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Illinois

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Select one of the below 19 best Illinois trips for 2026 and 2027. Your local English-speaking guide will lead your small group or personalized private tour on an extraordinary adventure exploring Chicago, Lake Michigan, Alton, and Mississippi River. Our Illinois trips for 2026 feature Urban Exploration, Archaeological Site Visits, Biking, Local Market Visits, and Village Visits, and start from $4,610 for trips of 9 to 16 days. Contact Adventure Life's Illinois trip planning experts to start planning your next seamless trip.
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    • Illinois
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
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
Golden light over the Chicago skyline
from $6,799
EXPLORE

All Five Great Lakes

Chicago to Toronto - 11 Day Itinerary aboard Victory II
  • Visit Chicago’s Art Institute
  • Sail scenic Lake Michigan
  • Discover Milwaukee city
  • Visit Niagara Falls
Starts / Ends
Chicago / Toronto
Activity Level
Variable
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.
Cruise Details
0
Enjoy the stunning scenery of Lake Superior
from $7,499
EXPLORE

All Five Great Lakes

Chicago - Toronto - 11 Day Itinerary aboard Victory I
  • Lake Michigan crossing
  • Stroll Milwaukee Riverwalk
  • Visit Cleveland Rock Hall
  • Niagara Falls visit
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
Mackinac Island, Michigan
from $7,299
Save $4000
EXPLORE

All Five Great Lakes

Chicago to Toronto - 11 Day Itinerary aboard Victory II
  • Explore Navy Pier and city skyline
  • Visit Milwaukee craft breweries
  • Lake Michigan sailing
  • Enjoy Escanaba waterfront views
Starts / Ends
Chicago / Toronto
Activity Level
Variable
Embark on an 11-day Great Lakes cruise aboard Victory II from Chicago to Toronto. Explore Detroit, Cleveland, Mackinac Island, Niagara Falls, and Milwaukee. Sail Lake Michigan, Huron, and Superior. Participate in cultural programs, enjoy scenic decks, and witness engineering marvels at the Soo Locks.
Cruise Details
0
Look for the lighthouses of the Great Lakes
from $9,570
$1000 SBC
EXPLORE

A Voyage Along the Great Lakes – with Smithsonian Journeys

Toronto - Milwaukee - 9 Day Itinerary aboard Le Bellot
  • Discover Toronto’s diversity
  • Explore Port Colborne beauty
  • Navigate Detroit River panoramas
  • Cruise Lake Michigan grandeur
Starts / Ends
Toronto / Milwaukee
Activity Level
Variable
Set sail on a 9-day cruise aboard Le Bellot to uncover the Great Lakes' stunning landscapes and rich history. Highlights include Niagara Falls, Lake Huron's UNESCO Biosphere Reserve, Mackinac Island's Victorian charm, and Milwaukee's vibrant culture, making this an unforgettable journey.
Cruise Details
0
Enjoy stunning views of Niagara Falls
from $9,499
EXPLORE

Five Great Lakes and St. Lawrence Seaway

Chicago to Quebec - 15 Day Itinerary aboard Victory II
  • Cruise scenic Lake Huron
  • Explore old Montreal
  • Experience Detroit’s rich heritage
  • Witness Soo Locks engineering
Starts / Ends
Chicago / Quebec City
Activities
Local Market Visits
Activity Level
Variable
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.
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
  • Niagara Falls visit
  • See Cleveland Rock Hal
  • Observe Soo Locks transit
  • Mackinac Island cycling
Starts / Ends
Chicago / Montreal
Activity Level
Variable
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.
Cruise Details
0
Explore Toronto
from $7,299
Save $4000
EXPLORE

All Five Great Lakes

Chicago to Toronto - 11 Day Itinerary aboard Victory I
  • Explore Mackinac Island by bike
  • Lake Huron sailing
  • Learn Detroit creative revival
  • Experience Niagara Falls
Starts / Ends
Chicago / Toronto
Activity Level
Variable
Sail the Great Lakes on an 11-day cruise aboard Victory I, exploring Chicago, Milwaukee, Mackinac Island, Detroit, Cleveland, Niagara Falls, and Toronto. You experience historic locks, island cycling, cultural cities, and scenic lake passages across interconnected inland seas.
Cruise Details
0
Historic, car-free island with lake views in Mackinac Island, Michigan
from $7,995
EXPLORE

Great Lakes Treasures

Milwaukee to Milwaukee - 10 Day Itinerary aboard Viking Great Lakes
  • Stroll Milwaukee RiverWalk
  • Ride Mackinac Island Carriage
  • Explore shipwrecks & cliffs
  • Discover Soo Locks History
Starts / Ends
Milwaukee / Milwaukee
Activities
Hiking, Fishing, Citizen Science, Kayaking, Scuba Diving
Activity Level
Variable
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.
Cruise Details
0
Visit the Quad cities, including Davenport, Iowa
from $5,635
Savings
EXPLORE

Upper Mississippi River

St. Louis, MO to St. Paul, MN - 9 Day Itinerary aboard American Melody
  • Explore the culture of St. Louis
  • See Mark Twain's hometown, Hannibal
  • Experience wildlife and nature
  • Admire local artwork in Red Wing
Starts / Ends
St. Louis / Red Wing
Activities
Cooking Classes
Activity Level
Variable
Explore the Upper Mississippi River on this 9-day cruise from St. Louis to Minneapolis aboard the American Melody. Begin in St. Louis, Missouri, and travel through Alton, Hannibal, Muscatine, Dubuque, Winona, and Red Wing. Visit Mark Twain's boyhood home, explore historic towns, and marvel at the diverse landscapes.
Cruise Details
0
Vibrant Sunset with St. Paul City Skyline and Mississippi Riverfront
from $5,635
Savings
EXPLORE

Upper Mississippi River

St. Paul, MN - St. Louis, MO - 9 Day Itinerary aboard American Serenade
  • Tour historic Summit Avenue
  • Explore Dubuque River Museum
  • Experience John Deere Pavilion
  • Visit Mark Twain’s boyhood home
Starts / Ends
St. Paul / St. Louis
Activities
Wine Tasting, Village Visits, Archaeological Site Visits, Urban Exploration, Biking, Wildlife Viewing
Activity Level
Variable
Set sail for 9 days aboard American Serenade from St. Paul to St. Louis. Walk through historic Summit Avenue, admire La Crosse from Grandad’s Bluff, explore Dubuque’s River Museum, and discover Mark Twain’s legacy in Hannibal. Experience curated onboard programs, live music, and the beauty of the Upper Mississippi’s diverse wildlife.
Cruise Details
0
Explore the rocky shores and clear waters of Lake Superior
from $6,799
Save $4000
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
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Cruise the Mississippi River on your small ship cruise
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