Cruising Chicago's Lakefront Trail

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Chicago Lakefront Trail at dusk

Timing is everything when it comes to biking Chicago's Lakefront Trail, especially from the comfy seat of a beach cruiser. Sandwiched between the city's legendary skyline and the ocean-like views of Lake Michigan, the 18-mile trail traverses everything from city parks, harbors and a dozen or so beaches to long, uninterrupted stretches of pathway. It is the undisputed champion of Chicago's views. Not surprisingly, it draws both locals and visitors at all hours, sometimes in droves and especially in summer when the beaches are a main reason to come to the city. Knowing when to go can make all the difference in the world.

I was born and raised in the Chicago area and the Lakefront Path, as it's more commonly known, has always been my favorite thing about the city. I've been there alongside the early morning runners and cyclists who rise just after sunrise to log miles sans crowds. I've also caved to the summer beach scene and its shimmery water, despite the mass chaos of pedestrians and wheelers who often don't follow the same rules of the road (Heads up! Watch your back!). I've even been out in the winter when it's almost too cold to smile.

But now, in the sticky heat of the summer, I wanted a relaxed and breezy beach cruiser ride. I decided on early evening, heading out during those magical hours right before and after sunset when the city is both remarkably quiet and totally alive. A big rainstorm had blown through earlier in the day, which made for an unusually desolate but striking scene. I welcomed the open space, set off on my cruiser and jumped on the Path at Lincoln Park for the 6-mile roundtrip ride south to Navy Pier. Follow along my route in the slideshow below.

Cruising Chicago's Lakefront Trail
For the full spectrum of Chicago scenery, I like to start in Lincoln Park, the sprawling lakefront park north of the downtown that’s also home to museums, gardens, a rowing canal and the free Lincoln Park Zoo. New in recent years, the super-green Nature Boardwalk — a legit urban ecosystem buzzing with wildlife — stands out.
Along the Nature Boardwalk, the striking bentwood pavilion always makes me stop, just as with a work of art. Inspired by a tortoise’s shell, the pavilion serves as an outdoor classroom for yoga and more; it’s also a dreamy space in which to take shelter. Both the boardwalk and the pavilion are the work of visionary local architect Jeanne Gang
I breathe a sigh of relief at first sight of the skyline and Lakefront Path. I have never seen it so quiet. (Note to self: Come after a storm to have more space.) At my left, North Avenue Beach offers some of the widest and deepest stretches of beach sand in Chicago. Though it is July, I pedal into a cool breeze.
I take a break at North Avenue Beach, locking up my bike at the Beach House shaped like a giant boat before walking toward the water. Children play on the shore, and I smile at the thought of sturdy Chicagoans: these kids belong to die-hard locals who frequent the beaches no matter if it’s cloudy, chilly or late. 
Castaways Bar and Grill sits on the top deck of the boat-like beach house and is normally teeming with drunken, sun-drenched beachgoers. Tonight, the crowd is more subdued, and the open-air bar looks like a perfect pit stop. I dust the sand off my feet, climb the stairs and order a tasty crab ceviche with an iced tea. 
Chicago is a big city, and you never quite know what you will encounter on the Path. Case in point: pedaling along the long breaker wall south of North Avenue Beach, I saw a group of jugglers and a dancing rollerblader. Just as with Gang’s wood pavilion, I had to stop for a look, lest I cruise right into the lake.

Nearing Navy Pier, I stop at the crescent-shaped sliver of Ohio Street Beach, where I spot a ham of a bulldog and a few other pups. Though it’s not officially a dog beach, most people don’t mind in the off-hours so long as the dogs are leashed. To see them running free, head back north to the dog-friendly Montrose Beach.

One of the neatest things about biking along the Path is how quickly the perspective changes. When I began my ride, the skyline was just a distant view; now, it looms to my right in the shadow of the 100-story John Hancock Center. Looking back over my shoulder, the sun drops behind the now-tiny buildings where I started. 

It is pricey and touristy (Chicago’s number-one tourist attraction, in fact), but there’s a lovely and unmistakable energy to Navy Pier. Originally built in 1916, the 3300-foot pier is home to Chicago’s Shakespeare Theater, several restaurants and bars (including a beer garden where bands play), all kinds of boat tours and Pier Park, where you find the 150-foot Ferris wheel. I like to enter the pier from the back side, where there’s far less foot traffic, riding my bike all the way to the end for close-up views of boats passing.

On the return, I walk my bike down the pier’s main drag and through the throngs of visitors, passing the beer garden and live music from a Smiths cover band, food carts selling funnel cakes and cinnamon-glazed almonds and several boats boarding passengers for a night cruise. I almost always stop at the Ferris wheel; the views from the top are pretty outrageous.

Heading back, I retrace my route but never once feel like I’m seeing the same thing twice. As day turns to night, so does the mood of the lake and the landscape. Looking at the city against the sky, I’m reminded of a night boat cruise from last summer and how the city looked even more exotic from the water.    
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Where to Rent a Beach Cruiser in Chicago

Beach cruiser rentals are found across the city, and rates are pretty comparable ($30 - $35 for a full day), so you only need to decide where you want to begin your ride. There's Bobby's Bike Hike located on the North Side on a slip at the River East Docks (also offering guided tours). There's Bike and Roll at Navy Pier and the McDonald's Cycle Center at Millennium Park. If you plan to overnight in Chicago, stay at one of a handful of cool hotels near the Lakefront that also offer complimentary cruisers to guests. I like Hotel Lincoln as it's just across the street from the namesake park where my ride began.

And for shorter rides in Chicago, the city just launched Divvy, a new bike share program.

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