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Windy City Wonder

Published: 02/06/2012 - Filed under: Home » Archive » 2012 » June 2012 » Destinations » Home » Features » Are You Covered? »

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Chicago, aka The Windy City, The City of Big Shoulders, The City that Works, probably has more nicknames than any other metropolis in America. Once an early frontier fort on the shore of Lake Michigan, it’s a pancake level piece of asphalt where fire hydrants are opened in suffocating summers, and the “Hawk” chills to the bone as it whistles over ice-crusted snow during very long winters. Nonetheless, Chicago, now celebrating its 175th anniversary, is a popular destination for vacationing or to live, work and play.

Chicago is a bi-polar, fiercely competitive city cut in two by Madison Street, an east-west line that begins downtown and stretches to infinity, making North Siders and South Siders for life. It has two of everything – two newspapers, two baseball teams, two airports, two seasons (winter and summer), the “city” and the “burbs,” as well as its movers and shakers scrambling to reach the top. 

 Like the Chicago Bear’s iconic former coach Mike Ditka, now owner of Ditka’s Restaurant, Chicago is as moody as it is glorious. Its pleasant smile and boisterous spirit can turn into a scowl in a moment’s notice. Its mercurial face can be seen in the reflection of its signature Lake – one moment placid blue with sail boats bobbing up and down, and then with short notice, blowing up a furious tempest with angry green eyes and foaming at the mouth. 

It’s an urban jungle where people live and breathe politics, where dead people allegedly vote, and the political machine is oiled and greased, minting out legendary politicos like Mayor Richard J. Daley (1968...”the whole world’s watching”) and Barack Obama, who got his start as a Southside community organizer. 

That Toddlin’ Town

Chicago is a vast sprawling city of 75 officially recognized neighborhoods surrounded by a robust collar of expanding suburbs that eat cornfields for breakfast. It still proudly retains the title Second City, even though with a metro area population of 9.5 million, it’s the third largest in the US. To airborne travelers circling over the tight cluster of skyscrapers spiking upward from the shoreline, the capital of the Midwest looms as a vast city-suburbanopolis radiating endlessly west, north and south from its string of sandy beaches. 

But don’t worry if you happened to forget your GPS. Chicagoans don’t need such bothersome crutches. The town’s laid out in a giant grid. Back in 1908 the city fathers wisely decided to begin all street numbers at the famous intersection of State and Madison, once called “the world’s busiest corner” in the heart of downtown. State Street runs north to south and Madison runs east to west. This simple, but pragmatic numbering system penetrates into the far reaches of the suburbs. 

And don’t worry about getting from here to there either. Chicago has one of the best inter-modal transportation networks in the world to get you anywhere. Nevertheless, in a 2010 Urban Mobility study, Chicago was ranked first in the nation for the worst gridlock in America. So if you’re landing at Midway or O’Hare during the morning rush hour you may want to take an inexpensive rapid transit train to reach your downtown destination, rather than risk getting stuck in traffic. 

The ‘L’ (also variously rendered “El” and “EL”), Chicago’s iconic elevated train scoots rackety-clackety atop neighborhoods, crisscrossing and following streets in a maze of tight turns and straight-aways that give riders treetop views of the city’s neighborhoods and its people that no other mode of transportation can reveal. 

As you near downtown from O’Hare, the train morphs into a subway and suddenly dips down under the Chicago River before emerging once again as the ‘L,’ perched high above street level in The Loop, so-called because the elevated tracks loop the downtown core. Once there, you can walk or cab, or take one of the endless streams of buses to your next appointment.

Chicago is a business-friendly, world class city. From the Gold Coast to Michigan Avenue’s Magnificent Mile to Millennium Park and South Loop, Chicago abounds with top-tier hotels, restaurants, shops and sights to see, all within walking distance of its spectacular lakefront and beautiful tree-lined parks. With time-honored institutions McCormick Place Convention Center and The Merchandise Mart, plus a multitude of other meetings and convention venues, Chicago is a city that works hard to host business travelers from around the world. In May, NATO held its world conference there (you may have seen the headlines) and Chicago leaders continue to boost the city as a site for a future Olympics. 

“Chicago is clearly among the premier visitor destinations in the world,” says Don Welsh, president and CEO of the Chicago Convention and Tourism Bureau, proudly. As evidence of its impact on the local economy, Welsh says the visitor industry is directly responsible for 124,000 jobs, $11.1 billion in direct spending, and $616 million in tax revenue for the city. 

Visitors are drawn to Chicago’s core institutions and attractions like Broadway in Chicago, The Field Museum, Museum of Science and Industry, the Art Institute of Chicago, Navy Pier, and Shedd Aquarium. “Chicago provides unparalleled cultural and entertainment options through every season,” says David Mosena, president and CEO of the Museum of Science and Industry. 

Other popular and less singular institutional year-round attractions include tons of night clubs for all kinds of music, including the classic Chicago Blues, scores of comedy clubs inspired by the famous Second City improv troupe, over 200 critically acclaimed theatre companies where budding actors hone their craft before heading off to Broadway, countless ethnic restaurants, large professional sports venues and art galleries galore. 

The 28 miles of Lake Michigan shoreline offers a boatload of activities including a public golf course, tennis, bicycling, jogging, and picnicking. Or if it’s the young and the restless you want to be near, head down to Oak Street Beach near the Gold Coast, just a stone’s throw from the former Playboy Building. But don’t run and dive into the water without putting a toe in first. The Great Lake is cold, even in July and August. 

If you’re tacking on a family vacation, be sure to take the kids to Lincoln Park Zoo to see lions and bears and more. It’s just a short hop from the beach. And then there are water sports like boating, fishing, or parasailing. Hard to miss, Navy Pier is a hit for adults and kids of all ages with its long strip of gift shops, restaurants, amusement rides, boat rides and a giant Ferris wheel, an exact replica of the one used at the 1893 World’s Columbian Exposition.  

Broad Shoulders

For boat sight-seeing there are dinner cruises, and even architecture cruises for those who want to learn more about Chicago’s famous buildings and world-renowned architects. Considered one of the premier architectural cities in the US, and perhaps the world, Chicago’s skyline is inspiring. It has scores of architectural monument-treasures from architectural trail blazers like Dankmar Adler, Louis Sullivan (regarded as the father of skyscrapers), Daniel Burnham, John Root, Frank Loyd Wright, and Ludwig Mies van der Rohe, who is credited with influencing the bold structural methods and distinctive architectural form of the 100-story John Hancock Center. 

Once back on land, don’t miss the Skydeck at the Willis Tower (until recently, the Sears Building) where you can step out onto The Ledge, the glass-floor balconies suspended 1,353 feet above street level outside the walls of the fourth tallest building in the world. 

Before exiting the Loop, note the Chicago River’s classic draw bridges that serve as backdrops whenever TV news reporters want to establish that they are reporting “live from Chicago.” Prior to human tinkering, the Chicago River emptied into Lake Michigan at the present day intersection of Madison Street and Michigan Avenue. Comprising a system of rivers and canals with a combined length of 156 miles, the Chicago River is notable for literally putting Chicago on the map as the link between the Great Lakes and the Mississippi Valley waterways. 

In 1848, civil engineers reversed the flow of the river away from Lake Michigan to improve sanitation. If you happen to be in Chicago on St. Patrick’s Day, don’t miss seeing the river dyed green for the special occasion. The city has a powerful Irish heritage and a few celebrants have been known to take a personal day off to celebrate what seems to be a de facto city holiday. 

Also not to be missed is the Chicago Water Tower, one of the few structures that survived the Great Chicago Fire of 1871. Local legend has it that Mrs. O’Leary’s cow kicked over a lantern, setting the whole city ablaze. 

Work Hard, Eat Hearty

As “The City of Neighborhoods,” Chicago has an international flavor for every palate. For starters, there’s Greek Town, located on the Near Westside on the other side of the Chicago River, loaded with restaurants serving up great food at great prices. Like many other major cities, Chicago has its Little Italy and Chinatown too, all within a short distance from downtown. With the great influx of immigrants to the Windy City, the mega Taste of Chicagofood festival held in mid-July in Grant Park is a great way to sample food from around the world. 

Chicagoans take their food seriously. After all, when there’s six months of winter, what else is there to do but eat, drink, and argue about who has the best hot dog or deep dish pizza? These specialties have their own cult followings. Chicago expats, no matter where they live, are never satisfied with the hot dog or pizza that is offered in faraway places. When they find each other, they complain about how they can’t get a decent hot dog or “real good pizza.”

The Chicago-style hot dog is traced back to the late 1920s when it was sold by merchants on the late lamented Maxwell Street, a famous flea market that has since succumbed to urban renewal. Today, an authentic Chicago Dog is a kosher-style, all-beef frankfurter that is either steamed or water-simmered. Served inside a poppy seed bun and ordered with the “works,” it’s topped with yellow mustard (ketchup is taboo), adorned with chopped white onions and bright green sweet pickle relish, poked with a dill pickle spear, weighted down with tomato slices or wedges, spiced up with pickled sport peppers, and given a dash of celery salt. Placed reverently on a sheet of wax paper in a red net-plastic basket, a side of fries keeps it warm company. 

Chicagoland touts more hot dog restaurants than McDonald’s, Wendy’s, and Burger King combined. To Chicagoans, Coney Island hot dogs are for wimps. If you have some time, catch the “EL” and go see a Cubs game at Wrigley Field, one of America’s most scenic ball parks, sit with the “bleacher bums” in center field (no ties allowed) and order a hot dog and a beer. 

Chicago-style, deep-dish pizza is another Windy City food ritual that cannot be missed. The origin of the deep-dish pizza is the subject of legend. Some believe the recipe was created in 1943 by owner Ike Sewell of Pizzeria Uno in Chicago. But others say it was the restaurant’s pizza chef, Rudy Malnati, who developed the secretive recipe. We may never know for certain, but the fact is Malnati left Uno’s to found his own deep-dish pizza restaurant. 

Served in a piping hot, 3-inch iron skillet on a wooden board and eaten with a knife and fork, deep-dish pizza is known for its thick buttery crust and copious amounts of mozzarella cheese, tomato sauce and other carefully layered ingredients. Check out these grand-godfathers of deep-dish pizza, listed in no special order – Pizzaria Uno, Lou Malnatis, Ginos East and Giordanos. Newcomers like Pizono’s Pizza and Pasta, founded by a younger generation of the Manalti family, are jockeying for position. If you leave the city without having stuffed yourself with a deep-dish pizza, you’ve left a good part of Chicago behind.

Now that you know how to get around Chicago, there’s one last piece of advice when talking with Chicagoans. It’s on the order of calling San Francisco, “Frisco.” No one but outsiders calls it that. Same goes for “Chi-town.” It’s pronounced “shy-town” and not “Ch” as in chicken. 

Compared to its gritty, “if you can make it here, you can make it anywhere” image, you’ll find that Chi-town is a clean and laid back city. It’s the hometown of a passel of famous citizens like the late John Belushi, his actor-brother Jim, Jack Benny, Bill Murray, Ernest Hemingway, actor John Cusack, Oprah Winfrey and Bo Diddley.But if you like to work hard, play hard, eat hearty and drink hearty, then Chicago is – as those famous lyrics have it – your kind of town. 

Ralf Jackson Walters ( is a Chicago expat living in Winston-Salem, NC. 

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