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Stroll through historic Chicago

Chicago City Tours

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Choose from one of these 7 City Tours to Chicago in 2023-2024 to explore the streets and take in the cityscapes of Chicago on a trip seamlessly planned by the Chicago experts at Adventure Life. Breathe in the culture, smell the local cuisine, and experience the people of Chicago on one of these extraordinary small group or private tours. Your options will likely include walking tours, bus tours, and boat tours, all led by exceptional multi-lingual local tour guides. Select any the urban exploration tours below and customize it to fit your personal interests with the help of one of Adventure Life's expert Chicago trip planners. 
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Beautiful Chicago sunset
$7,209
EXPLORE

Chicago to Montreal

13 Day Itinerary aboard Ocean Voyager
  • Discover Chicago
  • Visit the beautiful Lake Michigan
  • Cruise through Georgian Bay
  • Admire the Niagara Falls
Starts / Ends:
Chicago / Montreal
Activities:
Small Ship Cruises, Urban Exploration
Activity Level:
Relaxed
Nearly 15,000 years ago, the last of the great glaciers retreated, leaving us the five Great Lakes–Superior, Michigan, Huron, Erie, and Ontario. Together, they contain more than one-fifth of the planet’s fresh surface water. On the Ocean Voyager, delve into North America’s …
Cruise Details
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Relax on the lake shores
$5,989
EXPLORE

Chicago to Toronto

11 Day Itinerary aboard Ocean Navigator
  • Explore the cultures of Chicago
  • Enjoy views of Lake Michigan
  • Cruise through Georgian Bay
  • Admire the thundering Niagara Falls
Starts / Ends:
Chicago / Toronto
Activities:
Small Ship Cruises, Urban Exploration
Activity Level:
Relaxed
This 11-day journey from Chicago, Illinois to Toronto, Ontario explores the attractions of the Great Lakes. Discover popular ports on Lakes Michigan, Huron, Erie, and Ontario and immerse yourself in the lakes' natural splendor. The Henry Ford Museum in Detroit, Michigan, provides information on …
Cruise Details
0
Aerial views of Chicago
$7,209
EXPLORE

Chicago to Montreal

13 Day Itinerary aboard Ocean Navigator
  • Explore the cultures of Chicago
  • Enjoy views of Lake Michigan
  • Learn about American history
  • Admire the thundering Niagara Falls
Starts / Ends:
Chicago / Montreal
Activities:
Small Ship Cruises, Urban Exploration
Activity Level:
Relaxed
Discover the highlights of the Great Lakes on this 13-day cruise from Chicago, Illinois to Montreal, Quebec. Explore favorite ports of Lakes Michigan, Huron, Erie, and Ontario, and immerse yourself in the natural beauty of the lakes. Discover the history of industry and its role in the making of …
Cruise Details
0
Visit historic Chicago, Illinois
$4,259
EXPLORE

Illinois River: Chicago to St. Louis

Chicago to St. Louis - 9 Day Itinerary aboard American Countess
  • Explore the city of Chicago
  • Discover the hometown of Mark Twain
  • Find history in Peoria
  • Enjoy the natural beauty of Alton
Starts / Ends:
Chicago / St. Louis
Activities:
River Cruises, Urban Exploration, Village Visits
Activity Level:
Relaxed
Board American Countess on this 9-day cruise exploring highlights of the Illinois River. Explore the legacy of the American midwest on this river cruise through the historic heartland from Chicago to St. Louis. This journey takes you to a variety of beautiful American port cities in a luxury cruise …
Cruise Details
0
Chicago, IL
$8,889
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Roundtrip Chicago (Milwaukee)

Roundtrip Chicago - 16 Day Itinerary aboard Ocean Navigator
  • Explore the cultures of Chicago
  • Enjoy views of Lake Superior
  • Discover wonders of Houghton
  • Admire the Mackinac Island
Starts / Ends:
Chicago / Chicago
Activities:
Small Ship Cruises, Urban Exploration
Activity Level:
Relaxed
This 16-day voyage from Chicago, Illinois to Thunder Bay, Ontario, and Green Bay explores the attractions of the Great Lakes. Immerse yourself in the natural splendor of the lakes as you sail Lakes Michigan, Marquette, Thunder Bay, and back to Chicago. This extraordinary journey combines …
Cruise Details
0
Downtown Cleveland with River Bridge
$5,989
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Toronto to Chicago

11 Day Itinerary aboard Ocean Voyager
  • Explore the cultures of Chicago
  • Enjoy views of Lake Michigan
  • Cruise through Georgian Bay
  • Admire the thundering Niagara Falls
Starts / Ends:
Toronto / Chicago
Activities:
Small Ship Cruises, Urban Exploration
Activity Level:
Relaxed
Discover the highlights of the Great Lakes on this 11-day cruise from Toronto, Ontario to Chicago, Illinois. Explore favorite ports of Lakes Michigan, Huron, Erie, and Ontario, and immerse yourself in the natural beauty of the lakes. Discover the history of industry and its role in the making of …
Cruise Details
0
Enjoy stunning views of Niagara Falls
$5,989
EXPLORE

Chicago to Toronto

11 Day Itinerary aboard Ocean Voyager
  • Discover Chicago
  • Enjoy views of Lake Michigan
  • Cruise through Georgian Bay
  • Admire Niagara Falls
Starts / Ends:
Chicago / Toronto
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration, Wine Tasting
Activity Level:
Relaxed
On this 11-day journey of the Great Lakes aboard the Ocean Voyager, delve into the nautical history of North America. Your vacation begins in Chicago, Illinois, a vibrant city with a strong arts scene, a rich history, and a variety of cuisines. Set sail on Lake Michigan for a Great Lakes cruise, …
Cruise Details
0
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