The New Chicago

By Jason Adams
April 3, 2010
Nathan Kirkman
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.

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.


The Wit
201 N. State St.,, doubles from $179, drinks from $8


The Wieners Circle
2622 N. Clark St., 773/477-7444, dogs from $3.50

2119 S. Halsted St.,, entrées from $19

615 W. Randolph St.,, entrées from $14.50


The Art Institute of Chicago
111 S. Michigan Ave.,, $18

Office of Tourism Visitor Information Center
77 E. Randolph St.,, Chicago Greeter tours free

Wendella Sightseeing Co.
400 N. Michigan Ave.,, tours from $24


739 N. Clark St.,, drinks from $9

The Whistler
2421 N. Milwaukee Ave.,, drinks from $8

Plan Your Next Getaway
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A Place for Everyone

DUDE RANCH Our suggestion: Lazy L&B Ranch, Dubois, Wyo. Guests stay in log cabins and spend their days riding horses and communing with goats at the petting zoo. You'll love: Singing cowboy songs by the fireplace., six-night package with all meals and activities from $1,475, kids 12 and under from $1,325. SKI RESORT IN SUMMER Our suggestion: Keystone, Colo. Rafting, fly-fishing, hiking—this winter destination is teeming with summer activities. You'll love: River Run Village's one- to four-bedroom condos are just a three-minute walk from the town's shops and restaurants., one-bedrooms from $129 a night. OLD-TIMEY LAKE TOWN Our suggestion: Mackinac Island, Mich. At this car-free getaway on Lake Huron, the activities haven't changed much over the years: biking, swimming, and eating ice cream. You'll love: The suites and cottages to suit groups of any size at Harbour View Inn., doubles from $149 a night in summer. BEACH RESORT Our suggestion: Sullivan's Island, S.C. Gentle waves and the occasional dolphin offshore make this beach a favorite with kids. You'll love: The wide range of cottages and houses that you can book through local agents at Island Realty., two-bedroom cottages from $1,300 a week. THEME PARK Our suggestion: Walt Disney World. With six parks and a dizzying array of places to shop, eat, golf, and swim, Florida's mammoth complex is the ultimate crowd-pleaser. You'll love: Disney's Saratoga Springs Resort & Spa, where nine people can stay in a tree house., from $555 a night. WATER PARK Our suggestion: Wisconsin Dells. The "Waterpark Capital of the World" has 21 water parks, along with dry-land activities like mini golf and rock climbing. You'll love: With an arcade, a cinema, and a paint-your-own-pottery studio, Kalahari Resort is a hit with kids., doubles from $130 a night. CRUISE Our suggestion: Royal Caribbean's Oasis of the Seas. The 2,706 staterooms run the gamut from twin cabins to family suites to swanky lofts. You'll love: "Central Park," an open-air atrium with more than 12,000 trees and plants., seven nights from $729 per person. ALL-INCLUSIVE RESORT Our suggestion: Occidental Grand Xcaret, Riviera Maya, Mexico. The resort has a seemingly endless number of rooms (769), restaurants (11), bars (10), and pools (15). You'll love: Guests get discounted admission to swim with dolphins., from $107 per person per night.

Ask Trip Coach: Family Reunions

READERS' TOP QUESTIONS How in the world do we decide where to go? As with all things family, the key word is compromise. The goal is to find a place that will make 15 or (Lord help you) 50 very different people happy. First step: Include everyone. Throw out 10 possibilities in a group e-mail, rank them, and see what rises to the top. That's your winner. Second step: Keep your eyes on the prize. This is a reunion, and the best destinations have broad appeal (see eight of our suggestions on the following page). A range of activities and distractions (golf, spas, hiking) is essential; the toddlers aren't going to want to play 18 holes every day, and Aunt Myrtle probably isn't up for scaling a rock face. The best options need to be budget sensitive. The most expensive part of any trip tends to be lodging, so consider destinations that allow you to tackle it creatively—sharing rooms, splitting up among hotels of varying star levels, renting one big house. Whatever you decide, establish a central place where folks can gather casually over coffee or corn on the cob. Any suggestions on divvying up costs and duties? Remember in The Godfather when the five families come together to work things out? Do that. Gather household heads and hammer out who's in charge of what and how everything will be paid for. Try to foresee complications (Who gets the master suite? Shouldn't they pay more?) and come to a fair arrangement ahead of time. A suggestion for one of the murkiest areas: food costs. Have each family put $50 or $100 into a reserve that will go toward basics (ketchup, eggs, bread, ice pops, Diet Coke). Then, because we all know what too many cooks can do to the soup, put each family in charge of one night's dinner for the entire group, including shopping and paying for whatever's on the menu. Everyone else gets that night off. Above all, be clear about little details, every step of the way. It may seem anal, but spelling everything out will help your group avoid confusion, resentment, and the very real possibility of somebody dropping the ball on something as important as making dinner. How do we prevent tensions from flaring up and, at the same time, make the reunion actually fun? If there's one golden rule for family reunions, it's this: Don't overschedule. One group activity per day, max. The goal is to create memories—the good kind. Since the kids will probably be the most entertaining part of the vacation, ask them to put on a talent show, host a dance contest, or act out every part in the circus. They'll have fun, and—most important for the adults—they'll be occupied for days. If you're staying in a place with a private gathering room, throw a party there. Fill tables with snacks and family albums. Seeing as you're on location, take advantage of your numbers (group rate!) to do something vacation-y: Charter a boat to a secluded island for a picnic, for example, or book a guide to take you on a hike in the rain forest near your resort. PLANNING TOOLS Start your pre-trip conversation here. Post-reunion, use the site to share photos and relive memories. Book dozens of hotel rooms and flights at once, often at a discount, and dig through tons of destination ideas and planning tips. Find hotels where the rooms are baby-proofed, the properties have jungle gyms, and the activities won't be deemed lame by teenagers. Investigate locations, themes, games, food, budgeting, and any other reunion-related topics. SANITY SAVERS When your reunion starts to feel more like an endurance test than a vacation, try one of these four increasingly strong prescriptions. Yoga It's amazing what 20 minutes of stretching can do to your outlook. Cell phone Call a friend. Fake a call from "work." Reality TV Watch families far more dysfunctional than yours. Xanax With a doctor's prescription, naturally... YOUR REUNION COUNTDOWN 1 to 2 years out Send out initial inquiry to see who's interested 9 months to 1 year out Discuss, settle on destination 6 to 9 months out Tally a head count, make lodging reservations 4 to 6 months out Buy plane tickets 3 to 4 months out Circulate info on possible activities 2 months out Book activities (ask for a group rate) 1 month out Get a final-final head count, adjust reservations 1 week out Reconfirm reservations, finalize plans for getting to airport 1 day out Pray for good weather

Road Trip: Southern California Coast

Maybe it's the movies. Or maybe it's the press. But to the world, Los Angeles can come off as a Zenned-out land of palm trees, celebrities, and perpetual sun. Meanwhile, for those who live here—all 10 million of us—L.A. is just the opposite, a hard-charging city where you're rarely alone. There are pockets of calm here and there, but the only way to feel as if you've really escaped is to get out of town. And that often involves stresses all its own. Head east and you won't clear the traffic until San Bernardino. Drive south and you'll be skipping between industrial parks and residential developments all the way to Orange County. But go north and stick to the coast: That's where you'll find your peace. One Friday afternoon, my friend Ellen and I leave town en route to Ojai. The small community 85 miles northwest of the city has long been a haven for art-savvy and New Agey Angelenos. Famous ceramist Beatrice Wood—a.k.a. the Mama of Dada—lived here, as did guru Jiddu Krishnamurti, who drew spiritual seekers from far and wide. Ojai's appeal is much less about what's new than what's not. While most Angelenos make the drive in a two-hour shot—keeping to the infinitely more boring inland Highway 101—Ellen and I choose the Pacific Coast Highway. As we clear the L.A. traffic, beaches open up on our left, and the ocean rolls gently in the midday light. Our first stop is Malibu, 40 miles from L.A. but worlds away. Sure, it's home to Hollywood executives, celebrities, and the real-life epitome of California beach culture, Gidget. But that's where the similarities end. Instead of strip malls and parking lots, Malibu has 21 miles of open beaches backed by the sun-soaked Santa Monica Mountains. I can already feel myself loosening up. We ditch the car and stroll along the newly reopened Malibu Pier. Jutting nearly 800 feet into the Pacific, it served as a lookout during World War II. As opposed to the often mobbed alternative in Santa Monica 12 miles south, this pier is nearly empty. Fishermen gather to drop lines into gray-green water. Stand-up paddle surfers glide over the gentle waves at the famousSurfrider Beach, next to the pier. For the first time in weeks, I'm not thinking about work, my kids, or anything even remotely stressful. After leaving the pier, Ellen and I take a detour on Kanan Dume Road and wind our way six miles into the Santa Monica Mountains to Malibu Wines(31740 Mulholland Hwy., Malibu,, tasting from $9). We sidle up to a counter, where we're poured a smooth cabernet made from grapes grown in the 65-acre boutique winery across the road. Out front, tables dot a giant lawn, and two couples are picnicking. North of Malibu the landscape gets wild. Rocky headlands frame unpeopled beaches. PCH snakes by Point Mugu State Park, five miles of rugged coast and canyons that serve as a way station for the monarch butterfly migration in fall. Forty miles on, we roll into the old-school beach town of Ventura. The dinner rush at Andria's, a low-key seafood restaurant, is just starting, and we join the families in line (1449 Spinnaker Dr., Ventura,, entrées from $10). The batter on my fish is nice and light, and Ellen's fried clams are perfectly sweet. By the time we're back on the road, it's dark. We hang a right on Highway 33 toward Ojai, and I can barely see the California oak and pepper trees covering the hillsides. A light rain is falling when we pull into the Blue Iguana Inn, a 15-room boutique hotel with Mexican-pine beds and tile fountains (11794 N. Ventura Ave., Ojai,, from $109). When we wake up, the bad weather has passed. In the morning sun, Ojai's naturally blessed location comes alive: a broad valley dappled with horse ranches and citrus groves at the base of the Topa Topa Mountains. Ellen and I spend the morning exploring the shops, restaurants, and galleries that constitute town (you won't find any drive-through fast-food joints; Ojai has banned them). That afternoon, we set out for Ojai Olive Oil, a small olive ranch outside of town (1811 Ladera Rd., Ojai,, free). Ron Asquith meets us when we arrive. The onetime executive bought the land 10 years ago with his ex-wife, Alice. He leads us inside a barn and shows us the stainless-steel tanks where they press their olives. In the tasting room, Alice introduces us to different flavors of olive oil. We test ourselves, moving beyond the standards: rosemary and mandarin, thumbs-up; garlic, not so much. Ojai is gifted with a forgiving Mediterranean climate, a boon for local farmers—which seems to be everyone. Even Boccali's, a pizza parlor, grows its own produce (3227 Ojai Ave., Ojai,, sandwiches from $10). Ellen and I split an Italian-sausage sandwich and a fresh green salad. At the farmers market, I overhear a lady say she comes there from Ventura because Ojai's produce is superior, and then Ellen and I spot Ron from Ojai Olive Oil and wave hello. We have the impression we know half the town—and in my fantasy version of a simpler life, we do. WHEN TO GO You're almost guaranteed sun in May through October. But even the winter months are mild, with highs in the upper 60s. WHAT TO PACK Board shorts, flip-flops, and totes for farmers market fare. GETTING AROUND Plan your L.A. escape and reentry around the rush-hour traffic, which peaks from 7 a.m. to 10 a.m. and again from 5 p.m. to 7 p.m.

What $100 Buys in...Minneapolis

$8 Rubber bands An eight-year fixture on the stationery scene, Russell+Hazel practically wrote the book on whimsical office wares, adding colorful patterns to everything from file folders to these supersize, 5/8-inch-wide rubber bands. Russell+Hazel, 4388 France Ave. S., $22 Trivet The Swedish-American population in Minneapolis is one of the country's largest, which explains the city's bounty of Scandinavian goods, such as this playful, hand-felted-wool Dala horse trivet. Ingebretsen's, 1601 E. Lake St., $2 Key chain With over 100 kinds of beaded, fringed, and feathered footwear, Minnetonka Moccasin has cornered the market on suede slippers since 1946. Our pick: the pocket-size, 2 3/4-inch mini-moc key chain (it comes in its own tiny box!), a subtle way to sport the style. Love From Minnesota, 178 IDS Center, 80 8th St. S., $9 Honey Ames Farm owner Brian Fredericksen considers each jar of honey a snapshot of an area's botanical identity. Varieties are produced at his 17 Minnesota hive sites, and each is named for the predominant nectar-source plant; the Basswood yields floral notes and mint. Mill City Farmers Market, 704 S. 2nd St., $10 Bath soak A natural-products trailblazer since 1868, J.R. Watkins's southeastern Minnesota apothecary turns out chemical-free concoctions like this bath soak made from sea salt and lavender oil, packaged in sweet containers with old-time labels. Patina, 2305 18th Ave. NE, $38 Wooden robot Twin Cities architect William Dohman took reclaimed wood from area construction and demolition sites to create his series of Block Bots—a nice alternative to today's high-tech toys. (This two-inch-by-four-inch model was an oak spindle in a former life.) ILikeYou, 501 1st Ave. NE,