Studying the Skyline
The birthplace of the modern skyscraper, Chicago is the perfect place to learn about -- and appreciate -- these dramatic buildings. If you're in town for only a short time, get a quick skyscraper fix by strolling through the heart of downtown, known as the Loop, where you'll be surrounded by canyons of stone, concrete, and glass. (To get the full urban experience, visit on a weekday, when the streets are bustling.) If you have more time, take an architectural tour by foot, bus, bike, or boat.

Chilling Out on the Lakefront
It really is cooler by the lake (both meteorologically and metaphorically), and we Chicagoans treat the Lake Michigan waterfront as our personal playground. Miles of parkland hug the shoreline; walk to Monroe Harbor for picture-perfect views of the city or join active Lincoln Park singles for biking or jogging farther north. For an even better look at the city, get out on the water. At Navy Pier, you can board a vessel that's just your speed, from a powerboat to a tall-masted schooner.

Riding the Rails
Find out why the Loop is so named by hopping a Brown Line elevated train (or "the El," for short). Watch the city unfold as the train crosses the Chicago River and screeches past downtown high-rises. Half the fun is peeping into the windows of offices and homes as you speed by. (Don't feel guilty -- we all do it!)

Escaping Downtown
Local politicians like to refer to Chicago as "a city of neighborhoods" -- and, in this case, they're telling the truth. You won't really experience Chicago unless you leave downtown and explore some residential areas, whether it's the historic wood-framed homes in Old Town or the eclectic boutiques of Wicker Park.