Mountain landscape at sunset

Adventure Travel Guides in Chicago

Discover insider guides, hidden gems, and inspiring stories from outdoor enthusiasts

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Showing 5 posts

From Skyline to Shoreline: Biking the Lakefront Trail in Downtown Chicago

Chicagomoderate
5 min

The Lakefront Trail in Chicago offers an irresistible blend of urban energy and lakeside calm. Spanning 18 miles, this bike path invites riders to experience the city’s skyline alongside sweeping views of Lake Michigan, making it perfect for adventurers ready to explore both nature and city life.

May 09, 2025Read more

The Great Lakes Paddle: Sea Kayaking Lake Michigan's Eastern Shoreline

Chicagomoderate
5 min

Paddle the wild edge of Lake Michigan’s eastern shore, from urban beaches to remote dunes. This sea kayaking route combines thrilling water challenges with moments of stillness among forests and sandy coves. Ready your kayak for a practical yet immersive adventure that tests your skills and connects you with one of the Great Lakes’ fiercest natural forces.

May 09, 2025Read more

Lake Michigan by Paddle: Urban Kayaking with Chicago’s Skyline in Sight

Chicagomoderate
5 min

Experience Chicago from a fresh perspective as you kayak on Lake Michigan, navigating its wide-open waters with the city skyline as your constant companion. This urban paddling adventure balances calm waters with practical insights to help you plan your perfect day on the lake.

May 08, 2025Read more

Walking Waukegan’s Lakefront Promenade: A Practical Adventure by Lake Michigan

Chicagoeasy
4 min

Experience a refreshing stroll along Waukegan’s beach promenade, where Lake Michigan’s waves frame every step with breathtaking views and a breeze that challenges your senses. This accessible lakefront walk combines flat terrain and natural beauty, perfect for anyone eager to connect with one of the Great Lakes’ most dynamic shores.

May 07, 2025Read more

Paddling the Chicago River: Urban Adventure Beneath the Skyline

Chicagomoderate
6 min

Experience Chicago from the water, paddling the city’s river as the skyline towers all around. This uniquely urban adventure blends active paddling with sweeping architectural views, offering an accessible route for all skill levels that reveals Chicago’s vibrant heart from a fresh perspective.

May 07, 2025Read more