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.

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.

GROWN-UP CHICAGO

BACK TO THE FUTURE

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