Wayne Tower

Eschewing a car or cab to emerging from the darkness of Lower Wacker Drive – one best discovers, on foot, the sites of Chicago.

Wayne Tower
“Wayne Tower” as viewed from La Salle street. (Photo by: Harrison Shiels)

When walking became America’s pandemic pastime, Chicago stepped up as the best American city to stroll. A river runs through it and there is the big, broad border of Lake Michigan forming its east side. There is plenty of green space in Grant Park and space with sights in Millennium Park, too. The varied design combination of classic buildings and modern skyscrapers make the city a giant architectural art gallery. Eschewing a car or cab to emerging from the darkness of Lower Wacker Drive – one best discovers, on foot, the sites of Chicago.

Swissotel a Splendid Start

Old school arrival by train into Chicago’s restored and developing Union Station means emerging to street level in the heart of town to begin an urban adventure. Swissotel stands right over the river and looks over the lake on East Wacker, and, itself, has architectural, all-glass allure. “Our hotel was built by famed architect Harry Weese and his 44-story, triangular design is pointed out on every architectural tour,” said Ted Selogie, Swissotel’s general manager.

It’s fitting the Chicago Architecture Center is virtually next door and is an opportunity to ogle the innovation of engineering and urban design. I admit to using the treadmill in Swissotel’s 44th floor penthouse fitness center, but otherwise my exercise was all steps in sneakers on Chicago’s sidewalks, which I could easily spy from my suite. Looking down I laid eyes on Lake Michigan to the right and the river running through the city to the left, and peering past the Wrigley Building I could just about spot the patio seating at River Roast, a restaurant in which you can watch the water from every seat. There’s plenty to see, too, as the Chicago Architecture Foundation’s First Lady cruise boat goes by having weekend 90-minute departures from right in front of Swissotel.

“Chicago’s history started at the mouth of the river. We cruise all three branches of the river and we go right out to the Chicago lock so you can get a nice skyline photo of the city. It’s the number-one ranked river cruise in the city in part because our tours are led by docents who tell passengers about the city of Chicago. They do it as a labor of love,” said Captain Tom Hacker.  

River Roast Chicago
Every seat has a view of the water at River Roast. (Photo by: Harrison Shiels)

Looking Down on the Skydeck 

It was a one-mile stretch of the legs to Willis Tower – once the world’s tallest – from Rover Roast, but walking off the Lobster Burger and Bee’s Knees craft cocktail (gin, blanc vermouth, lemon, honey and sage) by chef Cedric Harden was important if I was going to empty my stomach for another of Chicago’s memorable meals: a decadent dinner of deep-dish pizza at the famed Lou Malnati’s back on the Gold Coast (an eventual two-mile walk from Willis Tower.) The walk south was fun, though, as one of the surprise highlights was a great view up LaSalle Street of “Wayne Tower,” actually the Chicago Board of Trade Building, used in the Dark Knight Batman movies.

A quick stop at historic, Epcot Center-like, Italian Village Restaurant sitting at Al Capone’s table for a glass of courage-creating Chianti – pulled from a cellar housing more than 100,000 bottles) made the 103-story elevator ascent up Willis Tower visit to Skydeck Chicago less scary but no less exciting. The attraction allows visitors to step 4.5 foot outside the building on a glass-enclosed, inch-and-a-half-thick see-though ledge.

Italian Village Restaurant Chicago
Capone and countless celebs chowed here. (Photo by: Harrison Shiels)

“You can look straight down…and you get 50 miles of visibility from the tower. The sun actually sets four-minutes later from up here than it does on the ground,” explained Randy Stancik, Skydeck’s creator and general manager. Depending on their fear of heights, some people crept cautiously out onto the ledge while some jumped up and down, but everybody took selfies.

Chicago Willis Tower
Look down on the ledge from 103 stories high. (Photo by: Harrison Shiels)

Peering at the Pier

Lake Michigan laps against the Chicago’s Shoreline Trail, which stretches 18 paved miles along Lake Shore Drive beyond Oak Street Beach, with Navy Pier to the south. It made for a good morning sunrise walk before heading onto 50-acre Navy Pier, which is a mile from Swissotel but, given at 3,300 feet long and multiple stories tall, looks as if you could reach out and touch it from your room. In addition to water views, the Centennial Ferris wheel, shops, a park, convention space, pavilion, bars and restaurants, various tourist boat tours board at the pier including the Shoreline Sightseeing cruise which floats passengers out into the lake for a 40-minute panoramic view of Chicago’s landmarks and skyline along with historical and current commentary.

Chicago River
Set sail on Lake Michigan or the Chicago River. (Photo by: Harrison Shiels)

If you don’t hop aboard, you can hoof out to the end or hop to the top of the pier for the view. The newest and snazziest restaurant on Navy Pier is Offshore Rooftop and Bar, an all-weather indoor-outdoor patio perch on the pier’s third floor. I settled onto the southward-facing outdoor veranda near the fire pits.

Kathleen Jenkins, manager of Offshore Rooftop and Bar, visited with me for a spell in the sun as the ships slid by. “In addition to the tourist boats we have the harbor nearby. And we’ve got the locks here going onto the river. I feel here at Offshore it’s like being on a boat or a yacht. All the fun and none of the seasickness,” she said. Offshore would be the deck of a very a big ship. “We are the world’s largest rooftop bar according to the Guinness Book of Records. We have over 50,000 feet of useable indoor-outdoor space. Even when you sit inside you have an outdoor vibe, and you can’t get a better view of the city. And on a clear day you can even see Michigan and Indiana from here.”   

Swissotel Navy Pier
Swissotel’s splendid sweeping view of Navy Pier. (Photo by: Harrison Shiels)

Rooftop Revelry at Joy District

It was 1.3 miles west back across Michigan Avenue and its shops past the Wrigley Building and the Tribune Tower to the River North area to one of Chicago’s other memorable rooftop experiences: “The Roof” at a facility called “Joy District.” The urban open-air bar on Hubbard Street, with its’ flowered couches and string lights is better known for nightlife and therefore, instead of sunlight, the panoply of office lights in the skyscrapers tower over the trendy, year-round rooftop.

Eileen Johnson, one of the managers, showed me around, which is no small task given the size scope of the diverse facility. We got our steps in, for sure, as she led me through the six distinctly decorated, themed restaurants and bars under that rousing roof. We walked from a small-bites sports bar to a Midsummer Night’s Dream-style room seemingly made for weddings and rehearsal dinners. And as flowery as that venue was, the venue above it was gothic and dark. The ground floor Hubbard Inn was the kind of speakeasy, roaring 20’s-style space on might have encountered in Chicago’s pesky prohibition; but there is nothing understated about “The Club” a multi-tier nightclub with acrobats, floating light fixtures and striking artwork.

Joy District Chicago
One of Joy District’s diverse club choices. (Photo by: Harrison Shiels)

Old Style and a Cheezborger 

Eataly, a half-mile away, is three-stories tall – but entirely Italian-themed. From cappuccino to cannolo to chicken carbonara the operation embraces and offers the comfort cuisine Chicago craves.

“Italian food, when the ingredients are great, Italian food is a celebration of simple food. Italy’s food is simple, easy to executive and not terribly expensive. All around the world there are people who crave this food,” said Eataly’s manager Jason Goodsmith, who lapsed into Italian at the most passionate parts of his conversation.  He so-riled my appetite that the next morning while walking along and under Chicago’s “El” train, when I encountered Gene and Georgetti, the old-school Italian restaurant on the corner, I asked for a Peroni instead of a latte with my brioche.

Of course, beer was the order of the day when while walking underground on Lower Michigan Avenue where the Billy Goat Tavern hides in the shadows but brings in the characters. Columnist Mike Royko, its location steps from the newsrooms of the Chicago Sun Time and Chicago Tribune, and a Saturday Night Live television bit shined a light into this cave of a bar where a bottle of Old Style and a “cheezborger no Pepsi, Coke” hit the midday spot like no other windowless, throwback of a bar could. It’s an authentic Chicago experience worth seeking out…or stumbling across whilst walking the Windy City.

Cheezborger Chicago
The subterranean cheezborger classic. (Photo by: Harrison Shiels)
Breakfast beer Chicago
Breakfast beer? Si beve bierra. (Photo by: Harrison Shiels)

Plan ahead, if you prefer, at ChooseChicago.com

Read more of Michael Patrick’s work at The Travel Tattler, or contact him at [email protected]

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