Urban Adventure Series: Chicago Bike & Brew to Lake Michigan

Article by Erica Zazo

Urban Adventure Series: Chicago Bike & Brew to Lake Michigan

When you live in a place as absurdly cold as Chicago, you have no choice but to embrace the elements — especially when you’re unwilling to sacrifice adventure in the winter. And while Chicago might not be the first place that comes to mind when you think of winter adventure, you’d be surprised how simple it is to explore a wilder side of such an expansive urban metropolis, no matter the season. 

My wife Courtney and I had been itching to get over to Lake Michigan to see the ice formations and, as a bonus, knew we’d also have the lakeshore essentially to ourselves this time of year. 

“A warm cup of coffee tastes better in the crisp air anyway,” I said to Courtney as we lashed our Moonlite™ camp chairs and Moonlander™ portable camp table to the back of our bikes.  

(Well, that’s what I tried to convince myself, at least, as we braced for a frigid 30-degree ride to Lake Michigan.) 


The Moonlander fit perfectly in Courtney’s bike pannier and the Moonlite chairs cinch tight to my back bike rack with the help of two nylon straps. 


Our goal was to set up our own private outdoor cafe at one of our favorite hidden gems on Chicago’s north side: the tip of the rainbow-painted Kathy Osterman Beach pier.  

We planned to set up around the backside of the small light beacon at the tip of the pier, make coffee, and enjoy the view across the lake to the downtown in the distance. I always look forward to the calming peace that the sound of waves lapping against the pier brings, and the allure of Lake Michigan's glacier-blue water under a cloudy winter sky. 

Over 26 miles of Lake Michigan shoreline borders Chicago. In the summertime, bikers and runners flock to the 18.5-mile-long Lakefront Trail that connects 20 sandy beaches, urban green space, and public parks. Between May and August, you’ll find the lakeshore bustling with volleyball players, slackliners and hammock-loungers, family barbecues, and hundreds of acres of protected natural areas like the Montrose Point Bird Sanctuary, Northerly Island Park, and the Burnham Wildlife Corridor. 

In the wintertime, though? Let’s just say the crowds are mostly absent. 

Gear packed and tires pumped, we hit the road from our condo in Lincoln Square and start our three-mile journey east to the lake. We pass through our local neighborhood green space, Winnemac Park, cruise through “Little Vietnam” in Andersonville, and jump onto the Lakefront Trail once we reach uptown. The ease of access to one of the world’s largest freshwater lakes in our own backyard never ceases to amaze me.  

 Riding through the Little Vietnam neighborhood in Andersonville, Chicago. 


I’m a firm believer that Chicago’s mix of cultures, people, and urban nature hidden around every corner is what makes it so special to explore here. 

Traveling by bike through the city is a sensory overload. Rolling on two wheels through any of Chicago’s 77 neighborhoods offers an array of architecture, smells of sizzling food trucks and mom-and-pop restaurants, and a melody of different voices along the way. Our diversity is our strength. 

Over halfway there, we passed a lone slackliner balancing between two trees on the edge of the lake. I’m constantly surprised with reminders like this of just how many outdoor adventurers (like me) exist in such a big city. It makes sense why so many hikers, bikers, runners, anglers — and even slackliners — love living here: Chicago grants access to green spaces and waterways around every corner of the city. The outdoors exist right here within its limits. 


A hardy winter slackliner keeps up the practice even on this blustery day. 
The painted rainbow flag marks our destination: the pier at Kathy Osterman Beach. 


A bright, painted rainbow flag at the end of the pier served as our waypoint. The pop of color is easy to spot against the monotone water and lackluster sky, and provided a cheery boost while marking the finish line for our trip. 

 We made it! Next step: Reward ourselves with some fresh, hot coffee. 


Making our way down the pier, we marveled at the jagged, sculpture-like creations of snow, sand, and ice on the edge of the beach. The lakeshore is a breeding ground for this spectacular type of natural phenomenon where the lake-effect wind and snow molds and freezes waves on the shoreline. 


Frozen waves on the shore of Lake Michigan. 


Only a couple of lone joggers passed us on the pier as we reached the end of the path. Those folks are the last we saw during our private coffee hangout — just the way I like it. I set up the Moonlander™ while Courtney unstrapped the Moonlite™ chairs from the back of my bike.  

  Setting up “camp.” 


“Wow, I’m so glad these chairs have a mesh backing — otherwise they’d take off straight into the lake,” said Courtney. I wholeheartedly agreed.  

Our two mugs, propane tank, teapot, and Nalgene full of water all fit comfortably on our makeshift coffee table, and we gratefully plopped down in the chairs to rest. As we sat, we fired up the propane canister and watched for the steam to rise from the kettle; when it was time, we went through the meditative steps of slowly pouring the hot water over our Kuju coffee and waiting for the grounds to steep.  

Finally, with a warm cup of coffee in our mittens and an endless view ahead, we could relax and enjoy our own little slice of urban nature. 

“Cheers,” we said, in tandem, with a clink of our camp mugs. 



Erica Zazo (she/they) is a Chicago-based freelance outdoor writer. She’s passionate about exploring — and inspiring others to explore — urban nature and lesser-known trails, towns, and destinations. The Midwest is their favorite stomping ground.