Have questions? We're here.
Stroll through historic Chicago

Chicago Bicycling Tours & Trips

Travel made your way ™
Talk with an expert
Build your ideal Great Lakes trip. Call 1.406.541.2677
Start Planning My Trip
Talk with an expert
On these top 3 Chicago bicycling tours, you'll stroll down meandering roads, trails, and bike paths as you take in the Chicago scenery.  A guided small group or private guided cycling tour of Chicago may include bike rides near popular cycling destinations like . Our Chicago bicycling trips start at $6,799 for a 11 days tour and may include leisure cruising, mountain biking, or road biking. Tell us about your ideal Chicago cycling adventure and one of our Chicago travel experts will help you build the ideal bicycling vacation.
Filter (3 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Levels
  • Experiences
  • Activities
  • Ships
  • Destinations
    • Chicago
Explore the picturesque shoreline of Lake Superior
from $9,699
EXPLORE

Great Lakes and Thunder Bay

Chicago Roundtrip - 16 Day Itinerary aboard Victory II
  • See the Door County Maritime Museum
  • Take a horse-drawn carriage tour
  • Stroll Green Bay shoreline
  • Visit the historic Soo Locks
Starts / Ends
Chicago / Chicago
Activities
Biking, Urban Exploration, Archaeological Site Visits
Activity Level
Variable
Sail from Chicago round-trip on a 16-day Great Lakes and Thunder Bay cruise aboard Victory II and explore scenic ports across the Great Lakes. Cruise through Lake Michigan and Lake Superior on a journey full of natural and historic highlights.
Cruise Details
0
Explore Toronto
from $6,799
EXPLORE

All Five Great Lakes

Chicago to Toronto - 11 Day Itinerary aboard Victory I
  • Sail across Lake Michigan
  • Explore Milwaukee's Riverwalk
  • Bike Mackinac Island perimeter
  • Rock out in Cleveland
Starts / Ends
Chicago / Toronto
Activities
Local Market Visits
Activity Level
Variable
Embark on an 11-day cruise aboard Victory I at Chicago’s Navy Pier and cruise across all five Great Lakes. Explore Milwaukee’s breweries, Mackinac Island’s historic charm, the Soo Locks at Sault Ste. Marie, Detroit’s vibrant art scene, Cleveland’s Rock and Roll history, and the power of Niagara Falls.
Cruise Details
0
Explore the rocky shores and clear waters of Lake Superior
from $6,799
EXPLORE

All Five Great Lakes

Toronto to Chicago - 11 Day Itinerary aboard Victory I
  • See powerful Niagara Falls
  • Explore Cleveland’s rock history
  • Tour Milwaukee’s lakefront gems
  • Visit peaceful Mackinac Island
Starts / Ends
Toronto / Chicago
Activity Level
Variable
Cruise the Great Lakes from Toronto to Chicago on an 11-day cruise aboard Victory I. Explore museums, historic districts, and natural wonders while enjoying relaxing scenic days at sea.
Cruise Details
0
1-3 of 3 Results
  • 1

Great Lakes Travel Guide

Top Great Lakes Travel Destinations

Great Lakes Trips by Departure Date

Great Lakes Trips by Duration

Great Lakes Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By

Jess Heuermann Adventure Life employee profile
Jess H
Plan My Trip
We love travel, talk with an expert 1.800.344.6118