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Friends of the Chicago River canoe guides paddle toward the French Rennaissance-style Wrigley Building (centre) and Trump Hotel on the left.Blair Cosgrove/The Globe and Mail

A canoe trip through Chicago's industrial parks and historic downtown? In my quest for quirky, this was a no-brainer. I would see the city's great architecture without the gridlock and exhaust fumes endured by tourists who rubberneck from the asphalt. It would be simple, fast and environmentally friendly.

Or so I thought. What transpired was an almost carnal encounter with the best and worst of a big metropolis, a sensory overload with a surprise ending.

In a town that boasts everyone from John Dillinger to Hugh Hefner, Oprah Winfrey to Barack Obama, I learned that Chicago's most fascinating personality is the Chicago River. It's one of America's most polluted waterways. And it flows backward.

"Keep your mouth shut," said my guide Chris Parson. He was commenting on what I should do if I fell out of the boat during our three-hour trip. Chris volunteers with Friends of the Chicago River, a non-profit group that works to protect the river, partly through educational paddling tours. I could have taken an easier route – there are several architectural boat tours that offer visitors a great view – but I wanted something that would bring me closer to this notable waterway while still providing lots of design insight.

According to Friends of the Chicago River, Chicago is the only major U.S. city that doesn't fully disinfect its 1.2 billion gallons of daily sewage that is dumped into the river. Up to 10 per cent of the dangerous bacteria is left untreated. And depending on the time of year, almost all of the Chicago River's water comes from sewage plants like the one just north of our starting point in Clark Park.

Oblivious to this, or maybe in defiance, a shirtless father and son were casting on the shore beside us, two small fish in their bucket. As I Googled the nearest hazmat suit retailer, Chris promised me that the river would get cleaner as we moved toward the city centre, 10 kilometres south.

The Chicago River is neither big nor renowned but without it, the city and its bounty of architectural beauties would not exist. For hundreds of years, it brought in the people and materials that built the city, and it still takes out the trash – sewage, industrial waste, abandoned pet alligators and 18 kilograms of green food colouring that civic officials dump into it every St. Patrick's Day – stoically enduring every sort of humiliation. In more pristine environments, paddlers know the sound of laughing water, but what they hear in Chicago is more a burbling martyr's lament, a river gagging on a 24/7 gavage of garbage.

The relationship between Chicagoans and their watercourse never ran smooth. Until 1900, the river flowed into Lake Michigan, from which people drew their drinking water. But soon the river was carrying raw human waste into the lake, and typhoid was becoming as common as kielbasa in a town with a massive Polish population. In 1900, engineers made the river flow backward, and it still does.

The dying wasn't over: In 1915, a steamboat, despite being moored to a downtown dock, capsized and drowned more than 800 people who were mere feet from helpless onlookers. It's hard not to view this as a spectacular, surprise counterpunch from a river that was fed up.

At a temperature of 39 C, our canoe trip was a feverish, surreal experience. At first our boat edged past lots of man-made debris, including a plaid orange sofa that looked as vulgar in the water as it must have once looked in someone's living room.

Soon the gunk gave way to leggy blue herons on the banks, a stout kingfisher in the cottonwoods, a sleek peregrine falcon and a fat carp breaking the surface to oxygenate the languid water for the 70 fish species found within.

Chris has paddled and defended the river for decades, viewing it through a more philosophical, hopeful lens. "I marvel that the water we are on will be in the Gulf of Mexico within five days," he said. "We wouldn't do the things we've done to this river if we had to go out tonight and catch a fish to eat for dinner. This water mimics the circulatory system inside of us, carrying nutrients that sustain the larger landscape. It's the lifeblood of our existence, something we have to protect."

The river's days as Chicago's Charlie Brown may be coming to an end. It's finally getting some love. Each year the Friends of the Chicago River and private tour operators teach thousands of paddlers about the waterway and the ravishing architecture that soars up to 110 storeys above it. Plus, new water-quality standards have finally been approved that will see wastewater disinfection implemented within the next few years.

As we floated along under more of Chicago's 38 movable bridges, the water became cleaner even as grassy riverbanks gave way to the man-made landmarks I had come to see. I marvelled at the cornices and "Chicago windows," the old Montgomery Ward warehouse and the art deco Merchandise Mart building. At 4.2 million square feet and 25 storeys high, it is still one of the largest commercial buildings on the planet and, in my opinion, the world's largest piece of art. Near the Kinzie Street Bridge the air was perfumed with sweet smells from the nearby Blommer Chocolate factory. Mea culpa – I worsened the river's chemical cocktail with a few drops of my saliva.

The eye candy continued. The modern Willis (Sears) Tower, Trump Tower, the Marina City, plus all the aging beauties that are still rocking their original style: the Wrigley Building, the wedding cake-shaped Jewelers Building, the LaSalle-Wacker building and the Tribune Tower, which contains stones from famous structures all over the world, including the Taj Mahal, the Parthenon, the Alamo and the Great Wall of China.

Finally, Chicago's man-made achievements were eclipsing the river's sad story.

With that soaring architecture above and reflected on the water's surface below, I was seeing the heights of Chicago's achievements, and the collateral damage. The great buildings appeared to me like a bouquet of slender historic bricks-and-mortar masterpieces, each as unique and detailed in its ornamentation as any flower.

For them we can thank the enduring, tenacious Chicago River.

IF YOU GO

Friends of the Chicago River offers professionally guided group canoe trips along several sections of the Chicago River, including moonlight outings to the Skokie Lagoons. All transportation and equipment is provided. Cost: $45 (U.S.) a person. Private outings can also be arranged. Visit chicagoriver.org, call 312-939-0490 or e-mail friends@chicagoriver.org.

For an easier river run book a more traditional boat tour to see the best of the city's buildings. Most run daily until mid-November. Notable operators include: Chicago River Architecture Tour – board at the Wendella Docks, 400 N. Michigan Ave., tickets from $12 to $25 (U.S), wendellaboats.com; and the Chicago Architecture Foundation River Cruise – board at the Chicago First Lady docks, 111 East Wacker Dr., $38, cruisechicago.com/architecture_tours.

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