The New Chicago

Art parks, boutique hotels, a booming food scene, and a sitting President—the Windy City has come into its own recently. For an expat Chicagoan, it's all change he can believe in.

Visitors flock to Millennium Park to check out a hit parade of architectural sights, including the Nichols Bridgeway, where the view captures some of the city's most famous buildings

(Nathan Kirkman)

I was 14 when I made my maiden voyage sailing Chicago's not-so-high seas. Sure, my first job aboard the Wendella Sightseeing boats wasn't exactly manning the capstan—it was actually manning the "pop stand," working 12-hour weekend shifts slinging orange soda and potato chips to the likes of sock-and-sandaled Japanese and German tourists. But I was seeing Chicago from a totally new perspective: drifting up the Chicago River past the Merchandise Mart and the Sears Tower, back through the Chicago Harbor Lock, and out onto Lake Michigan, where I'd take in the entire city skyline as a real-life postcard, the frenzied din fading into a calm hum as we cruised toward the horizon. And it sure as hell beat the pounding I took during the week at my three-a-day freshman football practices.

Over the next few summers, my role with Wendella would grow, and my duties varied from handing out brochures to crowd control, so I was alternately hawking rides to Michigan Avenue's passersby and making orderly passengers out of them.

Graduation from high school marked my graduation to deckhand and took me from part-time to full-time to all-the-time. My days and nights were spent displaying my lasso-like rope-handling skills tying up in the lock, offering wry asides and keen insights on various points of interest, and loading young couples, grandmas, and school groups onto the double-deck Wendella and the single-deck Sunliner. (If you've ever seen The Break-Up, Vince Vaughn does a pretty good turn as me aboard a Sunliner-esque boat near the movie's end.) When I moved away from Chicago in 1995, I'd become something of an expert on the Windy City.

Over time, however, Chicago and I grew apart. A few short months after I moved to San Francisco, my mom was diagnosed with, then soon died from, cancer. I came to resent my hometown for what it was and what it represented to me: a constant reminder that I'd never again have a mother to return to.

In many ways, I became a stubborn ex to Chicago. I doubted that it could grow beyond our deep and loving, but nevertheless youthful and immature relationship. I was convinced I was the only one of us who was really evolving.

After a certain point, though, I realized I was being not only unfair, but silly. I thought it was time I got to know Chicago as it really is today.

Clean start. Fair shake. New beginning.

I decided to take a trip back there not as its spurned son, but as a hopeful tourist.

Standing on Upper Wacker Drive, the wide downtown thoroughfare that winds along the south side of the Chicago River, I felt as if I were seeing some futuristic version of the city. The river walks, once largely forgotten, teemed with restaurants. Across the way, where the Sun-Times building (a low-slung mid-century monstrosity) once stood, now ascended the gleaming new Trump International Hotel & Tower Chicago—a 92-story sparkling rocket ship that redefines the upward limits of the Magnificent Mile's skyline. And at a nearby dock, a fleet of snazzy yellow Checker Cab–style water taxis and a couple of shiny new double-decker tour boats zipped in and out, a far cry from the more modest Wendella boats I'd left behind years ago.

As I headed south on Michigan Avenue, blending in with the other summer tourists, Chicago's most recent transformation hit me in the form of T-shirts, buttons, and bumper stickers: change has come, they told me. The city that for years prided itself on the accomplishments of Mike Ditka and Michael Jordan had a lot more to be proud of these days, namely our first African-American president.

The area that is now Millennium Park had always been a curious eyesore, a place we were led through carefully on Cub Scout field trips. The mishmash of parking lots and railroad tracks didn't blend easily with the more manicured Grant Park along the lakefront nor with the classical beauty of The Art Institute of Chicago, the northernmost of the remaining world-class buildings created for the 1893 World's Columbian Exposition.

These days, however, the park is completely transformed. To find my way around, I first called the Office of Tourism Visitor Information Center on Randolph Street to arrange a free 60-minute tour with official Chicago Greeter Janice Rosenberg. Our first stop was the Frank Gehry–designed Jay Pritzker Pavilion, a sleek new outdoor performing arts addition to the older and larger Petrillo Band Shell in nearby Grant Park. Millennium Park, Janice told me, has been deemed an art park, and in proof of her point, she led me across the BP Bridge and over to Cloud Gate, a kooky metallic outdoor installation by British-Indian sculptor Anish Kapoor that is known locally as "the Bean." I might have been the tour guide once, but given all the new sights, I clearly had a lot to learn.

GROWN-UP CHICAGO

BACK TO THE FUTURE

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