Chicago is often celebrated for its architecture, deep-dish pizza, and world-class museums, I can say that the outdoor adventures in Chicago left me as impressed as any skyline view. The city is blessed with Lake Michigan, the Chicago River, and sprawling green spaces that invite visitors to step outside, breathe deeply, and play.
I’ll share in detail three outdoor activities I personally experienced during my time in Chicago—activities that pushed me out of my comfort zone and into nature. Then I’ll recommend four more adventures that either came highly recommended by locals or I researched extensively for my next trip.
I’ll cover everything:
• How to get there (from airports, Union Station, or downtown hotels)
• Booking platforms and tips for discounts
• Services, facilities, and safety details
• My personal reflections—real moments of excitement, awe, and sometimes awkwardness
• Pros and cons of each activity
This is not just a list—it’s a narrative of my time in Chicago, meant to help you craft an itinerary that balances city exploration with authentic outdoor fun.
Part I: Outdoor Adventures I Personally Experienced
- Kayaking on the Chicago River
Location: Chicago Riverwalk, multiple launch points (Urban Kayaks, Wateriders, Kayak Chicago)
How I Got There: From my hotel near Millennium Park, I simply walked down to the Riverwalk. From O’Hare, you’d take the Blue Line to Clark/Lake and walk (about 50 minutes).
The Experience:
I booked my kayak through Urban Kayaks on their official website. They offered a sunset tour for around $65, which I chose, and it turned out to be one of the most unforgettable experiences of my trip.
Paddling under bridges while skyscrapers glowed above me was surreal. The tour guide explained bits of history—the Great Chicago Fire, the transformation of the river’s flow, and stories of iconic buildings like the Wrigley Building and Tribune Tower.
Halfway through, I paused my paddling and just floated. The water was calm, the reflection of neon lights rippled, and the city’s hum surrounded me. It was one of those goosebump travel moments where you realize: “I’m here, in Chicago, living it.”
Services & Facilities:
• Life jackets and paddles included.
• Lockers available for small belongings.
• Bathrooms nearby along the Riverwalk.
Pros:
• Breathtaking views of Chicago’s skyline.
• Knowledgeable guides.
• Tours available day or night.
Cons:
• River traffic can be intimidating with water taxis and tour boats.
• Pricey compared to a simple rental (cheaper DIY options start at $30).
Personal Reflection:
This activity gave me a new perspective—literally—on Chicago. The river is not just a body of water, but a vein of the city, carrying stories, history, and energy.
- Paddleboarding on Lake Michigan
Location: North Avenue Beach, 1600 N Lake Shore Drive
How I Got There: From Union Station, I grabbed the #151 bus, which dropped me close to the beach. It was about a 25-minute ride.
The Experience:
I’ve paddleboarded in tropical places, but doing it with Chicago’s skyline in the backdrop was something special. I rented from Chicago SUP, paying $35 for an hour. The first 10 minutes were a little shaky—Lake Michigan can surprise you with its waves—but once I found balance, the experience was exhilarating.
I paddled out far enough to see the John Hancock Center perfectly aligned with the water, the sand buzzing with beachgoers behind me. At one point, a seagull landed nearby, almost as if to join my little floating escape.
Services & Facilities:
• Rental included board, leash, and life vest.
• Lockers and bathrooms at the beach.
• Lifeguards on duty during summer months.
Pros:
• Gorgeous views of skyline + lake.
• Affordable rental prices.
• Good workout and relaxing at the same time.
Cons:
• Lake Michigan waves can be rough.
• Summer weekends are crowded.
Personal Reflection:
This was my favorite “fitness adventure” in Chicago. Balancing on the paddleboard while gazing at skyscrapers made me feel like I was bridging two worlds—urban energy and natural calm.
- Cycling the Lakefront Trail
Location: 18-mile trail along Lake Michigan
How I Got There: I rented a bike from a Divvy station near Navy Pier for just $3.30 per ride (or $15 for a day pass).
The Experience:
Cycling the Lakefront Trail is the best way to see Chicago’s natural and urban beauty in one sweep. I started near Navy Pier, passed through Grant Park, cruised past museums like the Shedd Aquarium and Adler Planetarium, and eventually made it north toward Lincoln Park.
The trail was lively with joggers, families, and fellow bikers. At one stop, I parked my bike and dipped my toes in the lake at Oak Street Beach, feeling both refreshed and adventurous.
Services & Facilities:
• Bike rentals everywhere (Divvy app is very user-friendly).
• Multiple restrooms and cafes along the trail.
• Dedicated lanes for bikes vs pedestrians.
Pros:
• Affordable, accessible, and scenic.
• Can be as short or long as you want.
• Great way to cover many attractions.
Cons:
• Gets crowded on weekends.
• Watch out for collisions on busy summer days.
Personal Reflection:
Cycling the Lakefront Trail gave me a sense of freedom. The wind from the lake, the view of the skyline, and the movement of people all around me—it was Chicago in motion.
Part II: Outdoor Adventures I Recommend
- Sailing on Lake Michigan
Charter a sailboat from Navy Pier (about $75–100 per person for group sails). Locals rave about the sunset cruises, where the city lights up behind you. - Rock Climbing at Maggie Daley Park
This unique outdoor climbing wall ($20 rental) sits against the backdrop of skyscrapers. Friends told me it’s both a workout and a thrill. - Jet Skiing from 31st Street Harbor
For around $120 an hour, you can speed across Lake Michigan with the skyline in full view. It’s pricier but unforgettable. - Kite Flying at Montrose Beach
Families love this spot for wide-open skies and lake breezes. It’s a cheap, joyful activity that locals swear by.
Booking Platforms & Discounts
• Urban Kayaks, Kayak Chicago: Best for booking kayaking and SUP online directly.
• Divvy App: For affordable bike rentals.
• Groupon Chicago: Often has discounts for sailing, jet skiing, or adventure combos.
• Choose Chicago: Good for checking seasonal events and free outdoor activities.
Spending time outdoors in Chicago transformed the way I saw the city. At first, I came for the architecture, the food, and the culture, but what I found was something much deeper: a city in constant conversation with its environment.
Kayaking on the Chicago River made me feel as though I was paddling through history. I thought of the workers who built the bridges, the engineers who reversed the river’s flow, and the generations of Chicagoans who lived with this waterway. At the same time, I was right there in the present—surrounded by neon reflections, boat traffic, and laughter echoing from the Riverwalk.
Paddleboarding on Lake Michigan tested me in a different way. The lake is vast, powerful, and sometimes unpredictable. Balancing on my board while the skyline stood tall behind me reminded me of life’s delicate equilibrium: strength and vulnerability, chaos and calm, all happening together.
Cycling the Lakefront Trail tied everything together. The trail carried me from bustling beaches to quiet patches of green, from iconic landmarks to hidden corners. At moments I was exhilarated, racing along with the wind in my face; at other times, I simply coasted, watching children build sandcastles or fishermen cast lines into the water.
The recommended activities I didn’t manage to try—sailing, jet skiing, climbing, and kite flying—still linger in my imagination. They remind me that Chicago’s outdoor adventures aren’t something you check off a list in one trip. They’re a reason to return, to see the city again in a new season, under a new sky, with fresh energy.
What truly struck me is how Chicago manages to blend the pulse of an urban metropolis with the freedom of outdoor adventure. In many cities, you have to leave downtown to feel connected to nature. In Chicago, you can walk out of a skyscraper, grab a kayak paddle, and be on the water in minutes. You can finish a business meeting and then cycle beside the lake, trading the buzz of traffic for the rhythm of waves. You can indulge in deep-dish pizza at lunch and burn it off paddleboarding by sunset.
I’ve learned that the best cities don’t just impress you—they invite you to play. Chicago does exactly that. Its outdoor experiences are not staged or manufactured; they’re authentic, rooted in the geography of the Great Lakes and the spirit of its people.
So, my advice to any first-time visitor or even a seasoned traveler: don’t let your Chicago itinerary be confined to museums and restaurants alone. They’re wonderful, of course, but step outside—onto the river, into the lake, along the trails. That’s where you’ll feel the soul of Chicago.
And when you’re there—paddling, pedaling, balancing, or simply breathing in the lake breeze—don’t forget to pause. Look around. Smile at the skyline. Listen to the gulls. Let the water lap against your paddle. Those are the moments you’ll carry home, long after the trip ends.
Because Chicago isn’t just a city to see.
It’s a city to experience, embrace, and adventure in.
