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Top Chicago Cruises & Trips

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Explore these 7 top Chicago cruises for 2024 and 2025. Some of the most popular activities on our Chicago trips include small ship cruises, urban exploration, cruises, cultural, and archaeological site visits. Discover Sault Ste. Marie, Mackinac Island, Chicago, Lake Michigan, and Lake Huron with your expert local English-speaking guides who will show you the hot spots and the off-the-beaten-path hidden gems. We work with only the best small ships that carry under 500 fortunate guests, and we can give you unbiased advice to match you with the perfect ship and perfect cruise for your next vacation. Our Chicago cruises start from $6,799 for cruises of 11 to 16 days. Contact one of Adventure Life's Chicago cruise specialists for help planning a seamless trip.
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    • Chicago
Enjoy the stunning scenery of Lake Superior
$6,799
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
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration
Activity Level:
Variable
Embark on an unforgettable 11-day 5 Great Lakes cruise aboard Victory I, starting in Chicago and ending in Toronto. Stay at a hotel in Chicago before setting sail from Navy Pier. Explore vibrant cities like Detroit and Cleveland, marvel at the natural beauty of Mackinac Island, and witness the …
Cruise Details
0
Mackinac Island, Michigan
$6,799
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
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration
Activity Level:
Variable
Embark on an unforgettable 11-day cruise through the Great Lakes, starting from Chicago’s Navy Pier. Sail aboard Victory II, experiencing iconic destinations like Mackinac Island, Detroit, Cleveland, and Niagara Falls. This unique voyage offers a blend of vibrant city life, stunning natural …
Cruise Details
0
Explore the rocky shores and clear waters of Lake Superior
$9,699
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:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration, Village Visits
Activity Level:
Variable
Set sail from Chicago on a 16-day cruise aboard the Victory II, exploring the rich history and natural beauty of the Great Lakes. Your adventure begins in Chicago, with stunning architecture and world-class dining. Cruise through Lake Michigan and Lake Superior, stopping at iconic destinations like …
Cruise Details
0
Enjoy the scenery of the Great Lakes
$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
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration
Activity Level:
Variable
Embark on a 13-day cruise from Chicago to Montreal aboard Victory II, exploring key landscapes and landmarks of the Great Lakes. Start in Chicago, visiting vibrant neighborhoods and notable sites like the Willis Tower. Cruise through Lake Michigan to destinations like Escanaba, Michigan, and …
Cruise Details
0
Golden light over the Chicago skyline
$6,799
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
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration
Activity Level:
Variable
Begin your 11-day All Five Great Lakes cruise in Toronto, exploring the CN Tower and Royal Ontario Museum. Experience Niagara Falls and the charm of Niagara-on-the-Lake. In Cleveland, visit the Rock and Roll Hall of Fame and West Side Market. Discover Detroit’s history at the Henry Ford …
Cruise Details
0
Stunning Niagara Falls
$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
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration
Activity Level:
Variable
Set sail on a 13-day cruise aboard the Victory II, starting in Montreal and ending in Chicago, as you travel through all five Great Lakes. Begin by exploring the cultural richness of Montreal and Toronto before witnessing the breathtaking power of Niagara Falls. Navigate through the historic …
Cruise Details
0
Detroit, Michigan at Dusk
$6,799
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
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration
Activity Level:
Variable
Experience an 11-day cruise through the majestic Great Lakes aboard Victory II, beginning in Toronto. Explore the wonders of Niagara Falls, Cleveland, Detroit, and Mackinac Island. Sail through Lakes Ontario, Erie, Huron, Superior, and Michigan, each offering scenic beauty and historical …
Cruise Details
0
1-7 of 7 Results
TrustScore 4.9 | 316 reviews
TrustScore 4.9 of 5
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Based on 316 reviews on
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1 day ago
The company representatives were totally dedicated to helping me secure my trip! I was very impressed with how courteous and knowledgeable they were!
Carey Atkins
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1 day ago
Friendly people who ask good questions to make sure your trip is what you want
K.Godinez
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1 day ago
The trip planners at Adventure Life are excellent - very knowlegable, helpful, professional and responsive.
Avi Argaman
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2 days ago
Excellent, friendly, and knowledgeable service and assistance.
Vaughna Cochenour
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2 days ago
Was very easy to come up with an itinerary that included everything I wanted in a trip to Nepal with good communication, prompt service and really felt my needs were considered.
Robert

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