All Outdoor Adventures
Boating
Chicago, Illinois
Chicago Architecture River Cruise
Cruise Chicago's harbor lasting 1 hour 15 minutes (approx.) with views of Chicago River from the water.
★ 4.8 (17010 reviews)
From $53.70
Illinois guide
Illinois Outdoor Adventure Guide
Illinois has 47 tours across 1 cities, covering Hiking, Day adventure, Cycling, and Boating.
Explore this area
Explore All tours in Illinois, Cycling tours in Illinois, Hiking tours in Illinois.
Plan your adventure
Quick links: All tours in Illinois · Cycling tours in Illinois · Hiking tours in Illinois
Recommended itineraries
2–3 days
Weekend (2–3 days)
Base your weekend in Illinois and mix a highlight tour with one signature activity.
4–5 days
Classic (4–5 days)
Split time between Illinois and another nearby hub to sample multiple activities.
7 days
Deep dive (7 days)
Loop through three regions and layer in longer tours for a full-state perspective.
Top tours in Illinois
Sailing
Chicago, Illinois
Lake and River Architecture Tour
Sail Chicago's bay lasting 2 hours (approx.) with views of Chicago River from the deck of a private or small-group yacht.
★ 4.7 (2440 reviews)
From $49
Sailing
Chicago, Illinois
Lake Michigan Sunset Cruise in Chicago
Sail Chicago's bay lasting 1 hour 30 minutes (approx.) with views of Chicago River from the deck of a private or small-group yacht.
★ 4.5 (1692 reviews)
From $45
Cycling
Chicago, Illinois
Chicago Bike Tour
Cycle through Chicago, linking Millennium Park, on a guided bike route with neighborhood context and photo stops.
★ 4.9 (1189 reviews)
From $60
Food & Wine
Chicago, Illinois
Chicago Walking Food Tour With Secret Food Tours
Taste local specialties while exploring historic downtown around Chicago Loop on a guided walking route.
★ 4.9 (1012 reviews)
From $89
Sailing
Chicago, Illinois
Lake Michigan Skyline Cruise in Chicago
Sail Chicago's bay lasting 1 hour (approx.) with views of Navy Pier from the deck of a private or small-group yacht.
★ 4.4 (951 reviews)
From $33
Sailing
Chicago, Illinois
Chicago Skyline Sunset Sail Aboard a Tall Ship
Sail Chicago's bay lasting 1 hour 30 minutes (approx.) with views of Navy Pier from the deck of a private or small-group yacht.
★ 4.8 (842 reviews)
From $55
Cycling
Chicago, Illinois
Tastes of Chicago Bike Tour
Cycle through Chicago, linking West Loop, on a guided bike route with neighborhood context and photo stops.
★ 4.9 (767 reviews)
From $75
Best time to visit
Tour availability in Illinois varies by operator and activity, so check live calendars and choose dates that match your preferred pace.
What to pack
Plan for comfort and flexibility: bring layers, comfortable footwear, sun protection, and a refillable water bottle. Specific tours may recommend extra gear after booking.