The urge to escape the concrete jungle is a natural one. For paddlers, the desire is almost innate, so much so that big cities rarely land on the bucket list. But when you give a city a second look, and start stacking up the number of different paddling options, certain unlikely urban paddling havens rise to meet their skylines.

And when we decided to give Chicago that chance for a longer look, it landed atop that worthy paddling-city list. Urban or remote, relaxing or invigorating--the Windy City yielded memorable yet drastically different paddling adventures, all within a one-hour drive of each other.

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Our five-day flurry to experience the area's most interesting options started, appropriately, at one of the city paddling's scene primary origin points: on the Des Plaines River. In Libertyville--a short 45 minutes north of downtown--local paddlers Greg Browne and Andy Cocallas were eager to join us on a stretch of the famed Des Plaines. This was the river where Cocallas got his start after buying a canoe from "Mr. Canoe" himself: the legendary Ralph Frese, the late Chicago paddling outfitter-organizer-conservationist, who in 1958 started the Des Plaines River Canoe Marathon, the second longest-running canoe race in the country.

"Ralph showed me the Des Plaines by his shop and I got hooked on it," Cocallas said. "I found it a premiere paddle in the northern part of Illinois."

The historic voyageur waterway begins in Wisconsin and snakes 133 miles through protected forests before dumping into the Illinois River. The day we paddled it, the river was at flood stage, allowing unique forays into parking lots, along bike paths and into groves of silver maple trees where the muddy water spilled over its banks. Even at flood stage, the river featured a gentle flow perfect for any level paddler looking for a dose of nature and wildlife.

"I like it because of the remoteness," Cocallas added. "Chicago is so enthralled with metropolitan growth that it's hard to get away from it. You can go out here for an evening paddle and most likely not see another paddler or person out there."

It wasn't the area's only outer escape from the bright lights, either. A rugged adventure awaited in Morris, Illinois, an hour southwest of downtown, where met up with Janée Matteson, the owner of the Kayak Morris campground along the Illinois River. We followed Matteson across the Illinois before tucking into one of her childhood playgrounds: the Mazon River. With family roots in Morris dating back to the early 19th century, Matteson knew the waterway well, the result of a lifetime spent exploring these same waters.

"I grew up fishing, duck hunting and trapping on that river with my father," Matteson said. "I used to put canoes on the Mazon and float through the different branches for discovery."

We got a taste of this 'discovery' first-hand. We portaged around logjams left from recent storms, watched bald eagles and blue herons soar down from the sycamore tree canopies, and enjoyed tasty snacks in the form of the juicy berries from the branches of mulberry trees drooping over the river banks. The backwoods bushwhacking and scampering up muddy riverbanks gave our minds a reprieve from any memories of Interstate 90 traffic, as well as the notion of our proximity to one of the continent's biggest cities.

Eventually the gravity of the city pulled us back in, no paddling trip to Chicago complete without a tour through the canyon. And by canyon, I'm not referring to one bound by limestone and sandstone strata; rather, one formed of steel, glass and concrete.

It was time to paddle the Chicago River.

We launched from the REI Boathouse at Ping Tom Memorial Park along the South Branch to Wolf Point confluence where the two branches meet the Chicago River's straight shot east to Lake Michigan, with a view down "the canyon." Gazing skyward immediately took our breath away.

We needed more. The next day, we floated back down to Wolf Point from Kayak Chicago's launch on the North Branch of the river. As the sun set, we rounded the point and headed into the heart of downtown. We craned our necks to take in the overwhelming views of glass towering above us. The colossal city buzzed as planes, trains and automobiles zoom around and overhead. Mother Nature has a way of making paddlers feel insignificant. Dodging boat traffic in a gauntlet of skyscrapers felt different, but in a similar way, provided that humbling perspective.

To the city-dwellers, we must have looked alien, finding ourselves on the receiving end of many tourists' camera lenses as we continued our paddle toward Navy Pier and Lake Michigan along the "Magnificent Mile," Chicago's famed upscale avenue of shops, landmark buildings and hotels. We laughed at our sudden celebrity status, the mile to the lake flying by as iconic architecture wonder captivated our attention.

Once out on the dusk calm of Lake Michigan, we were back in a place we understood. We'd escaped the city, again. This time, however, we gawked back at the buildings with a new appreciation: the skyline and the natural curvatures of the lakeshore stretching miles in either direction--a juxtaposition that seemed to embody our Chicago paddling experience of immediate man-made wonder, with respite in nature just a few strokes away.

-- This article was produced with support from REI.


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