A metropolis sprawling 28 miles along the shoreline of Lake Michigan, the city of Chicago is well-known for its rich history, breathtaking architecture and delicious fare.
But the Windy City has a secret that its 48 million annual visitors often miss out on: It boasts a smorgasbord of recreational opportunities to either escape the concrete jungle or go straight into the heart of it for an urban adventure unlike any other.
If you only have one day in your trip to get outdoors, you can fit a lot into 24 hours in Chi-town. It’s the perfect location to get a quick dose of nature and recreation in America's third most-populous city. We’ll show you how.
Find Serenity on the Des Plaines River
To get the most out of your day, wake up early and head to the Des Plaines River. This iconic Illinois waterway actually begins in Wisconsin before snaking its way south through Illinois' lush hardwood forests for more than 100 miles, and flowing just west of Chicago before joining the Kankakee to form the Illinois River.
The Des Plaines River is well-marked, and there are put-in locations every few miles along its winding river banks. We put-in at Independence Grove Forest Preserve, about 45 minutes north of downtown Chicago, and paddled about eight miles downstream until reaching the Captain Daniel Wright Woods Forest Preserve in Vernon Hills. You can, of course, extend or shorten your paddle depending on how you’re feeling that day.
The river takes you past an array of flora and fauna, including vibrant Silver Maple trees along the banks, beaver sightings and Great Blue Herons soaring overhead. While you're never far from civilization (you'll even see a house designed by famed architect Frank Lloyd Wright) this slow-moving river gives a much-needed reprieve from the hustle and bustle of city life. For those that prefer terra firma, the 56-mile Des Plaines River Trail parallels the waterway for runners, bikers or hikers.
Bike the 606 Trail
With hundreds of trains arriving and departing daily, Chicago is the railroad capital of the United States. Of course, not all rail lines are still in service. Take a trip back in time on one of Chicago's now-converted railway-tracks-turned-bike-path, the 606. The recreational trail was opened to the public in 2015 and follows the old Bloomingdale Line, an elevated train line which used to transport industrial goods for over one hundred years, beginning in the 1870s.
Rent a bike at the Divvy Bike Station (they have bike docks located throughout the city) and begin your journey at Walsh Park, the east trailhead. While not as famous as Chi-town's lakefront bike routes, the 606 gives bicyclists, runners and walkers a unique glimpse at the old factories and warehouses that this railway and city once depended on, as well as vibrant communities including Logan Square and Humboldt Park, where the spirit of Chicago carries on.
Standup on Lake Michigan
Cool off from the summer heat with a late afternoon paddle on Lake Michigan. Take a short drive to Montrose Beach, which also boasts a local skate park and various sports fields.
Save yourself the headache and spend a couple bucks on parking; free parking is hard to come by here during busy times of the year. After ditching the car, we inflated our paddleboards and stroked into the massive lake.
For the best views, paddle south around the pier to reach the Montrose Point Bird Sanctuary, where you can enjoy two-for-one views of migrating songbirds and the Chicago skyline – all while standing on Lake Michigan.
Chicago River Fireworks via SUP or Kayak
For the grand finale, it's time for a sunset paddle through the canyon. Of course, this isn't a canyon created from the stratum of limestone and sandstone, but rather one made of steel, glass and concrete.
Simply put, standup paddling or kayaking on the Chicago River is an experience unlike any other in the world.
Starting from Kayak Chicago rental shop on the North Branch of the river, paddle two miles south until reaching Wolf Point – the heart of downtown where the north and south branches of the Chicago River meet to form the "Magnificient Mile," Chicago's infamous upscale avenue that features many of its main attractions and iconic buildings including the Chicago Water Tower, Tribune Tower and John Hancock Center. Gaze skyward for spectacular views of the sunset reflecting off towering glass buildings and to watch the massive city buzzing with life.
After some essential selfies, paddle east along the "Magnificient Mile." Paddling through this towering canyon of buildings is mesmerizing, but keep your head on a swivel. The boat traffic on the narrow river is similar to gridlock on I-90 and the water chop is not for the faint of heart or inexperienced paddlers. Not to mention, while the river has come a long way since its days as a slaughterhouse sewer at the turn of the century, it isn't the type of water you want to swim in either.
We reached the Navy Pier just in time to watch the weekly summer fireworks show (Wednesdays at 9:30 p.m. and Saturdays at 10:15 p.m.). After the dazzling pyrotechnics, we paddled back while still gawking at the brilliant illumination of Chicago's skyscraper canyon.
Once you finally get off the river, find yourself a watering hole of a different variety to enjoy some of Chicago's burgeoning craft beer selections. You've earned it.
All photos by Aaron Black Schmidt.
More “One Day” Content from ASN