theaters, the nationally known Goodman Theatre company, and the city's resident Shakespeare troupe. But beyond downtown you'll also find a number of innovative independent theater companies, where future stars get their big breaks and the pure love of theater practically leaps off the stage.

Riding the Rails: Find out why the Loop is so named by hopping a southbound Brown Line elevated train (or "the El," for short), and watch the city unfold as the train crosses the Chicago River and screeches through downtown canyons.

Shopping the Town: Chicago may have two baseball teams, but shopping is the national pastime when you're browsing and buying your way up Michigan Avenue or discovering the one-of-a-kind boutiques in Wicker Park, along Armitage Avenue, or in one of the city's other trendy enclaves.

Taking in Some Cool Jazz at the Green Mill: This atmospheric Uptown jazz club is the place to go to soak up some smooth sounds from some of the hottest up-and-coming performers on the jazz scene today. But don't just go for the tunes -- the club, a living museum of 1930s Chicago, is an attraction in itself.

Bonding with the Animals at Lincoln Park Zoo: You have no excuse not to visit: The Lincoln Park Zoo is open 365 days a year and -- astonishingly -- remains completely free, despite many recent upgrades. Occupying a prime spot of Lincoln Park close to the lakefront, the zoo is small enough to explore in an afternoon, and varied enough to make you feel like you've traveled around the world. Most of the exhibits have been renovated in the past few years, making the place look better than ever. For families, this is a don't-miss stop.

Soaking Up Sun at Wrigley Field: It's a Chicago tradition to play hooky for an afternoon to sit in the bleachers at this historic baseball park and watch the Cubbies try to hit 'em onto Waveland Avenue. Should the perennial losers actually win, you can celebrate at one of the neighborhood's many watering holes.

Getting Jurassic: The newest resident of the Field Museum is mighty Sue, the largest T-rex skeleton ever uncovered. Standing majestically in the museum's grand entrance hall, she greets gawkers with a pointy-toothed snarl -- or is it a grin?

Playing in the Sand at Oak Street Beach: If you're staying at a North Michigan Avenue hotel, you can hit the sands of this unique urban beach about as fast as your elevator gets you to the lobby. Of course, you might not want to venture very far into the chilly waters (even in summer), but the scene offers enough people-watching to while away a sunny afternoon.

Exploring the Wright Stuff in Oak Park: Seeing the earliest examples of Frank Lloyd Wright's Prairie-style homes side by side with rambling Victorian villas is an eye-opening lesson in architectural history. The town of Oak Park -- with its funky shops and vibrant community spirit -- makes a great side trip.