Discover Chicago beyond the city streets with private outdoor adventures focusing on lakefront trails, parks, and wildlife. Join Teraloom for a unique exploration experience tailored just for you.
More ways to explore the area's outdoor wonders
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Difficulty
moderate
Duration
2–4 hours
Fitness Level
Suitable for participants with average fitness; some light hiking and moderate walking required.
Wildlife
History
Chicago’s park system is one of the oldest in the U.S., designed to provide urban residents with access to natural beauty.
Conservation
Local efforts focus on protecting lakefront ecosystems and maintaining green spaces through sustainable urban planning.
Teraloom
Discover Chicago beyond the city streets with private outdoor adventures focusing on lakefront trails, parks, and wildlife. Join Teraloom for a unique exploration experience tailored just for you.
Teraloom is a Portland, Oregon–based travel operator that lists and offers trips across a broad set of U.S. destinations. The company’s public trip roster covers 44 locations spanning the West Coast, East Coast, Gulf Coast, and Hawaii. Examples from the trip list include Portland; multiple Southern California beach towns such as Newport Beach, Long Beach, Santa Monica, and Huntington Beach; Florida destinations including Miami, Clearwater, Fort Lauderdale, Fort Myers, Destin, Jacksonville, Daytona Beach, and Clearwater; East Coast and Mid-Atlantic ports such as New York (Manhattan, Staten Island, Freeport), Atlantic City, Cape May, Point Pleasant Beach, Rehoboth Beach, Ocean City (MD), Annapolis/Mayo, and Boston; Southern coastal destinations like Charleston, Wilmington (NC), Outer Banks, Galveston, and South Padre Island; plus Pacific Northwest and other cities such as Seattle, San Francisco, and Honolulu.
Teraloom’s trip listings include named locations and, where indicated, different group formats (for example, Atlantic City and Cape May entries include small, medium, and large group options). The brand is featured on The Adventure Collective, which documents Teraloom’s destination coverage and trip offerings. Prospective travelers should consult the published trip listings for specific itineraries, schedules, pricing, group-size options, and booking details. All statements here reflect the trip names and location information published for Teraloom; users seeking reservations or changes should review the authoritative trip pages and booking policies associated with each listing.
Tours Offered
44 trips
Coastal and city destinations
Headquarters
Portland, OR
Portland, Oregon base
Featured On
The Adventure Collective
Editorial feature listed
Group Options
Small–Large
Small, medium, large group options
Check availability for specific destinations and group sizes across the listed locations and follow booking instructions on each trip page.
Stay Hydrated Near Lake Michigan
Lakefront trails can get warm in summer, so bring plenty of water to stay hydrated while exploring.
Wear Layers for Variable Weather
Chicago’s weather can change quickly; dress in layers to stay comfortable during your adventure.
Use Sun Protection
Open areas near the lake offer little shade, so apply sunscreen and wear a hat to protect yourself from UV rays.
Watch for Pedestrian and Bike Traffic
Popular trails can get busy, so stay alert to share paths safely with others.
Reusable Water Bottle
Staying hydrated is key during any outdoor activity, especially along lakefront trails.
Lightweight Layered Clothing
Spring weather can be variable; layering helps you adapt to changing temperatures.
spring
Sturdy Walking Shoes
Comfortable shoes with grip are necessary for varied terrain in parks and trails.
Sunscreen and Hat
Protect yourself from strong sun exposure during summer lakefront adventures.
summer