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Explore These 7 Wonders of the Windy City

Two days into a four-day visit to Chicago and I was convinced. New York may be nifty and Las Vegas might have pizzazz but Chicago is chock-full of enough allures and attractions to keep me going for a month. Fact is, winnowing the wonders of this wondrous city down to sufficiently few to conquer in my short time was no easy task. But I was willing to give it a try.



The sights on Michigan Avenue have earned it the nickname “The Magnificent Mile”. At top, the Chicago Architectural River Cruise sails passengers alongside some of the city’s most fantastic skyscrapers. (Sharon Matthews Stevens photos for VacayNetwork.com)

If Chicago were a tree, Michigan Avenue would form its trunk. The end of the thoroughfare we visited is called the Magnificent Mile, Chicago’s answer to Fifth Avenue.

Think three million feet of retail space — from Neiman Marcus to Nordstrom — and one iconic attraction after another.

We strolled down the street, crossing the Chicago River over the DuSable Bridge, and reaching Millennium Park. Then we reached the Art Institute of Chicago and a concert hall that’s home to the Chicago Symphony.

Welcome to the Cultural Mile.

You’ll be forgiven for thinking you have been transplanted to the Champs-Élysées. After the Great Fire of 1871 destroyed much of Chicago, planners visited Paris and returned inspired by the vision of Haussmann, to design and build expansive thoroughfares like Michigan Avenue. 

A walk on Michigan Avenue — first of the Windy City’s seven wonders — is the perfect way to begin your romance with Chicago.


Halfway through a Chicago Jazz Festival performance in Millennium Park’s Jay Pritzger Pavilion, I decided to put our guide’s assertions to the test.

On an earlier walking tour we had stopped into this Frank Gehry-designed amphitheatre while the guide waxed enthusiastic. “Put seven-thousand people in here,” he said. “Sound system’s so good you’d think the band was in your living room.”

I marched away from the stage — halfway to Soldier Field. Cue horns.

Frank was right. Place is an acoustical (and architectural) wonder.

Between acts, my wife and I further explored the park, stopping beside a huge steel sculpture that looks like a gigantic bean. Hundreds of people crowd around it, snapping a surfeit of selfies.

This is “Cloud Gate”, one of Chicago’s most photographed subjects, and one more addition to Millennium Park, the third attraction in a trio of treats — along with the Pritzger Pavilion and a 3.5-acre urban garden — that helps this downtown oasis clinch the title of the Windy City’s second wonder. 


For years I thought that a masterpiece called “American Gothic” (an overalls-clad farmer holding a pitchfork and posing beside a homely wife) was based on the opening credits of Green Acres, my favorite 1960’s sitcom.

Then I found myself standing before it in the Art Institute of Chicago, realizing it was actually art.

A few minutes later another piece (hardly surprising — 300,000 works of art are sheltered here) caught my wife’s fancy. She’s reflecting on Seurat’s “A Sunday on La Grande Jatte,” a famous work more than eight feet by 10 feet.

Fronting Michigan Avenue, the museum comprises both modern galleries and an august structure that was originally an exhibit hall for the Chicago World’s Fair of 1893.

Might not know much about art but I know one thing about the Windy City’s third wonder. It’s an elegant rebuttal to those naysayers who think this midwest city don’t got no culture.



Family-friendly fun and spectacular entertainment is what’s on offer at the world-class Shedd Aquarium. (Sharon Matthews Stevens photo for VacayNetwork.com)

Right from the start — from the marble entrance with the Corinthian columns to the 360-degree Caribbean Reef — the John G. Shedd Aquarium impresses.

First opened in 1903, it was designed by the same firm that gave birth to the Field Museum (next door) and the Wrigley Building downtown, a neoclassical temple to Neptune.

With five-million gallons of water the Shedd was once the world’s biggest indoor aquarium. It features beluga whales, penguins, and performances at the Abbott Oceanarium. For very good reason I could spend an entire day here and still not tire of its appeals.

That’s because the Shedd’s a whole ocean of wonders.


We sat in the recording studio of Chess Records, listening to blues tunes pouring forth from speakers at one end of a long low room on Michigan Avenue, an atmospheric space rich with history and contemporary entertainment.

The building housing the studio that has been influential in blues and rock ’n roll is also the home of the Willie Dixon Blues Heaven Foundation. Dixon is a blues legend who recorded with the likes of Muddy Waters and Bo Diddley, and his family has inspired and curated the Chess Records visitor experience. It boasts a repository of original instruments, a history of the blues, and a blues garden next door featuring live performances.

Its address is as significant as its legacy: 2120 South Michigan Avenue.

You might recognize it. In the very room where I sat listening to iconic tunes is where the Rolling Stones recorded their first ever instrumental in 1964.

It was called 2120 South Michigan Avenue.


We glided along the Chicago River on a boat called “Chicago’s First Lady” and watched a towering procession of skyscrapers that went on so long my neck ached.

We passed the Tribune Tower, designed to be the world’s “most beautiful office building”; the Wrigley Tower, a masterpiece of art-deco construction; the Trump Tower, a monstrosity he originally planned as the world’s tallest building.

Chicago is the capital of skyscrapers and the best way to see these memorials to both height and hubris is from a comfortable seat in the bow of a tour boat that chauffeurs you on a spectacular excursion into architecture, with a generous helping of Chicago history and culture thrown in.

Seven wonders of the Windy City? If we get rid of Windy City this should just be: Seven wonders?

We’ve seen four times that without even getting off the boat.

But who’s counting?



Lou Malnati’s Pizzeria is an institution in Chicago and one of the first places to introduce deep-dish pizza. (Sharon Matthews Stevens photo for VacayNetwork.com)

On our last evening in Chicago we reclined on the patio of Lou Malnati’s Pizzeria in an area called the Gold Coast.

I was hoping for a different local delicacy (a Chicago-style hot dog) but my wife prevailed, so we indulged in another culinary catch. The deep-dish pizza really is a pie — two inches high, making room for extra cheese, tomato, and whatever else you desire.

It’s no ordinary pizza and Lou Malnati’s is no ordinary pizzeria.

Lou Malnati himself perfected the art of deep-dish in the 1940’s, opening his first eatery in 1971. The restaurant uses cheese from Wisconsin, California tomatoes, and attitude that is all Chicago. Its website says it ships pizza to happy customers nationwide.

On the first bite, I understood why.

“Number seven,” I said, through a mouthful of cheese, gazing out at people marching up and down North State Street in the waning twilight.

“Sorry?” my wife replied.

“Been thinking about the Seven Wonders of the Windy City.”

“Think you’ll get it down to seven, do you?” she said.

She had a good point. The “Bean” sculpture is pretty wonderful. 360 Chicago’s pretty neat. Haven’t even touched on Maggie Daley Park or Navy Pier, for that matter. Maybe she was on to something.

“Just seven wonders,” she added. “Good luck with that.”


Where to Stay: The Blackstone Hotel is the perfect base for exploring Chicago. It’s elegant and historic (the Beatles once performed an impromptu set within its confines) and its Michigan Avenue address makes it the ideal location. Website: www.theblackstonehotel.com. Nightly Rates: Room nights for a weekend in June begin at $500 per day.

Tourism Info: For more details on visiting the city, check out the Choose Chicago website

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