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Stroll through historic Chicago

Chicago Urban Exploration Cruises

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Discover the vibrant city of Chicago on our selection of 7 urban exploration 2025 city tours. Chicago, known for its stunning architecture, iconic skyline, and rich cultural scene, offers a myriad of experiences waiting to be explored. Delve into the history of the Great Lakes as you cruise through Lake Michigan, admire the natural beauty of Georgian Bay, and witness the thundering Niagara Falls. Whether you choose a relaxed small ship cruise or a more active archaeological site visit, our tours cater to a range of preferences. Explore the cultures of Chicago, enjoy wine tasting, and immerse yourself in urban exploration activities. Join us on a journey that unveils the magic of the Great Lakes and the fascinating city of Chicago. To start planning your adventure, contact one of Adventure Life's tour specialists for help planning your next seamless trip.
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    • Chicago
Mackinac Island, Michigan
from $6,799
OBC
EXPLORE

All Five Great Lakes

Chicago to Toronto - 11 Day Itinerary aboard Victory II
  • Visit car-free Mackinac Island
  • Sail through the Soo Locks
  • Explore the Henry Ford Museum
  • Visit Niagara Falls
Starts / Ends
Chicago / Toronto
Activity Level
Variable
Embark on an 11-day All Five Great Lakes cruise aboard Victory II, visiting iconic cities such as Chicago, Detroit, and Toronto. Discover scenic wonders like Mackinac Island and Niagara Falls, exploring rich history and culture along the way.
Cruise Details
0
Enjoy the stunning scenery of Lake Superior
from $6,799
OBC
EXPLORE

All Five Great Lakes

Chicago - Toronto - 11 Day Itinerary aboard Victory I
  • Discover Michigan's Upper Peninsula
  • Explore Detroit's Henry Ford Museum
  • Explore Manitoulin
  • Visit Niagara Falls up close
Starts / Ends
Chicago / Toronto
Activity Level
Variable
Embark on an 11-day Great Lakes cruise from Chicago to Toronto aboard Victory I, exploring cities, islands, and historical sites. Enjoy scenic sailings and unique excursions.
Cruise Details
0
Enjoy the scenery of the Great Lakes
from $7,999
EXPLORE

Great Lakes and St. Lawrence Seaway

Chicago - Montreal - 13 Day Itinerary aboard Victory I
  • Visit Willis Tower in Chicago
  • Explore the Henry Ford Museum
  • Visit Rock and Roll Hall of Fame
  • Discover Toronto's culture
Starts / Ends
Chicago / Montreal
Activity Level
Variable
Set sail on a 13-day from Chicago to Montreal, experiencing the Great Lakes in style aboard the Victory I. Each day offers unique experiences, from scenic sailing to cultural explorations, making this a one-of-a-kind adventure through North America's freshwater treasures.
Cruise Details
0
Explore the rocky shores and clear waters of Lake Superior
from $9,699
Save $7000
EXPLORE

Great Lakes and Thunder Bay

Chicago Roundtrip - 16 Day Itinerary aboard Victory II
  • See Chicago’s stunning skyline
  • Take a horse-drawn carriage tour
  • Visit Iron Industry Museum
  • Visit the historic Soo Locks
Starts / Ends
Chicago / Chicago
Activities
Urban Exploration, Archaeological Site Visits, Village Visits
Activity Level
Variable
Embark on a 16-day cruise from Chicago aboard the Victory II, exploring the Great Lakes' diverse landscapes and historic cities. Enjoy horse-drawn carriage tours, visit museums, and explore historic sites.
Cruise Details
0
Stunning Niagara Falls
from $7,999
EXPLORE

Great Lakes and St. Lawrence Seaway

Montreal - Chicago - 13 Day Itinerary aboard Victory I
  • Discover the city of Toronto
  • Visit the Henry Ford Museum
  • Visit Lake Huron
  • Savor local delicacies
Starts / Ends
Montreal / Chicago
Activity Level
Variable
Embark on an unforgettable 13-day cruise from Montreal to Chicago aboard the Victory I, exploring all five Great Lakes. This voyage combines scenic sailing with onshore excursions, offering a unique blend of urban exploration and natural wonders.
Cruise Details
0
Golden light over the Chicago skyline
from $6,799
OBC
EXPLORE

All Five Great Lakes

Toronto - Chicago - 11 Day Itinerary aboard Victory I
  • Discover the diverse food scene
  • Enjoy the vibrant nightlife
  • Visit Niagara Falls
  • Explore Niagara Peninsula
Starts / Ends
Toronto / Chicago
Activity Level
Variable
Embark on an 11-day All Five Great Lakes cruise from Toronto to Chicago aboard Victory I, exploring vibrant cities and stunning natural landscapes. Enjoy historical tours, and scenic sailing on this unique cruise through the heart of North America.
Cruise Details
0
Detroit, Michigan at Dusk
from $6,799
OBC
EXPLORE

All Five Great Lakes Reverse

Toronto to Chicago - 11 Day Itinerary aboard Victory II
  • Explore Toronto
  • Experience Niagara Falls
  • Visit Henry Ford Museum
  • Enjoy a horse-drawn carriage tour
Starts / Ends
Toronto / Chicago
Activity Level
Variable
Set sail on an 11-day All Five Great Lakes cruise from Toronto to Chicago aboard a Victory II. Explore Toronto, Niagara Falls, Cleveland, Detroit, and Mackinac Island, experiencing unique landmarks and vibrant cultures.
Cruise Details
0
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