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Stroll through historic Chicago

Chicago Cruises & Tours

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Welcome to the Windy City - Chicago, Illinois! Right on Lake Michigan, this beautiful city invites you to visit the many attractions, like the giant mirrored bean known aptly as "The Bean", the Willis Tower or the John Hancock Observatory, the Shedd Aquarium, Navy Pier, or the Art Institute of Chicago.

Chicago is best explored from the water, and our Chicago river cruises and Chicago boat tours are a must-do. Enjoy a relaxing Chicago dinner cruise or set sail on a Lake Michigan cruise with stunning views of the city skyline. Looking for a longer adventure? Board a Great Lakes cruise ship and explore beyond the Windy City. We offer a wide range of Chicago cruises perfect for couples, families, and groups. Talk to our Trip Planners to customize your Chicago cruise experience.

Best Tours and Cruises of Chicago for 2026-2027

Explore the picturesque shoreline of Lake Superior

Great Lakes and Thunder Bay

16 Days from $9,699
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.
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Explore Toronto

All Five Great Lakes

11 Days from $6,799
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.
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Golden light over the Chicago skyline

All Five Great Lakes

11 Days from $6,799
Sail from Chicago to Toronto aboard Victory II on an 11-day cruise, exploring the best of the Great Lakes. Discover a mix of vibrant cities, quiet natural beauty, historic landmarks, and cultural icons throughout this immersive Great Lakes journey.
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Enjoy the scenery of the Great Lakes

Great Lakes and St. Lawrence Seaway

13 Days from $7,999
Sail from Chicago to Montreal on a 13-day cruise aboard Victory I, exploring iconic cities, engineering marvels, and natural wonders. Scenic lake crossings offer time to unwind between dynamic destinations.
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Historic, car-free island with lake views in Mackinac Island, Michigan

Great Lakes Treasures

10 Days from $7,995
Discover the treasures of the Great Lakes on a 10-day Viking cruise, from Milwaukee’s RiverWalk and Mackinac Island’s timeless charm to kayaking Killarney’s lakes and exploring the shipwrecks of Fathom Five. End in Chicago after hiking, wine tasting, and uncovering rich history, natural beauty, and culture along the way.
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Enjoy stunning views of Niagara Falls

Five Great Lakes and St. Lawrence Seaway

15 Days from $9,499
Sail from Chicago to Quebec on a 15-day cruise through the Great Lakes and St. Lawrence Seaway aboard Victory II. Visit iconic destinations like Mackinac Island, Niagara Falls, and Montreal. Explore vibrant cities, historic sites, and scenic waterways.
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Relax on the shores of the Great Lakes

All Five Great Lakes Reverse

11 Days from $6,799
Embark on an 11-day All Five Great Lakes cruise aboard Victory II and explore cultural hubs like Cleveland and Detroit, visit Niagara Falls, and relax on car-free Mackinac Island. Enjoy scenic days on Lake Ontario, Erie, Huron, Michigan, and Superior.
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Explore the rocky shores and clear waters of Lake Superior

All Five Great Lakes

11 Days from $6,799
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.
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Stunning Niagara Falls

Great Lakes and St. Lawrence Seaway

13 Days from $7,999
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.
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Explore the parks around Quebec City for a view of the city

Five Great Lakes and St. Lawrence Seaway

15 Days from $9,499
Explore the Great Lakes on a 15-day cruise from Quebec City to Chicago aboard Victory II. Visit Montreal, Niagara Falls, Cleveland, Detroit, Mackinac Island, and Milwaukee. Sail across Lakes Ontario, Erie, Huron, Superior, and Michigan. Experience iconic cities, rich history, scenic cruising, and cultural landmarks.
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