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.
We then strolled through the meticulously laid out Lurie Garden, reminiscent of New York's new High Line park in its use of wood and native perennial plants, and past the downright Blade Runner-esque Crown Fountain, where kids were beating the heat as the 50-foot-high interactive video installation of changing faces spit water on them. We continued on to the slim, tailored span of the Nichols Bridgeway, which extends beyond Millennium Park over to the new Renzo Piano–designed Modern Wing of the Art Institute.
After my time with Janice was up, I wound my way up to the second story of the Modern Wing, where the view of the northern skyline from the window was like a perfectly framed living photo, showcasing the new Trump Tower, the Prudential Building, the John Hancock Center, and the Aon Center. I stood there and tried to piece together what this might have looked like in 1995. Maybe not quite so pretty.
This fit of nostalgia gave me a hankering for my old hot dog haunt from the Wendella days, Gold Coast Dogs, on State Street, which I was sad to discover has been taken over by a 7-Eleven. Thankfully, The Wieners Circle up on North Clark still served a perfect char dog. I asked the pleasingly grouchy woman behind the counter to "run it through the garden" to make it a proper Chicago-style hot dog: a grilled Vienna Beef dog on a poppy-seed bun with mustard, onions, relish, pickle spears, tomato slices, celery salt, and (only in Chicago) spicy little sport peppers. Sometimes tastes can never quite be recaptured, but this was better than I remembered.
One of my blind spots as a former tour guide was always the quality of the local hotels. After all, if you're a native, how would you know? And with my father still living in the western suburb of Oak Park, even on visits back I never got the chance to sample Chicago's growing boutique-hotel scene. Just as important (if not more), I had completely missed the rooftop bar movement, which has hit the city with particular verve.
Eager to see what was out there, I asked around. Along with the outside bar at Zed451 in River North, which has a Venice-Beach-cool-meets-Upper-Peninsula-wood-paneling vibe, the most recommended cocktail lounge was the Roof. Just my luck that it sat atop the boutique Wit hotel, which was not only convenient but very nice for the price. My CB2-like room was larger than my apartment back in New York and had a kitchenette, a rain shower, and a sleeper sofa. When I left the city, this part of State Street was, at best, an afterthought; now it's a destination in its own right. I convinced a few old friends to meet me at the Roof for a before-dinner drink, where we sat among neat and attractive urbanites and overlooked the city on all sides.
If the Roof at the Wit hotel is post-work professionals, The Whistler, a newish mixology-style cocktail bar in the up-and-coming North Side neighborhood of Logan Square, is more rock and roll. I had landed there on the advice of a music publicist named Dana who is much hipper than I am. She had wanted to show me "where the locals hang" before we shot down the Kennedy Expressway to a restaurant called Nightwood in Pilsen, a historically Mexican neighborhood on the Near South Side that for years has been a burgeoning area for local artists (my little sister included). Our three-hour dinner at Nightwood, the first of what's sure to be many foodie spots in Pilsen, included biscuits with honey butter and sea salt, watermelon and arugula salad, chicken liver agnolotti, goat steak, and a smoked trout BLT.
A different night, I tried out Avec, in the West Loop, which is another of Chicago's dining hotspots. The space evokes the horizontal beauty of local hero Frank Lloyd Wright's Prairie School reimagined through a Dutch Modern lens. Because Avec doesn't take reservations, the wait was two hours (leaving plenty of time to make good use of the curbside bar). Once inside, however, a few friends and I went to work on plates of boar sausage, half-roasted chicken, roasted dates, and chewy trofie pasta with duck and sardines. As I sat back, letting the food coma sweep over me, it was a comfort to realize that even as I'd expanded my culinary horizons to the food-crazed cities of San Francisco and New York, Chicago had been growing its own worthy restaurant scene. We'd both changed over the years, sure, but it was nice to know that we'd changed in similar ways.
Like me, Wendella has also gotten up to speed with the times: The once all-cash business now takes credit cards and has a website and a Facebook page. The little clubhouse office is gone, replaced by a slick glass ticket window and even an express ticket machine. The 10:30 a.m. sightseeing trip I led so many times now has an "architectural tour" option.
As the boat pulls away from the dock at the base of the Wrigley Building, heading west down the Chicago River, old and new commingle; the facts I knew are revised. Marina City, a set of twin corncob-shaped towers featured in a stunt sequence in Steve McQueen's The Hunter, is now home to a Smith & Wollensky steak house. When I used to give tours, I'd say, "The Merchandise Mart is so large it has its own zip code: 60654," but now Sarah, our tour guide, tells me that the zip code has incorporated some of its surrounding areas. The Apparel Center, which used to be a giant, largely windowless slab of a building, had more windows punched out of its sides to become the new headquarters for the Sun-Times. The gold-leaf-topped Carbide & Carbon Building is now...a Hard Rock Hotel. And, rumor has it, the black-steel-and-glass Willis Tower, formerly known as the Sears Tower, will soon be painted silver by its new owner—all 1,450 feet of it. As we drift up the river, I realize that I am not reconnecting with Chicago. I am simply, after all these years, finally connecting with it.
201 N. State St., thewithotel.com, doubles from $179, drinks from $8
The Wieners Circle
2622 N. Clark St., 773/477-7444, dogs from $3.50
2119 S. Halsted St., nightwoodrestaurant.com, entrées from $19
615 W. Randolph St., avecrestaurant.com, entrées from $14.50
The Art Institute of Chicago
111 S. Michigan Ave., artic.edu, $18
Office of Tourism Visitor Information Center
77 E. Randolph St., chicagogreeter.com, Chicago Greeter tours free
Wendella Sightseeing Co.
400 N. Michigan Ave., wendellaboats.com, tours from $24
739 N. Clark St., zed451.com, drinks from $9
2421 N. Milwaukee Ave., whistlerchicago.com, drinks from $8